Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

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—

I grew up playing a lot of tennis. My semi-western forehand is older than most of my friendships. I don’t get out as much as I’d like these days, but every June the long tennis summer opens up in front of me. Roland Garros, then breakfast at Wimbledon, then night matches at the US Open. I get pulled back in. I never talk during a tiebreak.

Lately I’ve been thinking about Andy Roddick.

Twenty years ago, Roddick limped out of the French Open in the first round. He’d rolled his ankle the week before, taped it heavily, and retired early in the third set, down two sets to love, hobbling off Court Suzanne-Lenglen to boos from the Paris crowd. It was the fifth seed’s third first-round exit in six trips to Roland Garros, the major that never liked him back. A month later he hired Jimmy Connors.

The ankle healed. The thing underneath it didn’t. Roddick’s game had gone flat, and he knew it: too conservative on the points that mattered, leaning on his serve to bail him out instead of going forward and taking the point himself. He wanted to play with some teeth again. Connors had built a whole career on teeth, which made him an obvious choice, and an unconventional one. Connors had never coached.

But wanting that and knowing how to get there turned out to be two different things. Roddick showed up to one of his early sessions expecting to get straight to it. Connors stopped him before he’d hit more than a few balls. By Roddick’s own account, he roasted him.

“In the first ten minutes, your footwork is average. Tour average at best.”

And the berating continued. The ball’s coming slow right now, he said, so why aren’t you using it to get the reps in, before everything speeds up and you can’t?

Those first ten minutes are a free run at proper footwork. The ball’s slow, nothing’s riding on it, and it’s the only window you get before the match starts making you pay for getting it wrong.

Roddick had hired a coach to fix his attack. Connors looked at his feet.

What Connors Saw

Roddick was no beginner. He’d been near the top of the sport for years, coached and analyzed by people who understood it cold, and he had a clear read on his own problem. The read wasn’t even wrong. He was passive. But the cause of it lived in a place he’d never thought to check. You don’t get to swing hard at a ball you’ve reached a half-step late. The footwork happened first and set the terms for everything after it.

His footwork wasn’t broken. That was the trap. It was good enough, every day, which is exactly why no one — including him — ever thought to look at it. It happened in the moment before the part anyone watches. And against the best movers in the game, Federer chief among them, it was the difference between getting set to do damage and getting pulled off the court before he could.

I had the same blind spot, on a much worse court. As a kid in lessons I wanted a bigger serve and a cleaner backhand. I wanted the shot you’d remember. Nobody fantasizes about footwork. It’s the part you’d skip if anyone let you, so I skipped it, and I stayed mediocre in a way I couldn’t explain and never thought to interrogate. To this day, when I meet someone who played a lot growing up but hasn’t picked up a racquet in years, I notice two things. The swing is still there. They never lose that. But the footwork is rusty. Timing and movement are the first to go.

Tour Average

That might be a compliment to you and me, but it wasn’t one for Andy. He’d been number one in the world, and the piece of his game Connors pulled out was, next to everyone else on tour, completely ordinary. Tour average. The plainest part of an elite player’s game, and the thing holding his ceiling in place.

Roddick put it this way on a podcast: “I have seen some bad players by tour standards — ball strikers, don’t serve big, can’t go through you — but they have great footwork... there have been top 100 players in the world because of it.”

Footwork with nothing else attached, enough to make you a pro. Which cuts both ways. If it can carry a player with no weapons, it can just as easily cap a player who has all of them.

And if it’s just working well enough, you might never see it. That’s the strange part about this kind of weakness. It isn’t a hole you fall into. It’s something you do passably, every day, so smoothly that it never lands on a list of things to fix.

Which is why it almost never shows up as a footwork problem. It shows up as a swing problem.

Watch the Feet

Imagine you’re walking into a meeting you’ve walked into fifty times. Maybe it’s the weekly review where one person always seems to walk off with the credit for work you did. You know how it goes before it starts. You’ve half-rehearsed your part in the shower, the small defense already loaded for when it comes up. You walk in a little braced, shoulders already up around your ears. And the meeting goes the way it always goes, which is to say the way you walked in expecting it to.

Now imagine the one time it didn’t. Maybe you were running late and never got the chance to wind yourself up. Maybe you’d spent five minutes beforehand actually talking to the person instead of bracing against them, working out who would cover what. And it went better than it had ever gone. If you stop and ask yourself what was different that time, it’s almost never the slides or the points you made. It’s that you walked in without trying to prove anything.

That’s your footwork. Not the meeting itself, but how you arrived at it.

The hardest part? Even once you can see it, you can’t fix it in the moment. By the time you’re in the room with your heart going, the footwork is already set. You can’t groove a new way of arriving while the match is live and everything’s on the line. You can only do that earlier, when the ball is slow.

Now take something with more at stake. You’re interviewing for a job you want. You’ve done the prep, you’ve got your stories ready and your answers polished, because the answers feel like the part you can control. And you keep not getting the offer, and you can’t work out why, because the answers are good.

But go back to the second you sat down. What were you actually trying to do in that conversation? If the honest answer is get the offer, your feet were wrong before you said a word. The moment you walk in needing to walk out with something, you stop finding anything out. You start performing. You field every question like a test instead of asking the ones that would tell you whether you even want the job. The person across the table can’t name what’s off about you. They just feel it, the way you can feel when someone’s selling you something.

The fix was never a sharper answer. Same room, same résumé, different feet.

The Slow Ball

Roddick never won the French Open. But the summer he hired Connors, the one that started with him limping off to boos, ended with a run to the US Open final. He lost there too, to Federer, the way he usually did. He’d just moved differently to get there. He came forward. He started taking points instead of waiting around for them, which was the whole reason he’d called Connors in the first place. He got there through his feet.

I keep picturing Connors stopping him in those first ten minutes, not to fix the serve or rework the tactics, but to point at the ground during the easy part and ask why he was wasting it.

The slow ball is a gift. Most of us swing right through it.

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

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—

More than a decade ago I started falling asleep to podcasts. Politics, sports, the occasional interview show. I told myself I was winning — carving out time I didn’t have during the day. Somewhere between awake and asleep. Peak multitasking.

Back then the app stopped after the episode ended. I’d probably remember the first twenty minutes. The app has “evolved” since. It auto-plays now. It never stops. There’s someone talking in my ear while I sleep, every night. My wife eventually bought me a pair of sleep earbuds, designed for the side sleeper, so the arrangement would be more comfortable.

I’m still wearing them.

Picture the week the calendar finally clears.

An AI workflow cuts the team’s documentation cycle from a week to a day. A reorg settles the same week. For about ten days, the calendar looks like what it was always supposed to look like.

A leader I work with described the feeling like this: “Coming back from Yosemite. Like a fresh laptop with no files.”

I laughed. He didn’t, really. In those ten days he’d built two things he’d been thinking about for months. He’d had a conversation he’d been meaning to have for longer than he could remember. He’d noticed a subtle friction in how his team was moving — something he couldn’t name until suddenly he could — and acted on it before it hardened into a problem.

Then the meetings came back.

“I keep wondering,” he said, “if that ten days was the most useful thing I did all quarter.”

What We Put on the Calendar

Claude said music is the space between the notes. Debussy, that is — though I have a feeling that’s not the first Claude that comes to mind these days. The line has lived a hundred lives, but Debussy used it to describe something specific: the difference between music and just filling silence. He wasn’t talking about rests or pauses. He was talking about intention. What you don’t play shapes what you do. Emptiness, handled well, is its own kind of work.

I’ve been turning that idea over lately, applying it to something I see constantly in coaching: the belief that the most important work is the work on the calendar.

It isn’t.

In coaching, we tell clients this directly. The session, fifty minutes on a Tuesday, is not where the change happens. It’s where the conversation starts. The actual work comes after: the thing you notice on Wednesday that you wouldn’t have noticed Monday, the decision you make differently because a question is still rattling around in your head, the pattern you finally see in yourself after sitting with it for three days. I can always tell when a client is doing that work between sessions. They come back different. Not better prepared. Different. Something has moved.

The session is the note. The space between is the music. The plan anticipates. The between-time discovers.

Activity Is Not Learning

A different version of this shows up in coaching all the time. Someone arrives looking to leave a job that’s stopped teaching them anything, with the kind of energy that’s its own warning sign — wanting to do everything, immediately, in volume.

One leader I worked with sent me a status update between sessions I had to read twice. He’d built an AI-powered prep pipeline for his job search — research synthesized, briefs generated, learning modules assembled, agents running while he slept. By any conventional measure, an industrial operation. It was impressive.

I asked him what he’d learned from any of it.

He paused. Then he listed the artifacts again.

“Those are activities,” I said. “I’m asking what you learned.”

It took him a minute. He’d built something that could produce at scale, and the act of producing had become its own answer. The throughput felt like progress. The harder work the search actually requires was harder to see. The part where you sit with what you actually want, why this company and not that one, what kind of leader you want to become.

Now imagine someone training for a marathon. After every long run, they can tell you exactly what they’d do differently next time. Slower opening pace. Earlier electrolytes. Different shoes for the hills. They iterate the way runners iterate — small experiments, named adjustments, an answer that gets sharper each pass.

That’s learning. The job search version was just generating.

Human Beings, Not Human Doers

The pattern is everywhere. Podcasts on the commute. Voice notes between meetings. One leader I work with told me he listens to a podcast at his kid’s softball game, just to stay productive during the downtime — and when I asked what happened in the game, he had to think about it.

I recognized the move. I do my own version every night, with the earbuds in. And in the morning on the train, when I could be looking out the window. And on the walk to drop my kid at school, when she’s quiet and I could be too. The idle moment shows up and I fill it. Not because I’m choosing to — because filling it has become the default, the path of least resistance, the thing that happens before I notice I’m doing it.

We are human beings, not human doers. I say this to clients more than any other single line, and it lands differently every time. Sometimes as a laugh. Sometimes as something heavier.

Insight delivered in a session rarely does the work by itself. The integration happens after — in the shower, on a walk, in the quiet before sleep when something clicks. It just requires space.

Most of us aren’t leaving any.

What AI Is Quietly Surfacing

The situation has changed, and I don’t think we’ve fully reckoned with it.

AI is very good at producing artifacts. Roadmaps, strategies, specs, summaries — outputs that used to require hours of focused work can now be generated in minutes. For a lot of leaders, this is landing as relief. Less time in the document, more time for the work.

My podcast app did this first, on a smaller scale. It used to stop. Now it doesn’t. Nobody asked me whether I wanted more — the natural stopping point just disappeared.

I’m not sure the space is opening up the way we think it is.

When it costs almost nothing to produce a roadmap, you produce more roadmaps. When the artifact is cheap, the instinct is to fill the recovered time with more artifacts. More plans, more structured output, more things that feel like progress because they exist and can be shared.

I asked the same leader what he did with the other four days.

“I built a better template for the next documentation cycle,” he said.

The space didn’t open. He just filled it differently.

This is a second-order effect. AI isn’t automatically buying us more between-time. It’s handing us more capacity that our instincts immediately convert back into output. If the problem is that we mistake the artifact for the work, making artifacts cheaper doesn’t solve the problem. It accelerates it.

What AI Can’t Do

A founder I coach was acquired recently by one of those wildly popular, fast-growing AI-native companies. He told me how they define a PM’s job — the whole job, not the listed responsibilities. Can this person pitch an idea that gets the entire company excited? That’s it. If the idea is compelling enough, prioritization and scoping get solved by motivated people. The PM’s job isn’t to manage the artifacts. It’s to generate the conviction that makes them move.

When AI can produce the deck and the spec and the summary of the summary, what’s left is the thing AI can’t generate: the conviction that comes from someone having sat with a problem long enough to know it cold.

I asked another client recently how he makes big decisions. He thought about it and described a process I keep coming back to. It starts as a feeling, he said. Sometimes a kind of low-grade unease, sometimes excitement. It builds for weeks. Occasionally it shows up in dreams. From that signal, eventually, a direction emerges — clear enough that he can name it. Then come the questions. The research. The probing conversations. The slow accumulation of certainty. By the time he commits, he isn’t deciding. He’s recognizing.

That’s the shape of conviction. It starts in the body. It takes time. It can’t be skipped. AI can compress every step that comes after the recognition — research, drafts, options, frameworks. But it can’t compress the part where you have to sit with the unease long enough to know what it’s telling you. That’s the irreducible part. That’s the part that lives in the between.

AI can produce the deck and prototype. It cannot produce the person who can stand up and defend it.

What to Do Instead

A warning, though. Reflection isn’t always pleasant. When you stop filling the gap, the gap is where the discomfort has been hiding. Naming what’s missing tends to make the frustration worse before it makes it better. That’s progress. It’s also why the in-between is uncomfortable enough that we’ll happily fill it with another roadmap.

The way out isn’t a better roadmap. It’s a different question.

The one I ask most isn’t what happened? — that’s too easy to answer with reportage, with a list of meetings and tasks. It’s what changed? What’s different about how you’re seeing this compared to two weeks ago? That question surfaces work that was happening in the background. And it’s almost always where the most useful part of a session comes from. Not the prepared agenda. The thing that shifted in the between.

The Fresh Laptop

He came back a few weeks later and told me he’d started protecting the first hour of his Thursday mornings. Nothing on the calendar. No agenda. Just a cup of coffee and whatever he was actually thinking about.

“It feels indulgent,” he said.

“Does it feel useful?”

He thought about it. “More than most of my meetings.”

The space between doesn’t announce itself as important. It doesn’t produce a deliverable you can show someone. It doesn’t make the roadmap. It just quietly does most of the work.

Miles Davis could fill every silence. He had the chops for it. He chose not to, because he understood the silence was load-bearing. What you leave out shapes what you put in.

The space isn’t emptiness. It’s structure.

—
Note: Stories from coaching sessions are used with permission and identifying details have been changed.

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

Join my referral program and earn 1:1 coaching sessions by sharing Frank Takeaways with others - start with just three referrals.
—

I was making a vinaigrette last Tuesday when my four-year-old asked if she could help. I handed her the whisk and she went at it. Aggressive, cheerful, completely wrong. Oil everywhere, mustard on the counter, vinegar pooling near the edge. I started to correct her technique, then stopped. She wasn’t learning to make vinaigrette. She was learning what happens when you combine things.

What separates a feature that works from a feature that feels right? That magical product taste. Every hiring manager says they want it but nobody can quite define it in a job description. We talk about it like it's a personality trait, something you either have or don't. I think that's wrong. It's an output.

We say it’s the human quality that AI can’t replicate, the last moat. Maybe. But if taste is an output, the models will get better at it too. Which is exactly why it’s worth understanding what the inputs actually are.

I’ve been building products and teams for twenty years and to this day, I always use some variation of the same question when interviewing candidates. I want to find out if they’re a product curmudgeon and an internal optimist for making things better. I look for taste. “Tell me about the worst product you’ve ever used.” “Tell me about the best product.” “How would you make it better? What would you do first?”

The stratification of answers unearths taste in short order. So what are the inputs? I think there are three.

Curiosity

You can’t develop taste in isolation. You need to use a lot of products, and not just the ones in your category or the well-known ones. You need to use bad products, too. Especially bad products.

When I was a UX designer at Google in the early days, I was using probably thirty or forty different web products a week. Not all of them were research. Most of it was just living on the internet. I remember Rdio, the music streaming app that died in 2015. It was better than Spotify in almost every way that mattered to me: the typography, the social features, the way it handled queuing. It lost anyway. But using it taught me something about the difference between a product that’s correct and a product that someone loved making. You could feel the care. I still think about Rdio’s album grid when I’m reviewing designs.

That volume built something. I started recognizing patterns before I could name them. I’d open a new tool and know within ten seconds whether the person who built it had thought carefully about the first three minutes of use. I couldn’t always tell you why. It was a feeling, like recognizing a chord change in a song even if you can’t name the key.

Volume of contact builds the library your intuition draws from. If your library is small, your intuition is shallow.

But curiosity isn’t just breadth. It’s also depth. At Betterment, I used our own product to manage my actual money. Not a test account. Real deposits, real transfers, real anxiety when the market dropped. When it’s your money, you notice the three-second delay on the portfolio page differently. That kind of friction doesn’t show up in any funnel chart. You have to live inside the product long enough to feel it.

I also signed up for every major competitor with real money and gave my entire team access to the accounts. Wealthfront, Wealthsimple, SoFi, all of them. I wanted everyone to feel what it was like to be a customer somewhere else, to notice where we were better and where we were embarrassingly behind. It was useful. It was madness come tax season.

The people whose taste goes stale are the ones who stop being curious. They found their aesthetic and their framework and their opinions, and they stopped looking. They coast on pattern recognition built years ago, and slowly, without noticing, their instincts fall behind. Curiosity is the engine. Without it, everything else decays.

But noticing what’s good isn’t the same as knowing how to make something good.

Craft

Almost everyone I know who has great product taste also makes things outside of product work. They cook, play music, build furniture, write. The specific discipline doesn’t matter. What matters is that they’ve experienced the gap between what they imagined and what they made, over and over, and they’ve learned to close it.

I enrolled in the bread course at the International Culinary Center a few years ago. COVID cancelled it before I ever walked in. But I’d already gone deep into baking on my own, and the obsession taught me something about product that no sprint retrospective ever did. In bread, you can’t fake it. The dough tells you immediately whether you paid attention during bulk fermentation. There’s no A/B test for a baguette. There’s just the crumb, and you know whether it’s right.

That sense of knowing-whether-it’s-right carries over. Once you’ve calibrated your senses in one domain, you start expecting the same level of care in others. You walk into an app and you can feel whether someone shaped it with attention or just shipped what compiled.

Katie Dill, Stripe’s head of design, put it well: things that are more beautiful increase trust. You see the painstaking detail, and it gives you assurance that they care about other details you can’t see. She’s describing what taste produces. But the thing that produces it is someone who knows what care feels like because they’ve practiced it somewhere.

