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