Conviction

Having taste requires having a point of view. You have to be willing to say “this is bad” and “this is good” and “here’s why,” out loud, on the record, before you know how the thing performs. Taste without conviction is just observation.

But conviction alone is dangerous. I’ve watched brilliant leaders hold onto opinions long past the point where the evidence turned against them, because the opinion had become part of their identity. The fix isn’t less conviction. It’s a feedback loop. Annie Duke talks about this: making your implicit judgments explicit so you can find out when they’re wrong. Your intuition is sometimes right. But if you never surface it, you never learn when it isn’t.

Let’s call her Marta. She was a product director I coached last year. Incredibly smart, strong opinions about everything. Her team loved her conviction until they didn’t. It wasn’t that she was wrong more than anyone else. She just never tracked when she was wrong, so she never updated. I suggested she start a decision log. Nothing elaborate, just a note every time she made a product call: what she decided, why, what she expected to happen. Every quarter, she’d review it. Three months in, she started catching her own blind spots. Her opinions didn’t get weaker. They got more accurate.

Conviction also means knowing what to remove. At Etsy, I was known for killing features. It became a Friday ritual. Most of the time nobody noticed, and what was left got better. Shopify has something called the Delete Code Club where they regularly find a million-plus lines of code to cut. That’s not cost-cutting. That’s curation.

Aparna Chennapragada, Microsoft’s CPO, made this point recently: in a world where AI makes the supply of ideas and prototypes an order of magnitude higher, the editing function is what matters most. When everyone can generate, the value shifts to the person who knows what to keep and what to kill.

Before the World Ends

If taste is learnable, then it’s also teachable. Look, maybe the models do get good enough at taste that half of this becomes moot. In the meantime, here’s what I’d do right now, whether you’re trying to sharpen your own or raise the bar for your team.

Tinker. This is the most important one. Not efficiency. Not “AI adoption.” Actual unstructured exploration where 80% of what you try fails. If you’re a leader you have to create space for your team to do this — and you need to do it too. The first two months might feel like a loss. That’s how it’s supposed to feel.

Use something new every week. Not a demo. Actually use it. Sign up, put real data in, hit the edges. Write down what you notice. Your intuition library only grows when you feed it.

Make something with your hands. Cook a meal from scratch. Build a shelf. Write something that isn’t a PRD. The point isn’t the output. It’s training yourself to feel the gap between what you intended and what you made.

Start a decision log. Every product call you make, write down what you decided and why. Review it quarterly. You’ll be shocked how quickly your blind spots reveal themselves.

Kill something. Look at your product, your roadmap, your backlog. Find the thing that’s technically fine but not actually good. Remove it. See if anyone notices. They probably won’t.

My daughter eventually got the vinaigrette mixed. It was lumpy and oversalted, and she insisted on tasting it straight from the bowl with a spoon. She made a face, thought about it, and said, “More honey.”

She was right.

You just have to keep combining things and noticing what happens when you do.

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

Join my referral program and earn 1:1 coaching sessions by sharing Frank Takeaways with others - start with just three referrals.
—

A coaching client asked me a question last week:

“What are your thoughts on the emerging ‘full stack builder’ PM model — what do you think about it and what does it mean for product leadership?”

I started typing a response and then stopped. Deleted it. Started again. The question sounds simple but it’s actually three questions tangled together: Is this real? Is it new? And what should leaders do about it?

I’ve been turning it over for days. Here’s where I’ve landed.

The Skeptic's Take

My first instinct was skepticism. I've been in product long enough to see trends come and go. Every few years, someone announces a new model for what PMs should be. T-shaped PMs. Technical PMs. Growth PMs. Now full-stack builder PMs.

So I asked myself: is this actually different from what strong PMs have always been?

Not entirely.

When I hire PMs, I've always looked for one or two hard execution skills. Product management is a leadership discipline, and the best leaders flex to the needs of their team. The deeper skills you have, the more ways you can flex. Former engineers who can debug. Former designers who can mock up solutions. Former analysts who can dig into metrics.

The "full stack builder" is just another station. Useful? Sure. Revolutionary? I'm not convinced.

But Something Is Different

Here's where I have to check my own skepticism.

The tools have changed. Meaningfully. Cursor, Claude Code, Lovable, Replit. These aren't incremental improvements. A PM can now go from idea to working prototype in an afternoon. Not a mockup. Not a spec. Working code that users can touch.

I know because I'm doing it. After my kids go to sleep, I ship real features to real products. Small SaaS tools I've built. Recipe apps. Practice management software. Not prototypes. Production code. A few years ago this would have required hiring engineers or learning to code properly. Now I can build things I couldn't have built before.

That's not nothing.

Asha Sharma put it well on Lenny's podcast recently: "It's all about the loop, not the lane." The old model was lanes. Design stays in their lane, engineering in theirs, PM in theirs. Work moves linearly through the system. The full stack builder collapses that. You own the whole loop: idea to build to user feedback to iteration. No handoffs. No tickets. No waiting for the next sprint.

When the loop gets tighter, learning gets faster. And learning is the whole point of shipping in the first place.

So yes, something is different. The cost of building has dropped. The speed of iteration has increased. More people can participate in the build cycle than ever before.

But I keep coming back to a question: does faster building actually make better products?

The College Town Theory

There's this thing that happens in college towns. The commerce district turns over constantly. New restaurants open, old ones close. The names change. The decor changes. The menus change.

But somehow it's still a lot of bars.

The surface changes, but the underlying structure stays the same. Students want cheap drinks and late nights. The market demands what the market demands.

Product management feels similar to me right now.

The tools are new. The speed is new. The "full stack builder" framing is new. But the underlying job hasn't changed. You're still trying to figure out what problem to solve. You're still trying to design a solution that works. You're still trying to ship something that creates value for users and for the business. You're still trying to learn from what happens and do it better next time.

The loop is faster. But it's the same loop.

This matters because I see people confusing speed with progress. A PM who can ship twelve features in a quarter feels productive. But if none of those features moved the needle, what was the point? You can iterate yourself in circles.

The hard part of product management was never the building. It was knowing what to build. That hasn't changed.

What Leaders Actually Need

The question was about product leadership, so let me try to answer that directly.

If you're leading a PM team right now, here's what I'd focus on:

Hire for judgment, not just execution. Yes, it's great if your PMs can prototype. But prototyping is a skill you can teach in weeks. Judgment takes years. The ability to look at a problem and know which parts matter. The ability to make a call with incomplete information. The ability to recognize a bad idea before it's built. These are the hard things, and they're the same hard things they've always been.

I still interview for hard skills. I still want PMs who can do things beyond the core PM toolkit. But I'm more interested in how they think than what they can build. Show me a candidate who can ship a prototype in an afternoon but can't articulate why that's the right problem to solve, and I'm worried. Show me a candidate who asks uncomfortable questions about whether we should build something at all, and I'm interested.

Close the learning loop. Here's where I see full stack builders get into trouble: they ship, then immediately ship again. The build cycle is so fast that they skip the learning part. They iterate without reflecting. They optimize without questioning.

Shipping is the best way to learn. It always has been. But only if you actually learn. That means talking to users after you ship. It means asking "what did we expect to happen and what actually happened." It means having someone challenge your interpretation of the results, not just your spec before you built it.

The friction shouldn't come before the build. It should come after. Build fast, ship fast, then slow down long enough to understand what you learned. Then build again.

Teach the strategy work explicitly. Vision, strategy, roadmap. These don't emerge automatically from shipping fast. They require a different kind of thinking. Zooming out instead of zooming in. Asking "why this and not that" instead of "how do I build this." If your PMs are heads-down in execution all the time, when are they developing this muscle?

I've started asking my coaching clients a simple question: what did you learn from the last thing you shipped? Not what did you build. What did you learn. Half the time they can't answer. They've already moved on to the next thing. The strategy muscle atrophies if you don't use it, and execution can feel like progress even when you're just spinning.

Model the curiosity. The best product leaders I know are tinkering with these tools themselves. Not because they need to ship code, but because they need to understand what's possible. You can't lead a team through a shift you don't understand firsthand. You don't need to become a full stack builder yourself. But you do need to know what your team can now do that they couldn't do before.

The Question I'm Still Sitting With

Here's where I landed. The full stack builder trend is real, but it's more evolution than revolution. The tools have changed. The speed has changed. But the core discipline hasn't.

Product leadership is still about solving the right problems. Still about building teams that can execute with judgment. Still about creating clarity in ambiguity. None of which are solved by knowing how to code.

The risk isn't that PMs are building too fast. Speed is a gift. The risk is that they're shipping without learning. Iterating without reflecting. Moving on to the next thing before they've understood the last thing.

But here's the question I keep coming back to: How do we develop judgment and taste when the loop is this fast? The answer, I think, is that you develop it through the loop, not before it. You build, you ship, you learn, you get challenged on what you learned, and then you build again. The reps compound. But only if you're actually closing the loop.

The names change. The tools change. The discourse changes.

But at the end of the day, you're still trying to solve someone else's problem. That part hasn't changed. And if you lose sight of it, all the building speed in the world won't help you.

Still a lot of bars.

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

Join my referral program and earn 1:1 coaching sessions by sharing Frank Takeaways with others - start with just three referrals.
—

I watch a lot of sports. Grew up playing them. They were always on in my house, a backdrop to every holiday, different teams and vintages discussed like distant relatives. Sports is drama — there is no script — and it changes year to year.

So does the scorebug.

A scorebug is the graphic overlay on a broadcast that displays the score, the clock, the teams. It seems simple, but someone designs it. Someone decides what information matters most in this moment. During the Olympics, scorebugs feature flags — nationality is the story. This year’s NFL broadcasts prominently feature team mascots over names — identity and brand are the story. The scorebug orients millions of viewers on what to focus on and why.

Products have scorebugs too. So do careers. Someone is always deciding what numbers to put on screen. The question is whether it’s you or someone else.

At Betterment, customers had chosen their own scorebug — and it was grading the wrong thing. Deposits surged when the market was up. They slowed when the market was down. People were evaluating us the same way: deposit $10k, wait 90 days, check if they had more or less.

The problem? That test graded the market, not us.

We could build the most sophisticated rebalancing algorithms, harvest tax losses automatically, optimize portfolios around the clock. None of it mattered if the only question customers asked was “did my number go up?”

This wasn’t broken yet. During a bull market, deposits were strong. But winter was coming. It always is. The best time to fix this was while we had room to experiment. It was also the hardest time to make the case, because nothing felt urgent.

So we started seeding a different scorecard.

We reframed our value around the work we did constantly on your behalf: rebalancing, tax efficiency, portfolio adjustments. We pulled that language forward into landing pages, onboarding flows, and regular emails. “Here’s what we did for you this month. Here are the trades we executed. Here’s the tax loss we harvested.”

Without this, customers had a single metric: more money or less. We gave them a larger scorecard. One that reflected what we actually did well, not just what the market happened to do.

The Loudest Metric Wins

Here’s the uncomfortable truth: if you don’t define how you’re evaluated, people will default to the most obvious metric. Not because they’re lazy or unfair, but because evaluating anything is work. After all, people care way less about your product than you do. People reach for the simplest measure available. At Betterment, that was account balance. Easy to check, easy to compare, completely outside our control.

Staying vague about your goals feels safer. If you don’t commit to specific metrics, you can’t be held to them. But vagueness doesn’t protect you. It just means someone else picks the test. And they’ll pick the one that’s easiest to grade, not the one that captures what you actually do.

You don’t avoid being evaluated by staying quiet. You just lose control of the scorecard.

When the Game Becomes the Metric

I saw a more dramatic version of this at Etsy.

When I arrived, search results were sorted by recency. Sellers paid a small fee to list items for four months. Savvy sellers figured out that relisting early would bump them back to the top. It worked, and Etsy collected more fees. This premature relisting drove a non-trivial amount of company revenue.

But the more sellers adopted this tactic, the less effective it became for everyone. Sellers who couldn’t afford to constantly relist found themselves trapped at the bottom of search results. We hadn’t designed it this way — we’d simply given sellers a tool, and the savviest ones turned it from an advantage into a requirement.

Winter was coming again. Finance and Product were both nervous, but getting alignment to change something driving revenue wasn’t easy. We had to move while the numbers still looked good.

We improved search relevancy so gaming recency mattered less. We introduced promoted listings that sellers could purchase. And critically, we gave sellers analytics to see how their promotions actually performed.

Before, sellers had a gut feeling: “relisting seems to help.” We replaced the hunch with a scorecard. Real data on what was working and what wasn’t. We didn’t just change the product. We changed how sellers evaluated their own success.

The Test That Wasn’t About the Decision

The hardest version of this isn’t product strategy. It’s leadership.

A client I coach — let’s call him David — came to me after his first quarter in a senior role. He’d made some deeply unpopular calls. Restructured teams. Let people go. The kind of decisions that ripple through hallways and Slack channels for weeks.

“Everyone hates me,” he said. Not self-pity — just an observation. Town halls had a new silence. People asked polite questions but nothing real.

He didn’t try to convince anyone the decisions were popular. He didn’t argue that people should feel differently than they felt. Instead, we worked on defining a different scorecard.

He told his team he was there for the long haul. He asked them to evaluate him in six months. Not on whether they liked what he’d done. Not on whether they were still upset. On whether the company was in a better position.

Six months later, it was. People could see the results, even if they hadn’t loved the path.

David understood something important: after a hard decision, the loudest metric is pain. If you let that be the scorecard, you’ll fail it every time. His job wasn’t to eliminate the pain. It was to give people a different test to grade him on.

This isn’t just a C-suite move. Anyone making a bet on themselves faces the same dynamic: a PM going up for promotion, a product leader pitching a risky roadmap, a founder asking investors for patience. You’re asking people to believe in a future they can’t see yet. The loudest metric — what’s visible today — will win unless you seed a better one.

The Scorecard That Shaped the Roadmap

Seeding a scorecard doesn’t guarantee the outcome you want.

At Betterment, deposits didn’t surge after we reframed our value. Money is personal and irrational. People don’t always behave the way you hope, even when you’ve given them a better way to evaluate you.

But the reframing still mattered. It solidified our focus.

We started building for what customers actually needed during bear markets. We launched a savings account that let people keep money with us without exposing it to market volatility. Money doesn’t disappear in downturns — it just moves. In 2022, money market funds saw record inflows as investors fled equities for safety. The money was looking for a home. We gave customers somewhere to go.

Today, over 20% of Betterment’s assets, more than $14 billion, sit in cash products. The scorecard we seeded for customers ended up shaping our roadmap. We stopped measuring ourselves solely on deposits and started measuring ourselves on whether we were the right home for someone’s financial life, up market or down.

That’s the unexpected upside: the scorecard you create for others often clarifies what you should be building in the first place.

Seeding the Scorecard

The tactics vary, but the principle doesn’t: you have to plant the seed early, before people start grading. And the scorecard has to be real. If it’s not auditable, if others can’t verify the work, it’s not a scorecard. It’s spin.

Six months before a big launch, a critical milestone, or a moment of evaluation, share your goals broadly with key partners. Be specific about what you’re optimizing for. Ask them to keep you honest.

Because here’s what most people forget: you can fail a hundred tests you never defined as yours. The metrics exist whether you name them or not. Winter always comes. The only question is whether you’ve seeded the scorecard before it arrives.

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

Join my referral program and earn 1:1 coaching sessions by sharing Frank Takeaways with others - start with just three referrals.
—

The yellow school bus pulled up to the farm at 11:23 AM. I know because I’d been checking my watch. My daughter’s first field trip, and the bus was running late — over an hour behind schedule. We’d have just enough time before loading back up.

A little over an hour later, as we loaded back onto the bus, I asked her what her favorite part was so far.

“The bus ride!” she said, bouncing as we walked back.

Not the chickens, pigs, or goats she’d fed. The bus. The same yellow bus that smelled faintly of diesel and had seats that bounced too hard over every bump.

I started to feel that familiar parental impulse to redirect her attention. “But what about the—” Then I stopped. She’d had a great time. The fact that it wasn’t what I’d planned didn’t make it less real.

I was still thinking about that bus ride when my afternoon coaching call started.

Halfway through the session, a senior executive leaned back and shared something that made me sit up.

“We started talking about whether we should enter China,” he said. “And you know how many times we’ve had that conversation? Too many to count.” He paused. “But it was the first time they’d entertained that conversation. The new folks on the leadership team.”

I waited.

“I used to jump in,” he continued. “Now I sit back. They’re smart. They’ll get there.”

Sometimes when leaders hear “What’s our strategy?“ they panic, thinking it signals confusion or disconnect. But here was the flip side: sometimes the question isn’t a signal at all. Sometimes it’s just the natural conversation that happens when new people join and need to build their own conviction.

The executive had learned to tell the difference. And more importantly, he’d learned that even when it’s the latter, even when it’s just people working through something he’s already worked through, his job isn’t to fast-forward to the ending.

My daughter didn’t need me to curate the perfect farm experience. His new leaders didn’t need him to shortcut the China debate. The hardest part wasn’t deciding whether to help. It was enduring the time it takes for someone else to arrive at something you already know.

The Tax of Seeing Patterns

A strange curse of experience: the better you get at your job, the faster you see patterns. You know exactly where it’s heading. You can predict the objections, the pivots, the eventual landing point.

The impulse feels generous: you’re trying to save everyone time. But you’re actually depriving them of the very experience that made you wise enough to see the pattern in the first place.

What makes this particularly hard isn’t the decision to stay quiet — it’s the duration of staying quiet. It’s not one conversation. It’s three meetings. It’s watching the same ground get covered, again and again, while you sit there knowing the destination.

That’s the real tax: not the moment you bite your tongue, but the weeks and months of watching someone take a scenic route you’ve already driven.

Why This Works: Natural Consequences

Psychologists call this “natural consequences” — the idea that people learn best when they experience the outcome of their choices directly, without someone swooping in to narrate the ending.

A natural consequence is what happens because of an action, not what someone imposes in response to it. Getting hungry after skipping lunch. Feeling cold without a coat. Learning that a market entry strategy needs more research after spending three meetings exploring the angles.

In leadership, natural consequences look like letting your team have the China conversation. Again. Even though you’ve already had it. Even though you know where it’s going. The consequence — whether it’s building conviction, discovering a gap in their thinking, or realizing they need more data — teaches the lesson better than your explanation ever could.

Of course, this only works when you’re not handing them the keys to the rocket — just the steering wheel for a practice run. The China conversation? No decision being made yet, just thinking out loud. Safe environments where natural consequences can teach without causing real damage.

The Discipline of Your Timeline vs. Theirs

When that impulse hits to jump in, I’ve learned to pause and get honest with myself.

Usually, I’m not impatient about the outcome at all. I’m impatient about the process. I’m bored. I’ve seen this movie. I’m ready for the next scene, but they’re still on the opening credits. That boredom is the signal: I’m optimizing for my timeline, not theirs.

The executive who told me about the China conversation had learned something crucial: the conversation wasn’t costing him anything except time. No catastrophic decisions were being made. No irreversible damage. Just... time. And time spent building conviction is rarely wasted.

He’d learned to physically step back — literally walk away to refill his coffee — when the urge to narrate the ending grew too strong. The physical distance helped him resist the urge to impose his timeline on their discovery.

I’ve started treating these moments differently too. Instead of asking “Should I help them?” I ask “Whose timeline am I trying to optimize?”

If the answer is mine — because I’m bored, because I’ve heard this before, because I’m ready to move on—that’s a sign to stay quiet.

How Shortcuts Create Dependency

There’s a particular kind of impatience that comes with experience: you’re not worried they’ll fail, you’re annoyed they’re taking so long to succeed.

Years ago, I worked with a talented PM who proposed a feature direction I had strong opinions about. Every cell in my body wanted to tell her what I knew. Instead, I asked questions. “Walk me through your thinking.” “How will you validate this?” “What would make you pull the plug?”

Three months later, she came back. The approach had moderate traction but not enough to justify continued investment. She’d run the experiment, gathered the data, made the call to sunset it.

Here’s the thing: if I’d jumped in, I’d have robbed her of more than just that learning. I’d have taught her to wait for me to tell her what to do. And dependency is always slower than patience. A team that waits for your answers can only move as fast as your availability. A team that builds its own judgment moves at the speed of conviction.

That PM went on to lead some of our most successful product launches — not because she never made questionable bets again, but because she’d learned to trust her judgment and course-correct quickly. The time I spent watching her work through something I already understood became the foundation for her working independently on things I couldn’t predict.

The Compounding Return on Patience

When you let someone experience something you’ve already experienced, you’re giving them something far more valuable than your advice: you’re giving them their own story.

You’re saying: “I trust your judgment. I believe you can figure this out. And when you do, it’ll be yours, not mine.”

That ownership compounds. They stopped waiting for him to weigh in on every decision. They’d learned to think like owners because he’d let them own the thinking.

This is how you scale leadership. Not by being the smartest person in the room, but by creating more smart people in more rooms. And the only way to create smart people is to let them have the experiences that make them smart — even if you’ve already had those experiences yourself.

The time you spend watching them discover something you already know isn’t wasted. It’s an investment. Every conversation you don’t shortcut builds their capacity to have harder conversations later. Every pattern they recognize for themselves becomes a pattern they can teach someone else.

The Gift You’re Actually Giving

The bus pulled away from the farm, and my daughter pressed her face against the window, waving at the pumpkins we were leaving behind.

I’d ridden a school bus hundreds of times. The magic had long since worn off for me. The diesel smell, the squeaky seats, the bumpy ride — all painfully familiar.

That night at dinner, she was still talking about the bus, breathless and animated, recounting every bump and turn. I realized: my familiarity doesn’t diminish her discovery. My boredom with the ride doesn’t make her joy less real.

Your new leaders will have the China conversation again. Your team will debate strategies you’ve already debated. They’ll encounter challenges you’ve already solved, discover insights you’ve already discovered.

Let them.

Not because you don’t know the answer. Not because you don’t care about efficiency. But because no matter how many times you’ve taken the ride, it’s still someone else’s first time.

The hardest part of leadership isn’t deciding whether to intervene. It’s enduring the time between when you see the answer and when they arrive at it themselves. It’s sitting in your boredom while they sit in their discovery.

They’re smart. They’ll get there. And when they do, they won’t need to ask you if they got it right.

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

Join my referral program and earn 1:1 coaching sessions by sharing Frank Takeaways with others - start with just three referrals.
—

I had the dream again last night. I’m standing in front of a panel of three people with notepads. The lighting is fluorescent and unforgiving. They’re asking me questions about a project I shipped six months ago, and I’m answering them, one by one, trying to prove I thought it through. Why did you prioritize that feature? What about this edge case? Did you consider the alternative approach? My answers sound reasonable in my head, but when they come out of my mouth, they feel thin. I can see it in their faces — I’m not convincing them. I wake up with my heart racing, sheets twisted, that familiar tightness in my chest.

Here’s the thing: I’ve never defended an academic thesis. I don’t have a PhD. I’ve never stood in front of a dissertation committee. But I know that room. I’ve been in a version of it dozens of times — performance reviews, design critiques, postmortems on projects that didn’t land the way we hoped. And I show up the same way every time: shoulders tight, ready to defend. Ready to prove I knew what I was talking about, that I made the right calls, that I’m good at this.

But here’s what I understand now: workplace feedback isn’t a defense. It’s not proof you thought hard enough or chose the “right” path. It’s simpler — and scarier: a readout of impact. How your behavior landed on someone else. That’s it. You don’t have to defend it or agree with it. You decide what, if anything, to do next.

The way out isn’t to accept all feedback or reject all feedback. It’s to stop defending and start choosing.

What We’re Really Protecting

A client I coach — let’s call her Collette — recently told me about a product review that shook her. She’s a talented product leader, and she’d been presenting her roadmap for the next quarter. The feedback was gentle but direct: “This feels like a lot of competing priorities. I’m not sure what we’re actually committing to.” Instead of asking what specifically felt unclear, Collette spent fifteen minutes walking through her research, her stakeholder conversations, her trade-off analysis. She explained decisions twice, added context no one asked for, and ended, a little breathless: “So that’s why I prioritized it this way.”

When she described what happened next — the quiet room, the awkward glances — she said, “I know I did it again. I know I went into defense mode. But in the moment, I couldn’t stop myself.”

I see this constantly in my coaching practice. When someone tells you your behavior had an impact, something primal kicks in. Your throat constricts. Your jaw clenches. You feel exposed, like you’re standing in that fluorescent-lit room again. The feedback triggers an old wound — the fear that maybe you’re not as competent as you appear, that maybe you’re about to be found out.

So you protect what feels most vulnerable: your image as someone who knows what they’re doing. You explain your reasoning because if the reasoning is sound, then you can’t be wrong. If you can’t be wrong, then you’re safe.

Collette wasn’t protecting her roadmap. She was protecting her identity as a careful thinker. This is the core confusion: we treat feedback about impact as judgment about our reasoning. Someone says “this confused me,” and we hear “you’re bad at explaining things.” Someone says “this felt harsh,” and we hear “you’re not a good manager.” But that’s not what they’re saying at all. They’re giving you data about what happened when your behavior met their experience.

What I’ve learned from coaching is that the most defensive responses come from people who are actually quite good at their jobs. It’s not incompetence that makes us defensive — it’s the gap between how hard we’re trying and how we’re landing.

I’ve seen talented leaders plateau because they couldn’t move past this. They stopped getting honest feedback. Their teams learned to manage up instead of speaking up. They lost access to the information they needed most to grow. The defense that was supposed to protect their reputation ended up limiting their impact.

The vulnerability in receiving feedback is real. It means sitting with the possibility that your impact doesn’t match your intent. It means accepting that someone else’s experience is valid even if it doesn’t align with your reasoning. It means acknowledging that competence isn’t just about making good decisions — it’s about creating good outcomes.

But here’s what’s paradoxical: the more you defend against this vulnerability, the more vulnerable you actually become. Because everyone can see the defense. Everyone can feel the resistance. And resistance doesn’t inspire confidence — it erodes it.

The Power of Choice

Once you stop defending, something remarkable happens: you realize you have options. Real options. Not the false choice between “accept all feedback” and “defend everything,” but actual strategic choices about how to respond.

Option 1: “That’s useful information. I want to change that.” This is the response when the feedback aligns with your values and goals. You’re not admitting failure — you’re acknowledging impact and choosing to adjust. “I hear that my direct communication style is coming across as dismissive. I don’t want people to feel dismissed, so I’m going to work on that.”

Option 2: “I hear that it landed that way. I’m going to keep doing it anyway because [reasons].” This is the response when you understand the impact but decide the trade-offs are worth it. “I know my focus on deadlines creates some pressure, but given our current situation, I think that’s the right trade-off for now.” You’re not dismissing their experience — you’re making a conscious choice based on competing priorities.

Option 3: “I need to understand more. Can you help me see what you saw?” This is the response when you want to learn more before deciding. “You mentioned that the meeting felt chaotic. Can you walk me through what specifically felt disorganized? I want to understand what you experienced so I can figure out what to do about it.”

Option 4: “I hear you, and I’m noticing we see this differently.” Sometimes feedback reveals more about the feedback-giver than about you. Maybe they’re under unusual stress, maybe they have a blind spot, maybe they’re not the right person to evaluate this particular area. That’s still useful information. You can acknowledge their experience without changing your behavior: “I hear that landed differently for you than it did for others. That’s helpful context.”

None of these require you to be wrong. They just require you to take the information seriously. They acknowledge that impact matters, even when intent was good. They demonstrate the kind of leadership maturity that actually builds trust: the ability to hear hard things without getting defensive.

Choosing beats defending. It shifts you from needing to be right to needing to be effective. It moves the conversation from your reasoning to their experience. It makes the feedback about the work, not about your worth.

How to Actually Do This

When you feel the defense rising, name it — even just to yourself. “I’m feeling defensive right now. That’s interesting.” Naming the emotion creates space between you and the reaction. It gives you a moment to choose your response rather than just reacting.

Try this phrase: “Let me make sure I understand what you experienced.” Say it before explaining anything. Before adding context. Before sharing your reasoning. Just make sure you understand their experience first. This does two things: it shows you’re taking their feedback seriously, and it gives you information about what actually happened from their perspective.

Remember that impact and intent are different things. Intent is your aim; impact is their experience. You can honor someone’s experience without agreeing that your intent was wrong. “I didn’t intend for that to feel dismissive, and I understand that it did. That helps me see how I can be more effective.”

Sometimes feedback is poorly delivered, feels unfair, or misses the mark. You still don’t have to defend — but you may need to clarify. That’s the line between defensive and discerning. Defensive sounds like: “That’s not true because...” Discerning sounds like: “Help me understand how you see this differently because...”

If a comment crosses a line, set a boundary: “I’m open to feedback on the work. I’m not okay with personal remarks.”

Practice the phrase “I want to think about that.” It’s your get-out-of-jail-free card for avoiding real-time defensiveness. You don’t have to have a response immediately. You don’t have to fix everything in the moment. You just have to demonstrate that you’re taking it seriously.

The long game here is about building trust. People need to believe you can hear hard things without falling apart or getting combative. They need to see that feedback makes you more effective, not more fragile. That’s how you become the kind of leader people are willing to be honest with — which is the only kind of leader who can actually improve.

Learning to Choose

I still have the dream sometimes. The fluorescent room, the panel, the questions I can’t quite answer well enough. I don’t think it’s going away.

But I’m learning to recognize that feeling in real life — that heat rising in my face, that urge to explain everything. And more often now, I can choose something different.

That’s what becomes possible when you stop defending and start choosing.

The room doesn’t disappear — you just realize you’re not trapped in it.
The questions don’t stop coming — you just stop treating them like attacks.
The feedback doesn’t get easier — you just get better at receiving it.

The best leaders I know aren’t the ones who are never wrong. They’re the ones who can hear they’ve had an impact and decide what to do about it. They understand that effectiveness isn’t about perfect reasoning — it’s about consistent results and reliable relationships. They know that feedback isn’t a judgment on their competence — it’s information they can use to get better.

The defense is over. The choice is yours.

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

Join my referral program and earn 1:1 coaching sessions by sharing Frank Takeaways with others - start with just three referrals.
—

The woman on stage was talking about hermit crabs when I heard something that made me sit up:

"I would actually agitate them more. Today I'm the ocean, and today the ocean is dirty and mean!"

I'd never have been at this Pop-Up Magazine show if my former manager hadn't insisted. I was half-listening to Mary Akers explain how she'd accidentally become the world's most successful hermit crab breeder when that word — agitate — hit me like a wave.

That's when I understood what I'd been doing wrong as a leader for years.

After writing about where to position yourself (The Proximity Trap) and why to persist (The Good Stuff), readers kept asking: "But what do I actually DO when I get there?"

Mary had just given me the answer to a question I didn't even know I was asking.

There’s Something About Mary

She never meant to become a hermit crab breeder. She was an empty nester, pet-sitting for a friend, and ended up with a tankful of hermit crabs — each one stolen from a beach from halfway around the world, given a crabitat with a fluorescent gravel future.

When Mary realized these "throwaway" pets could actually live for decades — if cared for well — she decided to take responsibility. She built them a habitat the size of a grand piano and decided to tackle what no scientist had solved: breeding hermit crabs in captivity.

Her first attempts? Disasters. Mary hovered anxiously, adjusting water temperature by the degree, swapping foods at the first sign of distress. When her baby crabs died, she obsessed over what she wasn’t providing. More warmth? More food? More intervention?

But more wasn’t the answer. She was giving them performative care — the kind that soothes the caregiver, not the creature. What the crabs actually needed was something closer to the ocean itself: unpredictable, sometimes rough, always generative.

Mary couldn’t be God. She had to be the ocean.

Caring Isn’t About Comfort

Mary's discovery wasn't about crabs. It was about the gap between performative care and generative care — a gap I see in every leadership interaction.

In a recent coaching session, a VP was spiraling about her performance review with a struggling designer. "I've rewritten this feedback six times," she said. "I need to find exactly the right words so it lands perfectly. So they feel supported while understanding they need to grow."

I could hear that familiar tightness — the knot in your chest when you're trying to control an outcome while pretending you're just having a conversation.

"What if you didn't have to be perfect?" I asked. "What if you just had to create the right conditions?"

We've got it backwards. We think leadership means eliminating every bump, crafting every message so precisely that growth happens without discomfort. We perform care by hovering, adjusting, preventing pain.

But that's not how oceans work.

When Mary finally succeeded — when 204 baby crabs climbed from water to land in her makeshift ocean — it wasn't because she'd eliminated struggle. It was because she'd learned to create productive turbulence.

"I would actually agitate them more," she said, "move it around and give them, like, a low tide and a high tide."

That word — agitate — stops me every time. We spend so much energy trying to calm waters, and here's Mary deliberately churning them up.

The ocean doesn't apologize for its waves.

Molting Season: When Growth Means Shedding Our Shell

Like hermit crabs that must leave their shells to grow, I know what it feels like to be vulnerable in someone else's carefully constructed environment.

Years ago, my coach watched me spin for twenty minutes about a team conflict I couldn't resolve. I'd tried everything: one-on-ones, team exercises, process changes. Nothing worked, and I was exhausted from managing everyone's feelings about it.

Finally, she said: "What if this conflict is exactly what your team needs right now?"

I wanted her to give me a solution. Instead, she gave me a question that made my chest tight: "What are you afraid will happen if you stop trying to fix this?"

The answer came immediately: "They'll think I'm a bad manager."

"And then what?"

"They'll lose respect for me."

"And then?"

"I'll lose my job."

She let me sit in that discomfort. Didn't rush to reassure me or offer strategies. Just waited while I felt the full weight of trying to control something I couldn't control.

"What if," she said quietly, "your job isn't to eliminate their conflict, but to create conditions where conflict becomes productive?"

That conversation changed everything. Not because she solved my problem, but because she let me struggle with it in her presence. She was my ocean.

How to Be the Ocean: Creating Your Own Currents

Just as Mary learned to simulate tides and create productive turbulence, here's how to bring ocean-like leadership to your daily practice:

The Generosity of Early Honesty

One of my clients was tying himself in knots trying to explain why someone wasn't ready for promotion. I told him: "Close the door. Say she's not ready. If your boss wants to reopen it, she will."

The ocean doesn't hedge. The tide comes in.

A month before reviews, start the conversation. "You're phenomenal at visual design. I think you'd grow your influence if you could create the narrative around your concepts. What do you think?" Let them sit with that. Let them feel the pull of the current before the wave arrives.

This isn't cruel. It's honest. And honesty, delivered early, is generous.

Rhythms, Not Rescues

At Google, we wrote weekly "snippets": short notes on what we'd accomplished and what was next. Like the predictable rhythm of tides, these regular check-ins created a pattern of accountability. The discipline was uncomfortable, but the consistency helped us develop stronger habits — much like how Mary's crabs adapted to the rhythmic patterns of her artificial ocean.

That's ocean behavior: creating rhythmic patterns that shape growth through persistent, predictable challenge.

When I worked at a startup where the founder kept doing design drive-bys, I didn't try to stop him. I created a weekly design review forum. Same feedback, different container. Predictable tides instead of rogue waves.

The ocean doesn't eliminate chaos. It makes chaos productive.

Let Them Struggle (But Not Drown)

This is the hardest part. The part that costs something.

When you watch someone defensive about their work, every instinct screams to jump in. To soften the edges. To make it easier. Your throat tightens. Your hands want to move. You feel the urge to save them from the discomfort you've created.

Don't.

Mary put it perfectly: "Life for me, my lesson has always been just let go, Mary. Let them be crabs."

Your job isn't to eliminate their discomfort. Your job is to create conditions where discomfort leads to growth.

"You're phenomenal at visual design," you might say. "But you can't create the narrative around your concepts. How is that limiting your impact?" Then — and this is key — you let them sit in that discomfort. You agitate the water and wait.

Sometimes dirty, sometimes mean, always in service of growth.

But here's what nobody tells you about becoming the ocean: it changes your relationships.

When you stop performing care, some people feel abandoned. The ones who depended on your hovering, your endless adjustments, your willingness to absorb their discomfort — they'll push back. They'll tell you you've gotten "cold" or "demanding."

You haven't. You've just stopped being their anxiety management system.

People who've grown comfortable with your performative care will resist your generative care. They want you to keep managing their feelings instead of creating conditions for their growth.

The ocean doesn't personalize resistance. It just keeps being the ocean.

Tides and Time

Three months later, the VP texted: "Remember that designer? She came back with a plan. She's owning her development now."

That's what generative care creates.

But it requires getting comfortable with discomfort. Sitting with the physical sensation of watching someone struggle with feedback you could soften. Feeling your chest tighten when they push back and resisting the urge to explain yourself into oblivion.

When the urge to intervene grew too strong, Mary would whisper to herself: "Today I'm the ocean, and sometimes the ocean is dirty and mean." Not cruel, not capricious, but true to its nature — creating the conditions where life finds its own way to thrive.

By the end, Mary was breeding 700 crabs a year. She'd solved what trained scientists couldn't. Not through expertise, but through understanding something fundamental:

Love means letting go of control while maintaining conditions for life.

The hermit crabs that survived Mary's artificial ocean weren't the ones she saved. They were the ones who learned to save themselves in the environment she created.

That's the job. Not to eliminate struggle, but to make it generative. Not to prevent every wave, but to create the conditions where waves lead to growth.

Not to be God. Just to be the ocean.

—

Hear Mary tell it herself in Radiolab's Crabs All The Way Down.

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

Join my referral program and earn 1:1 coaching sessions by sharing Frank Takeaways with others - start with just three referrals.
—

My sister and I would pass them around the backseat like sacred scrolls. Those spiral-bound AAA TripTiks, with their narrow strips of highlighted highway and hand-circled rest stops. This was 1990s, and we were driving from Maryland to Disney World. No GPS. No smartphones. Just these custom-made guidebooks that showed you one thing: how to get from here to there, with just enough detail to make the journey interesting.

The binding cracked when you folded back each page. In the margins, the AAA agent had written cryptic notes in blue ballpoint: "Good BBQ here" or "Clean restrooms" or "Skip - tourist trap." Each page revealed maybe 50 miles of road. You couldn't jump ahead to see the whole route. You had to trust the process.

I've been thinking about those TripTiks lately, especially during planning season — when product teams lock in multi-month roadmaps, professionals chart career plans, and everyone asks AI to optimize their path forward. We've all fallen for the same delusion: that we can algorithmically plan our way. Now we're doubling down, asking machines to be even more precise about predictions that were already fiction.

The TripTik understood something we've forgotten. The best journeys — products or careers — aren't about perfect navigation. They're about having just enough structure to move forward confidently while staying flexible enough to discover something better along the way.

When Perfect Plans Make You Sick

Here's what nobody talks about during planning season: that tension in your shoulders when the board asks about Q4 deliverables in January. The knot in your stomach when you're asked for your five-year career plan.

Your body knows what your spreadsheet won't admit: you're lying to yourself.

A little anxiety sharpens focus — remember taking the AP Calculus exam? But constant anxiety about controlling the uncontrollable creates paralysis. You spend so much energy maintaining the fiction of certainty that you have none left for the actual journey.

My friend Sarah learned this the hard way. Stanford CS degree, Google APM program, fast-track promotions. By 32, she was Head of Product at a unicorn startup, exactly where her life plan said she'd be.

I met her for coffee last year. She looked exhausted. "I'm in a meeting about optimizing ad revenue," she said, "and I realize I don't care. Not even a little bit. I'm building features for metrics I don't believe in, for users I've never met. But this was supposed to be the dream job." Her Sunday night panic attacks had gotten so bad she'd started taking Mondays off.

The same thing happens with product roadmaps. I've watched teams commit to features in Q1 for Q4 delivery, then spend the next nine months defending decisions that stopped making sense by Q2. They ship what they promised, not what users actually need. The roadmap becomes a prison, not a guide.

The Lost Art of Waypoint Planning

The TripTik's genius was its waypoints. Not a rigid route, but suggestions. A scenic overlook here. A famous diner there. Each page showed just 50 miles — enough to move forward, not so much you couldn't adapt.

Compare that to how we plan now. Career paths become ladder-climbing exercises: Senior PM by 28, Director by 32, VP by 35. Product roadmaps become feature factories: Authentication in Q1, Payments in Q2, Analytics in Q3. We're so focused on destinations we miss the actual journey.

The irony? At our best, we understand this principle with AI tools. You wouldn't ask Claude to 'write me the perfect app' without any context. You'd start with your specific problem, iterate on solutions, and build up complexity gradually. But somehow when it comes to career or product planning, we reach for tools to input our constraints and get back the optimal path. We're asking the wrong questions of ourselves.

Good waypoints are different. They're about capabilities and experiences, not checkpoints:

For careers: "I want to see a product scale from 10 to 10 million users" beats "I want to be a Director." One teaches you something. The other just changes your email signature.

For products: "We need to understand user retention deeply" beats "Ship analytics dashboard." One creates learning. The other creates features that might miss the mark.

The Art of Productive Meandering

Let me tell you about my best career detour. In 2018, I joined Casper — it was a detour from my other roles. To this day, it always registers the most questions from future employers, "Tell me about your decision to join Casper." If you were to put all of the logos from companies I've worked on a sheet of paper and ask someone to circle the one that doesn't belong, 10/10 they'd pick Casper. It's the only D2C company and the only company with a physical product. It's a company where I was sometimes referred to as working in the IT department.

So whenever I'm asked I always give the same response — I look them in the eye deadpanned and say, "Because I wanted to sell mattresses." I try to hold it together for a few seconds before cracking a smile. No, selling mattresses wasn't the my career goal. It was a detour. I wanted to push myself to scale my impact through others — to refine my leadership skills. You know what isn't important to do that? The tech stack. You know what is? Support from your manager, partners, and team to grow, try, fail, rinse, and repeat.

What that detour gave me was depth. I already knew the theory of leadership — create conditions for others to succeed, focus on the team, build people who build products. But knowing something and living it are different. At Casper, with the tech stack out of the way, I could spend all my mental energy on the nuanced work of actually leading.

When I returned to more traditional tech product work, I wasn't just applying leadership principles, I was applying battle-tested instincts I'd developed through focused practice.

Was it optimal for reaching VP? No. Did it make me better at leading others? Absolutely.

The discomfort of not knowing exactly where you'll be isn't a bug — it's a feature. It means you're navigating reality, not a fantasy.

Building Your Own TripTik

Whether you're planning a career or a product roadmap, here's how to think like a TripTik instead of an algorithm:

Start with direction, not destination. "Build products that make work more humane" beats "VP of Product at a public company." "Help small businesses succeed online" beats "Process 1M transactions monthly." Directions flex. Destinations break.

Identify must-see experiences. What would you regret missing? Working at an early-stage startup? Shipping something your mom would use? Building a team from scratch? These are your waypoints. For products: What capabilities must you build? What user problems must you solve? What technical foundations can't be skipped?

Plan in 50-mile chunks. The TripTik showed one segment at a time. Plan the next quarter in detail, the following quarter in themes, everything else in directions. For careers, focus on the next role deeply, the one after that loosely, and let the rest be directional.

Build in rest stops. The TripTik always showed where to pause. Your plans need these too. Regular retrospectives. Time to ask: Are we still headed where we want to go? Is this still the right direction?

Reading the Road Signs

How do you know if you're productively meandering or genuinely lost?

You're on track when:

• You're learning something that changes how you work

• Each experience connects to your larger direction

• The discomfort feels like growth, not drowning

• You can explain why this detour matters

You're lost when:

• You're only there for the title or metrics

• You can't connect current work to larger purpose

• You're executing without learning

• The anxiety feels paralyzing, not energizing

Your Journey, Your Rules

We create rigid plans not because they work better, but because choosing from infinite options feels terrifying. Black and white is simpler than navigating infinite grays. So we build detailed roadmaps, chart exact career paths, and now ask AI to make these fictions even more precise — as if higher resolution could somehow make uncertainty disappear. But that rigidity is what's making you sick, literally. The tension in your shoulders, the Sunday night dread, the defensive roadmap reviews where you justify outdated decisions.

We kept those TripTiks for years in the seat back pocket of our Jeep Cherokee. Sometimes I'd pull them out and trace the route, remembering not just where we went but what we discovered.

Years after that Disney pilgrimage my family moved to Savannah, GA — a city we discovered on the journey.

—
What waypoints guide your planning? How do you balance structure with flexibility? I'd love to hear about the detours that taught you more than any straight path could.

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

Join my referral program and earn 1:1 coaching sessions by sharing Frank Takeaways with others - start with just three referrals.
—

Memorial Day flips the calendar to summer and reminds every product leader that Q2 is already half-gone. Roadmaps are red-lined, OKRs rewritten, and somewhere between backlog-grooming and booking this summer’s Airbnbs you’re wondering how a big bet promised in January will stay fresh until December.

Last Saturday, I was the human pack-mule: bike trailer full of kids, picnic gear over one shoulder, SPF 50 wedged under my chin, and my phone chirping its 10% battery warning. Did I pack the portable charger? A gust of wind sends both kids scattering, leaving me corralling toddlers instead of checking supplies. First stop: the Prospect Park Zoo. Then a picnic on Nellie’s lawn. When I finally collapse onto the blanket, I reach into an un-insulated canvas tote and fish out what should, by all laws of thermodynamics, be a disaster: a sandwich that has stewed for five hours in direct sun.

Instead of the mushy horror we've all unwrapped at least once, it's glorious. Five hours of heat and pressure have somehow elevated it. It tastes better than when I assembled it at dawn. No special handling. Just a piece of design wisdom so thoughtful it shrugs off heat, pressure, and neglect.

That cooler-free beach sandwich? That’s your product benchmark. Life is windier, noisier, and patchier than any usability lab. Real users meet your app mid-commute, mid-crisis, or mid-kid-wrangling with a sandy thumb and half their attention.

Where will your customer first meet the feature you’re shipping this quarter?

A Thousand-Year Lesson in Portability

(Let me have fun with this. It’s been a long week.)

Before we dive into the principles, it’s worth asking why a sandwich can be such a reliable teacher. The term “sandwich” begins as a place — Sondwic, an Anglo-Saxon market town literally built on sandbanks. By the 18th century it passes to the Earl of Sandwich, who demands meat between bread so he can gamble without greasy cards. Legend. Fast-forward two more centuries and the sandwich completes its destiny, returning to literal sand as the essential beach companion.

Enter Hailee Catalano, according to Food52, the internet’s undisputed beach-sandwich authority. Her philosophy hit me like a UX audit: design for the destination, not the photos. She packs crusty bread that absorbs oil without collapsing, layers fillings so thin they compress into a single bite, and refuses a cooler because, in her words, she’s “too excited to wait.”

Hailee’s sandwiches are built to serve the beachgoer’s day — not to steal attention or demand just-in-time logistics. That same intentionality is what separates a product that works in conference-room demos from one that works on a subway platform at 6 p.m. Let’s translate her rules into five design tenets for building sun-proof, journey-proof products.

Tenet 1: Serve the Journey, Don’t Hijack It

A beach sandwich supports your plan; it never asks you to reorganize lunch around an elaborate sauce packet. Likewise, a great product amplifies a user’s goal instead of forcing a detour into the product’s agenda.

• Exemplar: Apple Wallet boarding passes surface gate, zone, and QR code directly on the lock screen. No hunting for the airline app, no email spelunking. The product respects the “sprinting through C-terminal” reality of travel.

• Counter-example: Airline apps that gate your pass behind mandatory surveys or last-minute hotel-up-sell modals. They hijack urgency for internal vanity metrics — akin to a sandwich that makes you assemble toppings at your towel because “presentation.”

Design prompts

• What business metric could you hit without inserting another step?

• If your feature disappeared mid-flow, would users cheer (fewer hoops) or curse (lost progress)?

Field test: Hand your prototype to a colleague rushing to the next meeting. If you see even a single eyebrow-raise, you’re hijacking.

Tenet 2: Design for Hostile Contexts

Beach sandwiches assume hostile variables: heat, glare, sand, uneven pressure. Products must assume the digital equivalents — poor connectivity, loud environments, cognitive overload.

• Exemplar: Google Docs offline mode silently stores edits and reconciles later. It treats a dead spot like a weather event, not a user error. (YouTube automatically adjusting its streaming quality with slow connections is another great example.)

• Counter-example: Pretty much every LLM chat product that doesn’t handle drops in connectivity. It goes from feeling like you have a super power by using AI to being a chump and having to retype everything.

Design prompts

• List the three most likely failure modes (network drop, dead battery, permissions denial). What actually happens when each strikes?

• Does the UI degrade gracefully, or does it toss a modal tantrum?

Field test: Throttle your dev phone to 3G, turn brightness to max, stand outside at noon. If you can’t complete the critical path, the product fails the sand-and-sun test.

Tenet 3: Min-Ask UX

You should be able to eat lunch with one sandy hand. Your customer should achieve value the same way: fast, single-minded, friction-light.

• Exemplar: Slack emoji reactions convey tone in a tap — no compose window, no "Send" button, no cargo-cult thread, or Venmo "Recent payments" guesses the friend you probably owe and surfaces the payment tile up front. It removes the social-graph scavenger hunt associated with splitting pizza.

• Counter-example: Date pickers that reject simple text inputs ("next Tuesday") or rigidly enforce calendar widgets.

Design prompts

• Time a first-time user from launch to “moment of value.” Can they do it in under 15 seconds?

• Which data inputs are truly required? Pare one away and retest.

Field test: Ask a teammate holding a coffee to perform the task with the thumb of their non-dominant hand (or with just the mouse). If they need to set the drink down, your flow demands too much dexterity.

Tenet 4: Portability Across Sessions

Beach days are stop-and-start; so are digital workflows. Assume device switches, time gaps, and context shifts.

• Exemplar: Chrome’s “Continue browsing” restores tabs on any device without administrative ceremony. Or maintaining unread messages across devices.

• Counter-example: Having to repeatedly re-authenticate on different parts of the app or having to sign-in at the end of a task and losing your progress.

Design prompts

• If a user returns tomorrow, can they resume mid-bite or must they rebuild context?

• Where does your backend store in-progress state and for how long?

Field test: Begin a task on laptop, close the lid, finish on mobile 24 hours later. Any re-authentication or missing data is a leak.

Tenet 5: Room-Temp Durability

The best beach sandwiches gain flavor after hours — the olive oil seeps, the herbs bloom. Stellar products age gracefully, too.

• Exemplar: Dropbox version history lets teams recover from mistakes weeks later. Every edit accretes value instead of risk.

• Counter-example: Having to repeatability set your preferences (e.g. shirt or pant size on an ecommerce website) with each session.

Design prompts

• Which part of your product genuinely improves with each additional use?

• Where do you unintentionally rot user data (unmigrated schema, lost drafts, expiring links)?

Field test: Leave an account idle for a month, then log back in on a new device. Does orientation feel like picking up a marinated sandwich or a wilted salad?

Scorecard

The Desktop Delusion

Here's the dangerous assumption: "Our users are at their desks with good wifi." Even enterprise software teams fall into this trap, designing for the happy path of perfect conditions. But enterprise software can have high-frequency use and tiny frictions compound into chronic pain.

I've watched teams build desktop experiences that fall apart the moment someone tries to demo on their phone, or review a doc while commuting. Ironically, your stakeholders — the decision-makers reviewing your progress — are most likely to encounter your product precisely in these unpredictable contexts.

The warning signs you're optimizing for the lab instead of the journey:

• Your team demos exclusively on large monitors with perfect connectivity

• User research happens in conference rooms, never coffee shops or commuter trains

• Your analytics show high abandonment rates on mobile, but you blame "mobile users don't convert"

• Features work beautifully until someone switches devices mid-task

If your users live in the real world (Narrator’s voice: they do), pack the sandwich principles.

The Sandwich, the Circle, the Lesson

You might not have recognized the "beach sandwich" by name — it's never listed next to club sandwiches or Reubens — but you’ve definitely experienced its soggy, sand-flecked nemesis at least once.

The best product mentor you'll meet this summer won't be in your Slack messages or at your next offsite. Instead, it's wrapped and slightly dented in your bag — a humble sandwich that's completed a surprising thousand-year journey to reach your picnic blanket.

Last weekend, my sandwich passed the Hailee Catalano test: crusty Italian bread, muenster cheese, roasted turkey, a thin butter barrier (moisture management, naturally), and a brine-y pesto up-cycled with capers and sun-dried tomatoes.

It embodied every principle above: support, resilience, minimal demand, flawless hand-off (from tote to mouth), and flavor that intensified over time. That’s the same bar I’m setting for the features slated in my own Q3 roadmap.

Before you sign off on yours, ask one ruthless question: Will this feature survive heat, glare, and gaps in attention? Or will it melt faster than mayo at noon?

Design for the real journey — no safety nets — and the lab demo will take care of itself.

—
Have a topic you'd like me to explore? Drop me a line and your idea could be featured in an upcoming newsletter.

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

Join my referral program and earn 1:1 coaching sessions by sharing Frank Takeaways with others - start with just three referrals.
—

You're at an izakaya restaurant in Manhattan, staring down at the overly complicated tablet ordering system. Dozens of dishes, countless modifications, nested menus that lead to more menus. You're hungry, overwhelmed, and increasingly annoyed. You just want dinner, not a design puzzle.

When you finally need help, you discover that even requesting human assistance requires navigating to a sub-menu where you literally add "server" to your cart and select quantity. "Just give me the next step," you mutter, before flagging down an actual human, relieved to bypass the digital absurdity.

That night stuck with you because it mirrored something you've seen countless managers get wrong: They flood their teams with the whole "menu" — the entire strategic vision, every possible initiative, mountains of context — when all people really need is clarity on what to do next. The irony? These managers think they're being transparent and thorough. They're actually creating paralysis.

The Big Idea

Progressive disclosure isn't just for elegant user experience; it's essential for leadership. Great managers don't bury teams under the weight of every possibility. They carefully reveal information, just enough and just in time, to keep people focused, confident, and moving forward. It's not about withholding; it's about curating. Because when everything feels urgent, nothing actually is.

Think of it as the difference between handing someone a GPS versus throwing them a globe. Both contain the information they need. Only one helps them get where they're going.

It's recognizing a fundamental truth about leadership — your primary job isn't providing all the answers. It's creating momentum and clarity through constraint. The best leaders are editors, not encyclopedias.

Complexity is Costly

We've all been there: the all-hands meeting where leadership shares the "complete vision" with forty-seven strategic pillars, endless OKRs, competing priorities that somehow all matter equally. People nod along, scribbling notes they'll never revisit. Two weeks later, when you check in on progress, you get blank stares and busy work. The team isn't lazy or confused — they're cognitively overloaded.

Consider the genius of transit maps. Harry Beck's 1931 London Underground design revolutionized navigation by showing only what matters — connections and sequence. Not geographic accuracy, not street-level detail, not the curvature of every tunnel. Just enough to get you from here to there.

This principle proved so powerful that NYC just embraced it again — their new 2025 subway map deliberately sacrifices geographic precision for clarity, reviving elements of Massimo Vignelli's controversial 1972 design. Back then, New Yorkers rejected Vignelli's abstract approach and demanded "accurate" maps that showed every curve of track. Fifty years later, we've learned that accuracy isn't clarity. The new map strips away geographic fidelity to highlight what actually matters: how to get where you're going.

That's progressive disclosure at its finest — complexity stripped to its functional essence. Sometimes you have to wait decades for people to realize that more information isn't better information.

The research backs this up. Miller's Law tells us humans can hold roughly seven items in working memory. Sweller's Cognitive Load Theory goes further, showing how excessive information actively impairs learning and decision-making. When managers dump everything at once, they're not empowering teams — they're ensuring nothing sticks.

I know what you're thinking: "But I believe in transparent leadership!" So do I. The difference is recognizing that transparency and clarity aren't the same thing.

I learned this the hard way. Fresh into management, I'd share everything with my team: board deck insights, long-term roadmaps, every executive concern. I thought radical transparency meant total transparency. Instead, I created a team that spent more time worrying about hypothetical futures than shipping actual features. One engineer finally pulled me aside: "Frank, I just need to know what to build this sprint."

That's when it hit me: Clarity isn't about perfect information — it's about perfect focus.

The Power of Progressive Disclosure

In design, progressive disclosure means revealing complexity gradually — showing basic functions first, advanced options later. Gmail doesn't explain filters before you've sent your first email. Good design respects the user's journey.

Good management works the same way. It's about aligning visibility with readiness, matching information to capacity. Not because your team can't handle complexity, but because they shouldn't have to juggle what isn't relevant yet. You'll juggle all this complexity so your team doesn't have to. That's the job.

At Slack, I watched our most effective engineering manager run sprints like a master chef runs a kitchen. Monday stand-ups focused solely on the week ahead. No mention of next quarter's reorg, no discussion of the competitive landscape. Just: here's what we're shipping, here's why it matters, here's who owns what. Strategic context came in monthly one-on-ones, tailored to each person's role and growth trajectory. Roadmap changes were shared in digestible phases, timed to when teams could act and reflect.

The result? Her team shipped more, stressed less, and stayed more engaged than any other. They weren't sheltered from complexity but protected from premature complexity.

But here's the nuance: This isn't about keeping secrets or playing power games with information. It's about recognizing that trust is built through reliability, not data dumps. When you consistently share what matters when it matters, teams trust you more, not less. They know you're filtering for signal, not hiding the noise.

With senior team members, progressive disclosure looks different. They need strategic context earlier, the "why" behind the "what," just not every possible "why" all at once. A staff engineer needs to understand architectural decisions that might land in six months. A junior engineer needs to understand this sprint's technical approach. Both get what they need to be successful, neither gets overwhelmed with irrelevance.

The single difference between the most junior to most senior level in every job function is their ability to handle ambiguity. Your audience matters.

So how do you actually do this? How do you move from theory to practice without becoming the very information gatekeeper you're trying not to be? The key is having clear principles for what to share when and sticking to them even when it feels easier to just dump everything on the table.

Making Progressive Disclosure Practical

Here's a simple framework for deciding what to share when:

• Share NOW: What changes someone's work this week

• Share SOON: What changes their work this quarter

• Share LATER: What changes their role or career trajectory

And here are three techniques you can implement immediately:

1. "Now, Next, Later" Roadmaps Instead of showing the entire product roadmap, break it into three horizons. "Now" gets full detail — specs, dependencies, success metrics. "Next" gets rough scope and rationale. "Later" is just thematic direction. Update the buckets monthly, promoting items forward as they become relevant. Your team stays oriented without drowning in details that might change anyway.

It's important to do all three because sometimes the team won't be excited about the NOW (building internal tools to help other parts of the business) and more excited about the LATER (innovation that drives the long-term mission). By ignoring the LATER, you miss an opportunity to inspire them and keep them invested.

2. Just-in-Time Coaching Stop front-loading feedback. That annual review with seventeen development areas? Useless. Instead, deliver micro-feedback moments before it's needed. About to run their first design review? That's when you share facilitation tips. Leading a contentious stakeholder meeting? Quick prep on conflict navigation. Learning sticks when it's immediately applicable.

3. Staged Onboarding Paths New team members don't need to understand your entire tech stack on day one. Create learning paths that reveal complexity progressively. Week one: ship a small fix using basic tools. Week two: understand the service they're working on. Month two: explore adjacent systems. By month six: architectural decisions. Each stage builds on the last, creating confidence instead of overwhelm.

How do you know if you're getting it wrong?

Signs of under-sharing:

• Repeated questions about the same topics

• Surprise when changes land

• Work that misses the mark on intent

• Team members inventing their own context

Signs of over-sharing:

• Analysis paralysis in team meetings

• Low output despite high activity

• Existential anxiety about future changes

• Focus on tomorrow's problems over today's work

What about when they ask for more?

Sometimes team members will ask for information you haven't shared yet. Resist the urge to open the floodgates. Instead, probe: "What specific concern is driving this question?" Often, they don't need the whole answer — just reassurance about one particular angle. Give them the piece that addresses their actual worry, not the entire puzzle.

The Clarity Covenant

You return to that izakaya dinner, now seeing it differently. The best restaurants don't hand you an encyclopedia of every possible dish — they offer a thoughtfully curated menu. A great server reads the table, suggests what pairs well, knows when you're ready for the next course. They create an experience by revealing options progressively, matching the meal to your mood and appetite.

As managers, we make an implicit covenant with our teams: In exchange for their focus and effort, we'll provide clarity and direction. Not perfect information but perfect focus. Not every possible detail — exactly the right details at the right time.

This is harder than radical transparency. Anyone can forward every email, share every doc, invite everyone to every meeting. It takes judgment, empathy, and constant calibration to reveal complexity progressively. To know when someone's ready for more context. To resist the urge to overwhelm in the name of openness.

But when you get it right, something magical happens. Teams move faster because they're not paralyzed by possibilities. They make better decisions because they're focused on relevant constraints. They trust you more because you consistently deliver what they need to succeed — no more, no less.

Your job as a leader isn't to flood your team with information. It's to be their filter, their guide, their clarity creator. To ensure they always know the next right step without losing sight of the destination. To practice progressive disclosure not as a tactic, but as an act of respect for their cognitive bandwidth and current capacity.

After all, whether you're designing interfaces or leading teams, the principle remains: Don't show them everything at once. Show them what matters now. Because the best managers aren't encyclopedias — they're editors. And the best teams aren't informed about everything — they're clear on what matters.

That's what great management and great meals are all about.

—
Have a topic you'd like me to explore? Drop me a line and your idea could be featured in an upcoming newsletter.

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

Join my referral program and earn 1:1 coaching sessions by sharing Frank Takeaways with others - start with just three referrals.
—

Among product circles — especially the self-anointed Twitter/X PM Elites — there's a quiet hierarchy: "pure" PMs, guardians of taste and user empathy, look down on those who get close to Sales, rolling their eyes at "feature factories" and "customer requests." To them, working with Sales means compromising vision — building what sells rather than what's "right."

This isn't just arrogant; it's lazy. Because craft without adoption isn't craft — it's just theory. Ignoring feedback from Sales doesn't protect quality — it avoids the messy reality of shipping products people genuinely want. When I was designer at Google we used to say "real designers ship" — and the same goes for PMs. Your work isn't done until users and buyers embrace what you've built.

Pretending you're above Sales isn't discipline, it's malpractice.

Sales is Bruno from Encanto — the misunderstood uncle hiding in walls whose visions everyone secretly needs but publicly dismisses. With AI democratizing product development, "good enough" products are cheaper and faster to build than ever. When everyone can ship decent products, your distribution becomes your moat.

I've been that PM, nodding politely in sales meetings while dismissing anything flagged as "a customer request." I told myself it was about integrity; it was really about comfort and control.

I was wrong.

When I was at Slack, we overhauled our Developer Platform. It's challenging to launch a complex, technical ecosystem — complete with APIs, infrastructure, and developer tooling — and even harder to clearly communicate the value externally. I underestimated how critical it was to involve GTM teams earlier to help Sales deeply understand and confidently pitch the platform vision. As a result, we launched without strong sales alignment, had to scramble to build internal clarity post-launch, and adoption suffered.

If you aren't actively building deep partnerships with GTM teams, you're limiting your impact. The productive tension partnership creates consistently outperforms avoidance.

Our Trauma Is Showing: "Taste" as an Excuse

We all know the stereotypes:

• Sales: Short-term wins, impulsive feature requests.

• Product: Ivory-tower visionaries, detached from commercial realities.

We blame misaligned incentives — Sales' quarterly quotas versus Product's long-term vision — but at its core, the divide stems from ego and comfort zones. PMs often use "taste" or visionary purity as shields, avoiding messy real-world trade-offs. That isn't disciplined — it's defensive.

We carry emotional baggage from forced use of clunky, commercially-driven software: punitive expense tools, miserable ticketing systems — products seemingly built by people that hate people. Those experiences leave lasting scars, making us wary of Sales-driven requests.

But casting Sales as adversaries is equally harmful. Product managers who elevate "taste" above business realities aren't defending users — they're protecting their comfort zones.

Mastery emerges from friction. Sales channels market signals no user interview can replicate: the candid realities of operators, frustrated skeptics, and influential advocates. Ignoring these insights isn't principled — it's avoidance.

The Cost of Avoidance

Your beautiful feature competes fiercely for Sales' limited pitch space.

Sales gets maybe ten pitch minutes in a thirty-minute call. The harder it is to explain the ah-ha moments or feel the payoff the more likely it is to be skipped. What do you do? Work with them before the call. Educate, show — don't just tell (or hope they read your one-pagers).

Your feature isn't just competing in the market — it's competing for airtime. Sales will fill their 10 minutes with whatever they can pitch confidently. Technical superiority isn't enough. Distribution clarity wins.

Avoidance breeds also-ran products disguised as principle.

• Missed Insights: Unfiltered Market Signals - Sales conversations reveal exactly what excites buyers, kills deals, or shifts budgets. Calling yourself data-driven while ignoring this isn't principled; it's amateurish.

• GTM Misfires: Your Ideas Don't Sell Themselves - Sales can't sell what they don't understand. If they skip your feature, it's not because it's weak — it's because they lack a clear story. Roadmaps die in silence, not sabotage.

• Confidence Collapse: The Spiral to Irrelevance - When Sales doubts your vision, they undersell as to not ruin their long-term relationship with the customer. When Product ignores Sales insights, they build blindly. Mutual distrust creates products nobody cares about.

Buzzwords Won't Save You: The New Moat

We invoke "craft" and "delight" like scented candles masking indecision. Too often, these buzzwords deflect from lack of validation.

Quality isn't a vibe — it's a commitment to ship things that work, quickly, and make users feel seen.

Delight isn't sparkles and flourishes — it's shipping something useful, usable, and wanted in the market.

Overusing these words becomes product theater and undermines our ability to be seen as leaders. It's how PMs justify ignoring sales feedback — "We're here to delight users, not chase deals." But if you never test whether your "delight" matters in the wild, you're staging a play for an empty audience.

Roadmaps need less vague "vision" and more real market signal — including the uncomfortable insights from Sales.

We romanticize Marketing for polished campaigns and scalable strategy. But Sales is your best high-touch marketing team: real-time, nuanced, revealing true customer desires and objections.

AI-assisted development is shrinking the competitive advantage of product excellence. As product quality democratizes, distribution becomes your primary competitive moat.

Now, customer relationships — not technical superiority — win markets. Who owns those relationships? Sales.

Building Real Partnerships (Without Losing Your Soul)

I learned this lesson deeply leading a technical product. Initially, my team tuned out Sales signals as "not strategic enough." Joining sales calls shifted my perception. Sales' hesitation wasn't strategic — it was confidence. We didn't need another roadmap; we needed better storytelling and collaboration.

Here's your practical checklist for an AI-accelerated world where distribution trumps perfection:

1. Shadow sales calls — listen first.

2. Ask Sales what boosts (or stalls) their confidence.

3. Co-create essential assets reflecting real customer friction.

4. Regularly debrief Sales leadership on market realities — not aspirational roadmaps.

5. Engage actively in Sales' spaces (like Slack channels) as a peer.

6. Test your feature's 90-second pitch — iterate until Sales nails it confidently.

Pro-tip: Have your favorite sales executive elevator-pitch your feature. It'll be humbling and illuminating. If your roadmap can't survive five minutes of sales scrutiny, it's not a strategy — it's a fantasy.

None of this means abdication. Pareto applies: 80% of revenue still comes from 20% of customers. But guess what? That crucial 20% is exactly where Sales spends their time. Ignore them, ignore your best customers.

Invite Bruno to the table — he sees what you don't.

This isn't compromising — it's applying your principles practically, so products get understood, sold, adopted.

Stop hiding behind "vision." Invite Sales out from behind the walls. Excellence isn't proven in your echo chamber — it's validated in practice by those on the front-line.

Not every sales team is a signal goldmine. But your job isn't to blindly follow — it's to synthesize. And Sales offers some of the highest-signal, highest-friction data you'll ever get.

In the AI age, distribution beats perfection. The best product rarely wins — a good product with superior distribution does.

Product mastery isn't avoiding market realities, it's embracing them.

That's how you ship meaningfully, sell impactfully, and build enduringly. Everything else is theater — and you weren't born for bit parts.

Building bridges takes intention, structure, and outside perspective. Ready to transform Product-Sales collaboration? Let's talk. That's exactly the work I help teams navigate.

—
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Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

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—

Note: This one's a bit more personal. Less takeaway, more reflection. Felt right to share it anyway.

A year ago this month, I left Slack.

I left for all the reasons I knew I eventually would, reasons clear to me even before I joined. It happened a little sooner than I expected, but the timing felt right despite the uncertainty ahead. I learned. I grew. I worked alongside some of the smartest, kindest people I've ever known. It was a career highlight in a very fortunate, very lucky run.

And still, I found myself longing for a third vision quest in eight years — with short stints between each.

The first came after I left Betterment. I needed to clear my head, so my wife (then my girlfriend) dropped me off in Italy like a parent at summer camp. We spent a long weekend in Milan, then she waved arrivederci, and I traveled solo throughout northern Italy for ten days. I never planned more than a day ahead. My next meal, bed, and destination were all perpetual questions.

I roamed around speaking little to no Italian (read: none), hunting for off-season cooking classes. The idea came from an episode of Salt Fat Acid Heat — the one where they make focaccia in Liguria. That became the mission: learn to make focaccia, my favorite bread, in Liguria, among olive trees.

I had never traveled alone before. It's a different experience. Beyond always choosing where to eat yourself. You get a lot of time with your thoughts. And the bad part? You get a lot of time with your thoughts.

Solitude strips away the distractions that usually buffer you from yourself. Without meetings to attend or colleagues to impress, I found myself face-to-face with uncomfortable questions I'd been avoiding: Was I building something meaningful or just climbing a ladder? Was I creating things that mattered to me, or just things that looked good on paper?

In between meals, I listened to an audio book about the science of sleep, wondering if I could learn to rest better — to value stillness as much as momentum. The irony wasn't lost on me: even in my escape, I was trying to optimize something.

The second quest came after I helped Casper IPO. I hadn't done that journey before, and I wanted to.

I've always loved cooking. Some of my earliest memories are playing on a blanket in my grandmother's kitchen while my mom and grandma walked around me. After college, I cooked Thursday night dinners for my grandmother. I cooked for friends. For people I loved. I even worked as a recipe tester on the side for the Washington Post food section. The best part? This twenty-nothing year old could expense groceries. Hello, Whole Foods. If the dish was great, I was great. If it flopped, it was a bad recipe. Cooking from a script forces you out of your comfort zone.

Unlike my day-to-day work, cooking was fleeting. You created, consumed, and moved on. Even failures vanished with the plates. You worked with your hands, not just keyboard taps. That impermanence was exactly what I needed after years of building digital products designed to last, scale, and define me professionally.

Heading into my final year at Casper, I started making a lot of bread (pre-pandemic, I was ahead of the curve). One of my close friends, a professional chef, caught the same bug. We took a class, swore allegiance to the metric system, and started experimenting. We made a ton of bread.

I was ready for a break from tech — not just a vacation, but a fundamental shift in how I experienced work. Digital products exist in abstraction; bread is tangible, immediate. So I enrolled in the French Culinary Institute's 8-week bread intensive: forty to sixty loaves a day, kitchen whites, standing all day.

After years of conference rooms and Slack threads, I craved the immediacy of physical work — of going home with flour-dusted shoes and muscles aching from honest labor. I wasn't just tired of my job; I was tired of living exclusively in my head.

Day one was scheduled for April 1, 2020.

So it never happened.

Around that time, I also found out I was going to be a dad. And suddenly, walking away from tech and a steady paycheck felt reckless. The pandemic redefined risk overnight, transforming my career break into something that suddenly felt reckless.

What's strange about interrupted dreams is how quickly they can feel like they belonged to someone else entirely. Within weeks, my culinary school plans became a luxury from another lifetime, fading behind pandemic anxiety and the immediacy of preparing for fatherhood.

During the pandemic on the side, I started a company with friends — a Zoom-based cook-along project called Kitchen Rodeo. We raised over $175k for folks hardest hit by the pandemic. It was the best of times during the worst of times. I met incredible chefs. I was once on a Zoom call with Daniel Boulud, who was wearing two separate AirPods — because he was on another call at the same time. He was kind. I was reminded: people are human.

And somehow, I ended up creating the culinary school I had always wanted to attend. I learned. I practiced a new craft. I was woefully out of my league. And I loved it.

I reunited with friends and former colleagues at Slack just as I welcomed my second daughter. Being present as a dad was my top priority. That proved hard to achieve at a startup. And then I left — a year ago this month.

To do what? I wasn't sure. But I was anxious for a change. I wanted to feel the vertigo of incompetence again — that precipice where growth actually happens. That's always been the pattern: every four or five years, I shift. I mix things up. It's how I keep growing. Each role I've held (engineer, designer, product manager, executive) has added layers to my understanding while calcifying assumptions that eventually needed breaking.

If the first quest was about solitude, and the second about skill, this one … might be about alignment. Or maybe humility. I don't know yet. Maybe that's the point. The third quest didn't start with a passport or a classroom. It started with stillness.

I took most of the summer off. The city is great in the summer — doubly so with young kids. I bought a Burley Honey Bee bike trailer and loaded the kids up for adventures to the park and splash pads. No Sunday Scaries. It felt good to be exactly where my feet were. If my daughter wanted me to color with her at camp drop-off, the answer was easy: of course.

I played a lot of tennis. Much like cooking, it's a comfort from my earliest memories. I hadn't played much since labrum surgery after rediscovering tennis in my late 30s while playing like I was 16. The kitchen and the court: two places I felt most at home.

I tried not to think about work. I wanted to cleanse my palate completely, creating enough distance to feel a genuine longing for something specific rather than just the habit of busyness. I hoped some dormant passion would surface in the stillness, announcing itself with absolute clarity. Instead, I found myself in an unfamiliar state: contentedly purposeless, yet nagged by the suspicion I should be striving toward something.

I was driving without a map, hoping a sign might find me.

I caught up with friends, some in tech, most not. Whether they meant to or not, many were processing similar questions. What's next? Where is all this going? I jokingly called it a mid-life crisis. It wasn't. I'm unbelievably fortunate to be in this position, and I know that. But it was mid-life, and that's humbling.

And maybe, just maybe, I was tired of doing the same thing I'd been doing since I was a teenager, or at least something adjacent to it. That wouldn't be crazy, right?

After Labor Day, I started to feel anxious. Not the productive kind of anxiety that propels you forward, but the stagnant kind that makes you question your worth when you're not visibly producing something. Not sure why then. Maybe it was the run-up to the end of the year. Or the back-to-school energy in the air. But I felt a pull — to do again.

One thing you learn if you're lucky enough to coach people: most of them already know what they want. They're just trying to get comfortable with the decision they've already made.

For me, I realized the constants in all my favorite chapters have been two things: connection and building. They go hand in hand. It's more fun to build with people you care about. So whatever's next, it has to include both.

I started telling friends I was "building the business of Frank." That might be overstating it. Yes, I told them that exactly, but with a wry smile rather than confident bellowing.

"What's that?" they ask. "I'm not sure. I think I want to spend half my time coaching people and half my time writing code."

That was what I wanted, despite prefacing it with I think. If I'm being honest, I probably knew that back in early summer.

With the explosion of AI tools, the creative landscape had fundamentally shifted. Suddenly, the gap between imagination and execution was narrowing daily. A solo builder could now experiment, iterate, and launch ideas that would have required teams just months earlier.

For someone who'd spent years managing increasingly large teams and complex processes, this felt liberating. A return to direct creation, amplified by new capabilities. The prospect of building something meaningful with minimal organizational friction was more than intriguing. It was magnetic.

I started small. Updated my website. Offered free coaching calls, which gradually evolved into paid client relationships as word spread. Leaned into my community. Each day, I wrote code and became a student again. I was busy learning.

September began with two questions:

Would I enjoy spending my days coaching? I'd always guided others on the side, but never as my primary focus. Could I make it an interesting business?

By December, I had my answer to the first question: yes. It wasn't novelty. It was purpose. Working with someone one-on-one, watching them clear hurdles they once thought impossible. There's magic in that moment.

When someone chooses you — I want to get better, and I want you to help me — it creates a different energy than managing direct reports. They're all in. And so am I. That's the reward.

It took me five months before I updated LinkedIn. Five months of helping others navigate their careers while hesitating to publicly acknowledge the shift in my own. I told myself I was just being cautious, testing the waters before committing. But something deeper was at work. For years, my identity had been tied to well-recognized companies and established roles. To step away from that framework meant facing questions I'd been avoiding: Who am I without those institutional affiliations? What if people don't value what I offer when it's just me, without the backing of a recognized brand?

In college, my roommates were musicians who regularly performed publicly. I'd watch them put their creations out there, completely exposed to praise or indifference. I admired that courage. The willingness to be seen creating something personal, something that might fail.

Updating my LinkedIn felt like my own small version of that vulnerability. It was publicly claiming an identity outside the safety of established roles and recognized companies. It meant saying: this is me now, without the institutional armor I've always worn.

I wrote this because I needed to write it. Because I needed to hear it. Anniversaries are a natural time for reflection. I was on a podcast recently, and the host said their company thinks of a job search as a hero's journey. I liked that idea.

Looking for a job or figuring out your next chapter isn't time out of your life. It's a part of your life. A chapter worthy of the same attention and dignity as any title or job. It's a journey worth exploring.

So did the third quest end?

Not exactly. But I stopped wandering off-course, looking for someone else's map. I stopped searching for answers that weren't mine to find.

And that feels like progress.

—
Have a topic you'd like me to explore? Drop me a line and your idea could be featured in an upcoming newsletter.

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

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—

Remember that feeling of senioritis? That sweet spot after exams but before graduation. The weight's lifted. You're looser, bolder. Like you could probably dunk or at least convince yourself to try.

In the working world, there's a version of this too: when you've announced you're leaving but haven't left yet. The air feels different. Colleagues knock on your door to talk. You have some of the best conversations of your tenure. The vibes are good.

But not every ending is a celebration.

The more senior you get, the more you realize: most roles don't end with a standing ovation. They end with a quiet shift of attention elsewhere. A team's energy moves on. One day you're at the center of the room. The next, the room has reoriented itself and you're standing by the door.

And yet, you can still feel a weight off your shoulders.

It's not failure. It's not even personal. It's just how leadership — and careers — actually work.

Walking the Course Backward

I learned this lesson early. Not in tech. On a cross-country course.

In high school, I ran cross-country to stay in shape for tennis season. I wasn't the fastest on the team, so I was always looking for an edge. I had a ritual for every new course: I'd walk it backward, starting at the finish line.

I wanted to know exactly how it ended. Where the brutal hills hid behind blind corners. Where the trail turned from gravel to soft dirt. Could I make a pass here? Where the crowd thinned out, and it would just be me, my legs, and my lungs.

Knowing the end didn't make the race easier, it made it clearer. I could pace myself better. Push when it mattered. Block passes at the right corners. I didn't waste energy pretending the hill wasn't coming — I planned for it.

That practice turned uncertainty into strategy. It made the invisible visible.

Leadership Terrain Is Always Moving

Leadership roles are built on shifting ground. After all, leadership roles exist because of the absence of and the opportunity or desire for more.

In some leadership roles, you're lucky to last longer than a college quarterback. NCAA coaches average just 3.7 seasons in Division I football. Nearly 70% of head coaches won't outlast the players they recruit. And they're expected to win while building the team that replaces them.

The terrain shifts fastest under leaders responsible for customer satisfaction, product success, and market performance. There is one throat to squeeze, and it's yours. If it's that way on top, there's always a ripple effect below.

That realization doesn't make you cynical. It makes you clear-eyed. It frees you to stop performing for permanence.

The real leadership race isn't a marathon. It's a relay. Your job isn't to cling to the baton forever. It's to run your leg brilliantly, and pass it stronger than you found it. That's it.

You push when it matters. You create value. You stand your ground when it's right. You invest in people and systems, not just perception. You build for the long term, even if you aren't the last person standing.

This isn't just theory. Remember that senioritis freedom I mentioned? It's real in professional exits too. After resignation, the filters come off. You give unvarnished feedback, coach without hedging, name systemic issues directly, and focus on substance over politics.

Research confirms this phenomenon: studies in The Open Psychology Journal and Harvard Business Review show psychological safety spikes when employees know they're leaving. They finally speak their full truth.

A Moment That Changed How I Led

I didn't always see it this way.

Years ago, I led product at a growing startup. I had a strong team, meaningful work, and we were making progress, though never quite at the pace investors wanted. The CEO, doing what CEOs should do, was constantly exploring different growth levers.

Every quarter, we'd discuss potential reorgs. Each time, I'd spiral: How would this affect the roadmap? My role? My team? My influence? I'd spend precious mental energy gaming out scenarios, preparing defenses for decisions that hadn't even been made.

The anxiety was exhausting. Worse, it was distracting me from actually leading. Instead of focusing on the race I was running, I was constantly looking over my shoulder. I was playing defense when my team needed offense.

Then one day, what I'd feared happened. A major reorg was announced without my input, effectively sidelining my position. But strangely, instead of panic, I felt... clarity. The thing I'd been dreading had arrived, and suddenly I wasn't wasting energy fighting shadows anymore.

That's when a simple truth hit me: this wasn't my company. I had influence but not control. No amount of worry would change decisions made above me. Once I truly accepted this, it was liberating.

With nothing left to protect, I could focus entirely on ensuring a smooth transition and finishing strong. The irony was striking: when I finally accepted that every role is temporary, I gained the freedom to lead authentically. I stopped calculating "will this help me stay longer?" with every decision.

Running a Smarter Race

The research confirms what experience taught me: accepting the temporary nature of your role doesn't just prepare you for the end. It transforms how you lead right now.

Herminia Ibarra's work shows that leaders who hold their roles with open hands rather than clenched fists demonstrate greater creativity and risk tolerance. Studies in the Frontiers in Psychology reveal that this acceptance mindset correlates with higher resilience and lower stress in the present, not just during transitions.

This mindset shifts your leadership in immediate, tangible ways:

• You make decisions based on what the business needs — not what protects your title.

• You have difficult conversations today — instead of postponing them until "someday."

• You build systems that scale — beyond your personal bandwidth.

• You develop your team for their futures — not just your current needs.

• You focus on lasting impact — not temporary approval.

The most liberating truth isn't that all roles eventually end. It's that accepting this reality frees you to lead more boldly while you're still in them. You become dangerous in the best way: a leader anchored to values rather than fears, focused on impact rather than tenure.

Closing the Loop

In leadership, the most important moves happen long before the final sprint. They happen in how you read the course. How you pace yourself. How you work today, knowing you won't always be there tomorrow.

I once had a boss that would repeatedly tell me, "You know I don't need this job." It was a strange flex from a serial entrepreneur with multiple exits. I'd think, "I get it, but I need this job. Why tell me?"

Perhaps it wasn't just a flex but his coping mechanism. His way of claiming freedom in uncertainty by speaking it into existence.

You might not get the sunset ending. You might not hear the applause at the exact time you want.

But the only thing worse than the race ending is not running your race, your way, all the way to the end.

—
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Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

Join my referral program and earn 1:1 coaching sessions by sharing Frank Takeaways with others - start with just three referrals.
—

I recently caught up with a friend, reminiscing about a past PM job and the day we got pulled into a conference room. It’s hard to remember the details — the meeting was anything but specific or uncommon. Someone had scheduled a “PM sync.” No agenda. No objective. Just a vague sense we should “connect.”

We were all reasonably experienced, knowing what we were doing and, at the same time, still figuring it out. Some of us ran businesses. Some of us ran platforms. Some focused primarily on the consumer experience in-between. The wildest part? Not one of us could tell you why we were there or what we were meant to do together.

So we did what PMs do when things don’t make sense: we asked a few questions, complained a little, and looked for our Irish exit.

It felt like a high school reunion with people you weren’t close to the first time around. Everyone vaguely familiar. No deep shared memories. No real reason to be there, except someone else thought we should be.

It reminded me of that line from About a Boy (with apologies to John Donne): “Every man is an island. And what’s more, he’s an island paradise. He’s Ibiza.” That’s what PMs are supposed to be, fully autonomous, fully optimized. But in practice, it’s more like trying to run an archipelago without any bridges. We’re alone together.

It wasn’t a one-off. I’ve seen it again and again at companies big and small: product leaders try to create cross-PM rituals — a sync, a council, a round-table, and it fizzles. Quickly.

The Interview Disconnect

It didn’t start this way. Remember the interview? We spend hours trying to evaluate a candidate’s product sense before they join: case studies, frameworks, strategy whiteboards. And then?

They get the job, and we mostly stop talking about product, at least in the theoretical sense.

The work becomes local. Tactical. Focused on launches, not learning. We interview for taste and judgment, but once hired, there’s rarely a forum to develop those muscles further.

This isn’t just a missed opportunity — it’s a risk. Critical thinking is like a muscle: without challenge, it atrophies. In one study, participants who spent just 15 minutes reflecting on their work daily outperformed peers by 23% after 10 days.

As John Dewey put it: “We do not learn from experience… we learn from reflecting on experience.” Donald Schön extended this: reflection-in-action (while doing) and reflection-on-action (after doing). PMs need both.

So why don’t we create the space to keep thinking?

Schedule the Mess

Rituals are how we encode values and beliefs.

Consider Netflix: Former VP of Product Gibson Biddle introduced a product strategy ritual where every team shared what they were learning, why it mattered, and what bets they’d make next, not just polished outcomes. Strategy docs were shared in advance and debate was expected. Half presentation, half critique. Alignment was earned, not mandated. The goal wasn’t consensus — it was context. Over time, this ritual reinforced Netflix’s culture of candor and strategic thinking, built on frameworks like Biddle’s DHM model: Delightful, Hard-to-copy, Margin-enhancing.

It's not just Netflix. At Coda, the monthly "Garden Party" welcomes anyone, regardless of role, to pitch product ideas. Pixar's Braintrust gives directors a space for candid peer feedback, without formal authority. Again, the result wasn't consensus but clarity.

Why do these rituals work, when so many PM syncs fizzle? Because they're not theater. Not update parades or awkward silences. They're spaces for work in progress: unfinished thinking, sketchy strategies, fuzzy trade-offs. The mess, not just the metrics. They center around real work that's useful first and foremost to the presenter and then the audience. In other words, they're worth their time.

The other core ingredient? Psychological safety. As Amy Edmondson notes, this is the belief you can raise tough ideas, ask naïve questions, and share risky insights without reputational risk. Google’s Project Aristotle found it to be the most important factor in effective teams.

Structure matters, but intent matters more. Whether it’s Netflix, Coda, or Pixar, these rituals thrive not because they’re polished, but because they foster the messy middle — where product sense is tested, challenged, and honed.

Miss this, and your strategic muscle weakens. Your best PMs become only execution machines (isn’t that what AI is for?). Your product flattens out.

Caveat Emptor I and II

Caveat Emptor I: Frank, PMs aren’t just stretched too thin, they’re rubber bands starting to snap.

Between backlogs, stand-ups, reviews, decks, stakeholder updates, and surprise "quick questions," the idea of carving out more time to reflect, prepare for a strategy session, or simply think? It feels laughable.

In a ship-ship-ship culture, thinking starts to feel like a luxury.

But here’s the trap: if all we do is execute, our thinking degrades. And so does the product.

So the answer isn’t “add more meetings.” It’s to build smarter rituals — ones where the discussion is the exhaust of the work itself. That one-pager you wrote for leadership? That’s the thing we discuss. That roadmap trade-off you just debated? Use it as a live case study.

Great rituals don’t require extra prep. They just require structure, rhythm, and a team agreement that sharpening our thinking is part of the job.

And as leaders, it’s on us to make that real.

• To protect space for deep dives.

• To model the pause.

• To ask better questions — not just for answers, but for insight.

Because the truth is: shipping and sharpening aren’t at odds. In the best teams, they feed each other.

Caveat Emptor II: Frank, as leaders sometimes I need to communicate things to my team. I think readouts are valuable. Don't you dare take away my readouts.

I agree, readouts have value. Just don’t let them hijack the whole meeting. Start with a crisp five-minute “top-of-mind” share: “Here are things you need to know. No need to react now — just digest and apply where relevant.”

Readouts bridge silos and connect product to business context. The key? Honesty. Call one-way information what it is. It feels disingenuous when readout theater masquerades as collaboration.

The best ones are brief, clearly framed, and serve the product conversation without trying to become it.

Iron Sharpens Iron

Design has critiques. Engineering has architecture reviews. They pressure-test the work before it ships.

So why don’t PMs do the same?

Too often, we only share when the story’s finished. Or we ask for feedback from only the people closest to the work — not the people whose product sense we admire.

Let’s fix that:

• Pick a recurring slot. Monthly or biweekly, whatever fits, and give it a low-pressure name: “Product Problem Hour,” “Thinking Aloud,” whatever lowers the stakes.

• Make it opt-in but visible. Bring one messy, in-progress challenge: a half-formed strategy, a roadmap trade-off, or a tough call.

• Set one ground rule: This space exists to sharpen thinking, not present finished work.

• End with action: Each session, help the presenter walk away with a next step or new clarity.

• Rotate facilitation: Spread ownership, keep it fresh. It has to be valuable first and foremost to the presenter.

• After 1–2 sessions, check in: Did this sharpen our work? If not, tweak and try again.

Leverage tools or AI to document and connect ideas if it lowers friction, but don’t let the tool replace the talk. The magic is in the conversation itself.

Want to sharpen product thinking? Model on Pixar’s Braintrust: focus on the problem, not the person; let the presenter decide what to do; keep feedback expert but non-authoritative.

A Cautionary Tale

On Pentecost Island in Vanuatu, there’s a ritual where men leap from 100-foot towers with vines tied to their ankles. It’s called land diving. The aim? To brush the earth with their heads and bless the soil for a good harvest.

Anthropologists say the ritual began with a woman outsmarting her husband by tying vines to her ankles before a desperate jump. He followed, unprepared, and didn’t survive. The lesson lived on: every year, men rebuild the tower, select the right vines, and leap — if the timing and conditions are right.

Here’s the catch: land diving only works when the details are honored. In 1974, the ritual was performed out of season to impress Queen Elizabeth II. The vines were brittle. One snapped, and a diver died. Symbolism turned fatal because the context and care were ignored.

Our work is similar. In product management, we build our own towers of ritual — strategy councils, syncs, show-and-tells. But the risk isn't just that these become performative. Save the look-backs and book reviews for the all-hands. Great theater, but if that's all you're doing, you're missing what matters. Product minds crave more than connection — they hunger for relevance, for strategic dialogue, for the chance to sharpen their craft together. Without attention and intent, we start leaping for tradition's sake, missing the real point. Are we designing the leap, or just following the script?

Just like the land-diving tower, our work rituals require continual rebuilding and re-calibration. What worked last year may be dangerously out of sync this year — the “vines” too brittle for today’s realities.

So as you look at your own product rituals, take a closer look at the vines. Are they still elastic, built for where you want to go? Or are you making a leap out of habit, hoping tradition alone will catch you?

The best teams I’ve seen don't just leap and hope. They build, rebuild, and check their ropes every time. Not for show, but because they know the real work — the real leap — only matters if you land safely, together.

Because no PM is an island. No leap is just symbolic. And none of us should be building alone.

—
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Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

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—

Fifteen minutes into a recent coaching session, a product lead at a Series A startup leaned forward and lowered her voice:

"Everything feels off. Am I crazy?"

She wasn't crazy. She'd just seen — or maybe better said, felt — greatness before. And now she was feeling its absence without quite knowing how to name it. This is the strange terrain you enter after experiencing higher standards. Nothing's broken — it's just that the contrast is gone.

More than a decade ago, Joe Kraus wrote a piece that I keep revisiting. The title said it all: "If You Don't Think You Need It, You Haven't Seen Greatness."

His point was simple, whether about product marketing, legal, or any other role: once you've seen greatness, you can't go back. You stop questioning whether that function is "worth it," because now you know what it unlocks.

That's just it. Greatness ruins you in the best way.

Psychologists call this the contrast effect — your sense of what's "normal" shifts based on past experiences. Going from a high-performing environment to a merely good one feels like moving from a symphony to a garage band. The garage band isn't wrong — you just can't un-hear the symphony.

I've felt this myself. Moving from Google to a startup and then to another, I kept having these moments where I'd suggest something basic — like a structured decision doc or a launch calendar — and people would look at me like I was some kind of organizational genius. I wasn't. I'd just been somewhere where those things were standard operating procedure.

It's like living in New York for years, then moving to a small town and wondering why no one delivers Thai food at 11pm.

The problem isn't the town.

The problem is that you've experienced a different standard — without realizing it was special.

Welcome to the Grown-Up Table

One of the weirdest parts of leveling up in your career and joining a new team, company, or role is that the problems start showing up as vibes.

You step into the new place, and everything feels heavier. Slower. Messier. The tools are there, your co-workers are smart and friendly, so why does everything still feel off?

Because your body noticed what was missing before your brain caught up.

Cognitive scientists refer to this as expert intuition, your subconscious spotting patterns (or absences) before your conscious mind can name them. You're not "overreacting"; you've just developed an inner compass tuned by past excellence.

This leader had operated in more mature orgs before, ones where product and sales had a rhythm. Where cross-functional partnerships were more than a formality. Where feedback was a given, not a surprise. She had seen greatness. She just didn't know to name it as such because back then, it was the air she breathed.

Now she was in a company where that air was thinner. Not toxic. Just… less oxygen. The disorientation that followed wasn't because anything was broken, but because there was no contrast. Without that, it's easy to think the discomfort must be coming from you.

And here's what truly messes with your head: your discomfort is often invisible to everyone else. Not because they don't care, but because they've never breathed that richer air. You're noticing the absence of greatness while they're experiencing what they consider normal.

This invisible gap is why your suggestions might be met with confusion rather than enthusiasm. You're not imagining things — you've just developed a calibration that others haven't had the opportunity to acquire.

You're not being too precious. You've just been to the mountaintop, and now you're stuck explaining snow to people who've only lived in the desert. It's frustrating, but it's not a red flag — it's your cue to lead.

Building the Playbook (While You Run)

Have you ever said, "I feel like I'm working on a bunch of stuff, but I'm not sure any of it matters."

You were executing. But it all felt fuzzy. Like you were applying first principles with no clear direction in sight.

You're craving context. At a Series A, that means knowing exactly what you need to prove for Series B: What's the strategy? What's the bar?

And here's the hidden tax of leadership: you're not just there to operate inside the system — you're often building the system itself. That's the sneaky shift: leadership moves from doing the work to designing the systems that make work possible. Suddenly, the playbook feels like it's missing pages because, well, you're writing some of them as you go.

You used to rely on senior leaders to push you. Now you are the senior leader. No one's going to tell you what the standard should be, push for that weekly leadership sync, clarify the difference between goals and strategy, or suggest a cross-functional touch point. That's your job now. And it's weirdly hard to accept, especially when everyone's friendly and "figuring it out."

Confession: When I first became a senior leader, I waited months for someone else to set the strategy or start hard conversations until I realized that ‘someone’ was me.

The good news? You don't have to get everything right. But you do have to start modeling what right looks like.

Leading with Empathy (Even When the Air Feels Thin)

It’s tempting to assume others don’t care or are fine with “good enough.” Usually, that’s not the case — they simply might not have experienced what "great" looks like.

Most people genuinely want to do meaningful work. Resistance or indifference often masks uncertainty, discomfort with change, or unfamiliarity. Your job isn't just raising the bar — it's patiently showing others what's possible.

One powerful phrase: “I think this might help us, but if not, let’s revisit it in a month.” This shows you're invested in collective success, open to feedback, and willing to adjust if needed.

Lead with empathy, not just standards. That’s how you find fellow founders, not just followers and how greatness quietly takes root.

How to Teach Snow in the Desert

Teaching snow in the desert isn’t about delivering a blizzard overnight — it’s about helping others sense the coolness in the air. Each small, strategic action you take is another flake, quietly showing everyone that something different is possible.

Think Ted Lasso, not Ted Talks.

Like asking why product isn't invited to the go-to-market meeting. Suggesting a joint plan with your sales lead. Or pointing out that a roadmap isn't a strategy.

If this is resonating, here are a few micro-actions that help build that new climate:

Don't confuse strategy with projects

A goal is what we want. A strategy is how we think we'll get there. Projects are bets we make to test that strategy.

A company in Series A might not have this codified. That doesn't mean it shouldn't exist. Start with a hypothesis: "We believe we'll grow by focusing on X segment using Y advantage." Then check if your projects are laddering up. Even a one-pager with this logic can orient a team used to wandering in the dark.

Create contrast where none exists

You don't need to overhaul the culture. Start by adding a signal.

Try a monthly launch review or a short, opinionated write-up on how product and GTM can partner. Maybe create a list of the 5 questions every customer should be able to answer on your homepage.

Each signal becomes a little weather change, cloud by cloud, showing others that something new is possible.

Build allies, not just processes

The loneliest part of being "the one who's seen greatness" is feeling like you're the only one who cares. Find your fellow standard-bearers:

That frustrated sales leader, the engineer who appreciates clear requirements, the designer who wants to build systems rather than just screens.

Greatness spreads through networks, not mandates.

Your fellow "greatness carriers" are out there. If no one else has seen greatness before, make it visible.

This isn't just intuition — organizational change research underscores that small, consistent actions plus allies — not just process docs — drive real, lasting change.

Ready to help others feel the shift? Start tomorrow with one clear, small action:

• Schedule the very first cross-functional launch demo.

• Ask explicitly in Slack, “Who else needs eyes on this before we ship?”

• Create a one-pager explicitly linking a project back to strategy.

The Gift of Feeling Crazy

If you've ever found yourself asking, "Why is this so hard?" you're not alone. You're ahead of the curve. The discomfort isn't failure — it's awareness. You've seen better. That's a gift.

And if no one else recognizes what's missing yet? That just means you get to be the one who names it. Just like you can’t go back once you’ve seen greatness, once you've shown greatness to others, they can't unsee it either.

Eventually, you may wonder if it’s time to find a place that matches your standards rather than continually raising them alone. If thoughtful attempts keep hitting walls, trust your instincts and remember how greatness feels.

So yes, it feels weird now. Good. That’s your cue. You're not crazy — you're just first to notice the air thinning. Good news: you get to open the window.

Opening that window might start with the smallest breeze — one question, one meeting, one document — but soon enough, you'll feel the air shifting around you. That's how climates change.

The disorientation isn’t a sign of weakness, it’s proof you’ve lived and learned in rarefied air.

What's one moment you realized you'd been quietly spoiled by greatness? Drop a comment — I'd love to hear it.

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

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—

The first time I wrote code, it wasn't for a computer — it was for a calculator. It was my introduction to the endless debate about technology and human potential. Stop me if this sounds familiar.

I still remember my AP Calculus (hold your applause) teacher allowing us to bring one index card with notes to tests. "Can we write on both sides?" Penmanship had never been more important. Little did I know that those index cards were just the beginning.

Soon our teacher allowed an even more powerful test companion: the crowning ed-tech device of the 1990s — the graphing calculator. The TI-82 was standard, the TI-83 was the stylish upgrade, and the TI-85 was for hardcore math nerds. When we weren't typing 58008 to spell BOOBS upside down, we were using them to load our cheat sheets.

It was the first device I programmed, and like today's AI tools, it sparked fierce debates about human capability and technological dependence. And here’s the thing: Yesterday’s calculator panic offers a blueprint for understanding today’s AI anxiety and why we might be worrying about the wrong things.

Congrats, Your Tools are Sharp

We often think tools just make us faster. With my Texas Instruments, I could do more math problems in one hour than before. But the real transformation happens when tools change what we believe is possible.

The evidence challenges everything skeptics feared: Fourth-grade teachers who reported their students used calculators daily or weekly had students with the highest test scores on the 1996 NAEP assessment, while teachers reporting no calculator use had students with the lowest scores — even though the assessment itself prohibited calculator use. Students with graphing calculators showed increased willingness to tackle challenging problem-solving activities that might otherwise have seemed intimidating. They weren't just working faster — they were thinking bigger.

What's particularly instructive is how educators adapted as the cat was out of the bag. Rather than banning the technology, NAEP evolved their approach — shifting focus from computation to "mathematical complexity," developing "calculator-active" questions that leveraged technology while testing understanding, and maintaining a balance with calculator-inactive sections. The goal wasn't restricting tools but redesigning assessments to measure deeper conceptual mastery, regardless of the tools used.

The most compelling finding? Students who understood when and how to use calculators effectively outperformed both those who relied on them blindly and those who avoided them entirely.

The tool itself wasn't the advantage. It was knowing how to think with it.

Don’t Be an AI Doomer, Boomer

I can hear you now: "Sure, Frank, but calculators just crunch numbers — AI can think and reason. It writes poems, designs logos, writes code, drafts legal briefs." Fair point. The leap from computational tool to cognitive copilot feels more threatening, more fundamental.

But if my TI-83 was the first tool that changed how I thought, AI is just a more powerful iteration of that same revolution. It's not just about what the tool can do — it's about how it transforms what we believe we can accomplish.

Remember when I mentioned programming my TI-83? That simple TI-BASIC code I wrote to solve quadratic equations was my first taste of automation. It wasn't just about getting answers faster — it was about teaching the machine to think through a process I understood. Today, developers do the same thing with AI, but at a vastly different scale. Instead of programming step-by-step instructions, they're teaching AI to understand context and intent.

Yes, the difference in capability is vast. But the pattern is familiar: When AI is used within its capability boundaries, it improves skilled worker performance by nearly 40%. Push beyond those boundaries, and performance drops by 19 percentage points. Just like calculators, success comes from understanding the tool's limits and possibilities.

Survival Guide for the Merely Human

When tools advance, human expertise doesn't diminish — it evolves. Here's what that means for today's knowledge workers:

Then: Excellence meant mastering the mechanics — the raw computational skills.
Now: Excellence means mastering the context — knowing which problems need solving.
Next: Excellence will mean mastering possibility — understanding what we can dare to attempt.

I witnessed this pattern firsthand during my time at Betterment. Alongside other robo-advisors, we watched this familiar story unfold. When automated investing platforms first launched, headlines screamed about the death of human advisors. After all, a computer could now handle asset allocation and re-balancing — tasks that traditionally justified hefty fees.

But something interesting happened: Automation didn't replace advisors — it elevated the best of them. While algorithms handled the math, advisors devoted more time to the messy human stuff: life decisions, money anxiety, uncertain futures. They weren't just managing portfolios; they were expanding what financial advice could mean.

This mirrors what historian Ruth Schwartz Cowan observed in her groundbreaking book More Work for Mother — tech innovations rarely eliminate work. The washing machine didn't just erase laundry day; it transformed what "clean" meant, creating new standards and expectations. Doing laundry is so accessible, we should do it more often. It’s so easy to do laundry, your clothes should always be impeccable.Similarly, AI won't just subtract tasks — it will reshape our expectations. Or as my brilliant wife coined, “Machines = higher standards of cleanliness not less work”.

Just as students with calculator access tackled more complex mathematical challenges, our advisors could now address more sophisticated client needs.

So what does this mean for today's AI revolution?

Understanding surpasses execution. Just like calculator users needed to grasp mathematical concepts, AI users need deep domain knowledge to use it effectively.

Context is king. The most valuable skill isn't generating content — it's knowing what should be generated and why. Research shows even skilled professionals struggle to determine which tasks to delegate to AI. Just as calculator users needed to know which functions to graph, AI users need discernment about which problems deserve attention. The strategic framing of work now outweighs its execution.

Verification is vital. Students who blindly trusted calculators failed. Similarly with AI, optimal results come only when workers critically evaluate outputs rather than accepting them at face value. This isn't just double-checking — it's developing what Evan Armstrong calls "good taste": the refined judgment to distinguish between adequate and excellent. The valuable skill isn't producing work; it's recognizing quality when you see it.

Plot Twist: We Get Better Too

That TI-83 is long gone now, but I can still feel its weight in my hands and how the front cover slid and clicked into place. I remember the feeling when our teacher first allowed them in class. Now it feels like a reminder: every generation's "cheating" is the next generation's baseline.

Here's what simultaneously terrifies and excites me: AI today is as dumb as it will ever be. The research shows you could be 40% more effective when you use it right — and that's just the starting line.

Recent studies suggest a warning worth heeding: heavy AI users show diminished critical thinking skills compared to light users. Called "cognitive offloading," it happens when we delegate our thinking instead of enhancing it. That said the researchers found that AI tools can be beneficial when they complement critical thinking rather than replacing it. Sound familiar? It's the calculator lesson all over again. tldr; It’s a tool. Use it wisely.

So, how do we actually build these skills?

Start small. Choose one routine task in your workflow that's well-defined and easily verifiable: perhaps drafting routine emails, organizing meeting notes, or generating first drafts. Master that before moving to more complex applications.

Next, join communities of practice. The calculator revolution didn't happen in isolation; it spread through classrooms and study groups. Find others in your field experimenting with AI and share what works. This could be a Slack channel at work (hint: create one if it doesn’t yet exist) or a sub on Reddit. Trade tips, find new ones. Bring others into the fold. Learn.

Finally, reflect. What tasks have you delegated to AI? In full or partial? Which ones have you reclaimed? The goal isn't maximum delegation but optimal partnership.

So here's my challenge: Instead of fixating on what AI might take away, ask yourself what you might become with it. Just like that calculator in math class, we're not merely learning to use a tool — we're expanding what's possible, training ourselves to think and dream bigger.

AI will keep getting smarter. The real question is: Will you?

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

Join my referral program and earn 1:1 coaching sessions by sharing Frank Takeaways with others - start with just three referrals.
—

The crowd at DC's 9:30 Club was drenched in sweat, voices hoarse from singing on a cold Sunday night in early 2005, where a light snow had fallen outside.

Arcade Fire had just played the final notes of "Rebellion (Lies)." The roadies moved toward the stage, but nobody else moved. Instead, the stomping began: first from the back, then rippling forward until the entire venue pulsed with a collective demand: more.

This wasn’t just any concert. It was Arcade Fire’s only show at the legendary 9:30 Club, just months after the release of Funeral. They were on the verge of blowing up. Next time they’d play in DC, it would be at a much larger venue.

But that night, eight musicians crowded the small stage, swapping instruments, pounding drumsticks on motorcycle helmets, climbing speakers like the room couldn’t contain them. Kick drums you could feel in your bones, Win Butler and Régine Chassagne’s unmistakable vocals cutting through it all.

When the band returned for their encore, they didn’t just play another song. They found another gear — somehow surpassing the energy they’d already poured out, when logic said they should’ve been spent.

To close the night, during "In the Backseat," they descended from the stage and wove through the packed venue — yes, with the kick drum in tow — first through the sea of humanity on the main floor, then ascending to the balcony. Their voices melded into one haunting chorus as they disappeared behind the stage.

Years later, what strikes me most about that night isn’t the music (it’s not like the lyrics are easy to understand or the rhythms particularly complex). It’s watching performers who had already given everything give more.

Which brings me to the elephant in the interview room: we’re living in an employer’s market, and it’s getting crowded in here. Landing a dream job (or any job, amirite?) feels less like a sprint and more like an ultra-marathon. But while everyone’s obsessing over resume fonts or LinkedIn headlines, they’re missing something far more important.

The Great Energy Equation

Tell me if this sounds familiar: You’re on your fifth Zoom interview for a role you genuinely want. The calendar reminder pops up, and you feel that familiar weight of the fatigue of explaining your "career journey" so many times you could recite it in your sleep. You catch your reflection: tired, rehearsed, slightly defeated. And then it hits you: this hiring manager doesn’t know you’ve told this story four times already. Ten times this week. For them, this is opening night, not a rerun — tell me about a time when you didn’t zone out in an interview.

Now picture the hiring manager’s view. They’re sifting through resumes that all read like they were generated by the same AI. Everyone’s qualified. Everyone has the right keywords. So what tips the scales?

Here’s the secret: It’s not just what you know or even who you know. It’s how you show up.

When qualifications are nearly identical — and in this market, they usually are — your energy and enthusiasm become your unfair advantage.

The Second Wind Strategy

That's where the magic happens. The best candidates treat each retelling like an encore.

The concert encore has a fascinating history. In the 18th century, audiences would demand their favorite pieces "again" — literally what "encore" means in French — because there was no recording technology.

It was the only way to hear your favorite song again. Over time, encores became ritualized, choreographed into every show. They moved from during the set to after it. But even when they're expected, encores still serve a purpose: they create a closing moment, make the audience feel seen, and leave everyone on a high note.

Think about Bruce Springsteen singing "Born to Run" for the millionth time. He doesn't phone it in because he's tired of the song. He brings opening-night energy every time because every audience deserves it. (Bruce Springsteen is often credited with developing the modern encore into a "second show"-like experience.)

I've been on both sides of this equation. As a candidate, I've bombed interviews when my energy flagged during the seventh retelling of my stakeholder management story —and watched the hiring manager's interest fade in real time. But as an interviewer, I've been captivated by candidates who somehow make rehearsed answers feel fresh and alive, who lean forward and light up when describing their work. That energy is contagious and it makes me want them on my team.

The Human Factor

Every hire is a risk, even in boom times. When employers are increasingly risk-averse, what tips the scales? In addition to relevant experience, they scan for signs of commitment, chemistry, and energy. They want to know: Will this person show up when things get hard?

Instead of asking, "Can this person do the job?" They're asking, "Have they done it before — and do they want to do it here?"

I've sat in plenty of hiring debriefs for product roles where two candidates had similar qualifications. You know what broke the tie?

"Candidate A was solid, but they seemed kind of flat."
"Candidate B asked great questions. They had clear enthusiasm about our user problems and product challenges. They seemed excited to be here."

Nine times out of ten, Candidate B got the offer. Not because they were objectively better. Because they made us believe they cared about the same things we care about.

As Shopify’s CEO and co-founder Tobi Lütke once said: "It is not possible to make great products if the people who work on it do not give a shit about the product." And the same goes for job candidates. Enthusiasm is evidence you’ll care about the work.

Sometimes, enthusiasm even outweighs direct experience. I once hired someone new to product management who had only worked in adjacent areas like customer success. What stood out wasn't their product experience (they didn’t have any) — it was their unmistakable passion for solving user problems. Their energy was contagious during interviews, and they articulated a clear vision for how they'd approach the role.

I was unsure about the hire. Yes, they had enthusiasm in spades, but was it enough? Looking back, it was one of the best hiring decisions I've made. They started in an area that allowed them to build foundational skills, but their enthusiasm propelled rapid growth. Before long, they outgrew their initial role and were chasing bigger challenges.

The Enthusiasm Edge

In a crowded job market, genuine enthusiasm isn't just a nice-to-have — it's your secret weapon. Here's how to wield it effectively without coming across as performative or insincere:

What does that look like?

✅ Thoughtful, specific questions
✅ Speaking about past projects with genuine pride
✅ Acknowledging challenges openly and focusing on how you navigated them
✅ Expressing curiosity about the team, product, or culture
✅ Following up with reflections that show you were paying attention

What it’s not:

🚨 Over-rehearsed, robotic responses
🚨 Low energy or disinterested tone
🚨 Generic answers that could apply anywhere
🚨 Focusing only on what you’ll get, not what you’ll give
🚨 Treating interviews like interrogations, not conversations

Remember: The goal isn't to perform enthusiasm but to connect your genuine interest to their specific needs. When you find the intersection between what energizes you and what they need, that's where the magic happens.

The Only Thing You Control

You can't control the job market, the competition, or whether anyone reads your cover letter (most likely not). But you can control how you show up.

Early in my career, I interviewed for a role I desperately wanted. I approached it with a "professional" demeanor I thought would impress — measured, serious, frankly dull. I didn’t get the job. Months later, I ran into someone on the hiring committee. When I asked about my candidacy, their response surprised me: "You were really qualified, but we weren’t sure you actually wanted to be there."

That feedback stung — but it changed how I approached every interview afterward.

Like the modern encore, your interview performance may feel rehearsed to you, but it’s fresh to every new audience. The hiring team hasn't heard your stories before. For them, it's opening night. Give them a show worth remembering.

So the next time you’re prepping for round five of interviews, channel your inner Springsteen or remember that night at the 9:30 Club, when a band that had already left everything on stage somehow found more to give. The curtain’s up. The mic is hot.

Make every performance count.

—
Bonus: Here’s the only video I could find from the night:

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

Join my referral program and earn 1:1 coaching sessions by sharing Frank Takeaways with others - start with just three referrals.
—

Bad managers turn simple requests into bureaucratic nightmares, hoard information, and vanish from meetings only to resurface when credit is due. They dismiss thoughtful proposals with "Let's take this offline" and make inexplicable decisions that leave you questioning your sanity.

Bad management is like the weather — unpredictable, sometimes disastrous, and mostly out of your control. Some managers rain chaos. Others bring the heat but no direction. And every now and then, you get one who's a perfect climate for growth. But don't be an orchid: the professional who can only thrive under ideal conditions.

The Accidental Manager Factory

Many companies promote high performers without adequate training, assuming execution excellence equals leadership excellence. The result? The 'accidental manager': not bad on purpose, just unsupported and unprepared.

The recipe is simple:

• Take one high-performing individual contributor

• Add a dash of organizational necessity

• Promote them without training

• Season with impossible expectations

• Garnish with no support system

Cost-cutting makes it worse: expanding manager-to-employee ratios leaves unprepared leaders drowning. A no-win scenario.

The numbers are staggering: 91.3% of managers report receiving little to no formal training before taking on leadership responsibilities. Even more concerning, 59% of those managing small teams receive no training whatsoever. When the success recipe starts with "promote without training," it's no wonder we're experiencing a leadership drought.

It's like promoting a violinist to conductor — technical skill doesn't translate to leadership ability.

Scared Humans in Expensive Clothes

If you're frustrated with your boss, here's the hard truth: they're probably frustrated too. Namaste.

Most bad managers are just scared humans in slightly more expensive clothes. That director who can't make a decision? Drowning in impostor syndrome. That VP who changes direction every week? Feeling pressure you can't see.

The most successful professionals don't just endure difficult managers — they strategically adapt while preserving their own growth trajectory.

The Art of Managing Up

When you start complaining about your manager, you've hit the limits of your own ability to manage up. That frustration isn’t just about their shortcomings — it's the edge of your own influence skills.

But there's good news hidden here. Bad managers, or I might call them "not right for you right now" managers, can be your greatest teachers if you choose to learn from them. And with some strategic adaptation, you can expand that influence. Not in a manipulative way, but in a mutually beneficial partnership that serves you both.

Think of it like learning to cook by watching kitchen disasters: you'll know what to avoid. Every micromanagement moment becomes a masterclass in trust-building. Every poor communication example transforms into a lesson in clarity.

Create Structure Where None Exists

If your manager struggles with organization you can solve it:

• Send agenda suggestions before meetings

• Follow up with action item summaries

• Create tracking systems that make both of you look good

I once had a manager who couldn't remember what we discussed from week to week. Instead of getting frustrated, I started sending brief summaries after our one-on-ones: "Based on our conversation, I'll focus on X, Y, and Z this week. I'll need your input on A by Thursday." Suddenly, we were aligned – not because she changed, but because I filled the gap.

Translate Your Work into Their Language

Bad managers often don't understand what you do, which leads them to either micromanage or disappear entirely. Help them understand:

• Connect your work to metrics they care about

• Translate technical concepts into business outcomes

• Share progress in terms that matter to them

• Ask them what's their preferred way to learn new information

When I worked in product design, my manager cared exclusively about deadlines, not quality. Rather than fight this, I started framing quality issues as schedule risks: "If we rush this design phase, we're likely to face three extra weeks of engineering revisions later." Suddenly, he became an advocate for thoughtful work.

Make Them Look Good (Strategically)

All managers have goals. Help them succeed:

• Identify their priorities (often different from what they say)

• Deliver wins they can showcase

• Anticipate questions from above

This isn't about flattery – it's about aligning incentives. When your work makes them successful, they'll naturally give you more support and freedom.

Create Safe Learning Opportunities

Remember, most bad managers never learned how to manage. Create opportunities to practice:

• Ask for feedback in specific areas

• Invite their input early in processes

• Acknowledge when their guidance helps

One of my most improved managers started changing after I asked him: "When you managed other teams through this situation, what worked well?" This question assumed competence he didn't have yet, but it gave him space to think like a true manager rather than just react.

Adapt or Stagnate

When faced with challenging management, you have a choice: adapt strategically or remain passive.

Without strategic adaptation:

• Your productivity and satisfaction suffer

• Work stress follows you home, affecting relationships and well-being

• Career progress stalls in cycles of frustration

• You focus on survival, not growth

With the approaches we've discussed:

• You create structure that benefits both you and your manager

• You turn challenges into opportunities

• You build influence regardless of organizational limitations

• You develop skills that transfer to future roles

If you lead other managers, your response has a multiplier effect: you shield your managers while modeling adaptability.

Dancing in the Rain: Your Choice Matters

Bad managers are inevitable, but unlike weather, you're not limited to just enduring. Those who thrive aren't luckier — they're deliberate. The strategies above are your professional climate control system.

Here's another uncomfortable truth worth considering: if you plan to lead others someday, you'll almost certainly be someone's bad manager before you become a great one. Research shows that leadership skills develop through experience and reflection, not just intent. Treating today's difficult managers with empathy prepares you for when others will need to manage up with you.

Sometimes a manager is truly toxic. If you're developing unhealthy coping mechanisms or facing ethical concerns, it's time to leave. As research indicates, up to 75% of employees who quit their jobs do so because of their manager, not the company.

Every minute you spend cataloging your manager's failures is a minute you're not spending on building yourself. You can invest your energy in building a case against them, or in building your resilience.

The next time you catch yourself cataloging your manager's failings, pause and ask: "How can I improve my situation?"

Difficult managers are inevitable, but being unprepared for them is a choice. What you do next determines whether you stagnate — or thrive.

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

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For most of my life, I thought writing was for other people: the ones who read voraciously and who kept journals. After all, I spent much of my early career as a designer who thought in sketches and systems, not sentences. But leadership changed that. I struggled to translate my thinking into writing until AI gave me the bridge I didn't know I needed.

As an undergrad at the University of Georgia's Terry College of Business (Goooo Dawgs, sic 'em!), I never had to write long papers. Class was all about case studies, group projects, and presentations so I never built the habit of writing to wrestle with complex ideas.

Over time, I noticed that people who could write clearly were the ones who could think clearly. They could cut through noise, make sense of ambiguity, and bring others along with them. These days, writing is my intellectual home base. But it wasn't always that way.

From Sketches to Sentences

I've always been an intentional communicator but just not through writing.

As a UX designer, I relied on whiteboarding and sketching. Visual thinking let me rapidly iterate on concepts and spot relationships that would have been buried in paragraphs. These drawings evolved from personal thinking tools to powerful ways to collaborate and align teams.

Then leadership changed everything. In one meeting, I sketched out a product roadmap, only to hear: "Can you put that in writing for the executive team?" Suddenly, my go-to tools weren't enough and in some cases, they were frowned upon. Sketching was seen as micromanaging. Stay in your lane, Frank! I had to articulate ideas without leaning on visuals. And if I'm being honest, as someone who isn't an avid reader, I doubted my ability to be an effective writer.

But in a world that runs on documents, writing wasn't optional. What started as a necessary chore became something more: a way to sharpen my thinking, connect with others, and scale my impact. Writing cuts across disciplines and works for designers, product managers, engineers, and sales teams alike. At its best, its clarity is unmatched.

When Writing Forces Honesty

I'm a good bullshitter in meetings where charm and fast talking can gloss over contradictions. Oh, the charisma. But words on a page don't move; they just sit there staring back at you, exposing every logical gap.

If I can write something that feels both true to me and valuable to others, I know I'm onto something. Writing forces clarity in a way that speaking doesn't. The finite nature of putting something down on paper curbs the hand-wavy explanations you can get away with in conversation.

Now, as a product and leadership coach, writing has become one of the most effective ways to communicate what I offer: Here's what you'll get working with me. Just like writing for my team created a reusable artifact that scales beyond one conversation writing as a coach allows me to do the same for the broader industry. That's deeply rewarding.

And that's what led to Frank Takeaways — the newsletter you're reading now and my most sustained writing practice to date.

The Problem Wasn't Writing; It Was Bridging Design Thinking to Writing

For years, I thought my problem with writing was discipline. But then I realized: what if my brain just wasn't wired for traditional writing? What if I needed a different process?

AI completely changed how I understand my own writing process.

When AI writing tools emerged, I didn't think, Finally, I can become a better writer. I thought, Thank god — something to make this torturous process less painful. I approached AI like someone with a toothache approaches Novocaine: not to improve the visit, just to get through it.

What I discovered was surprising.

As a designer, I was used to rapid iteration of sketching, scrapping, and refining ideas visually until patterns emerged. Traditional writing forced me to commit too early in a linear format, interrupting the design thinking flow I relied on. What I needed wasn't better writing skills but a bridge between my visual, iterative thinking process and the written word.

AI didn't dilute my voice but amplified what was already there, making my writing more authentically mine. Before, I spent 70% of my energy on structure and basic phrasing, leaving little room for deeper insights. Now, I can focus almost entirely on the perspectives only I can provide like how design thinking applies to organizational change or the patterns I've noticed in successful (and failed) product launches.

AI applied design thinking principles to writing. The rapid prototyping, iteration, and feedback loops that defined my design process now shaped my writing process too.

How AI Became My Digital Whiteboard

A whiteboard lets me rearrange ideas before the marker dries. AI does the same for writing by keeping my words in pencil, not ink. Here's my actual workflow:

• Organize, Scaffold & Scale Method: AI helps me transform raw thoughts into coherent frameworks. I can brain-dump observations and quickly identify underlying patterns for a newsletter or map connections across multiple newsletters.

• Possibility Explorer: Stuck? I ask AI: "What if decision-making worked like cooking?" Boom. Mise en place as a leadership model.

• Resistance Test: I'll write an initial draft, then ask the AI to challenge my assumptions and identify logical gaps. This process forces me to dig deeper in a judgment-free environment, often revealing insights I hadn't recognized in my own thinking.

The Paradox: More Human Than Human

AI doesn't generate my insights or experiences. It can't tell you about the product launch that failed because we optimized for the wrong metrics, or how I learned to balance confidence with curiosity as a leader. Those lessons come from my lived experience. What AI does is help me package those insights in a way that resonates.

For leaders, this shift is transformative. The math is simple: meetings scale linearly; writing scales exponentially. AI removes the friction that kept us trapped in the limited bandwidth of conversations.

Here's the paradox: AI makes writing more human, not less. It gives me the same fluidity I loved about whiteboarding, letting ideas flow without mechanical friction.

Many leaders remain trapped in the myth that writing isn't worth the effort. If that's you, you're missing your greatest leverage point. AI won't write for you but removes your last excuse not to.

So write. The excuses are gone. Ironically, AI didn't make my writing less human but more me.