What’s Our Strategy? Are the Three Most Frustrating Words in Leadership

Why when you're tired of saying something, it's when others hear it for the first time

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 still feel that pit in my stomach when someone asks: "What's our strategy?" After years in leadership, you'd think I'd be immune to it. But I'm not alone – I've watched countless other leaders have the same reaction. Their shoulders slump (just like mine), their energy drains (just like mine), and everything screeches to a halt—it's the corporate equivalent of a record scratch in their symphony. The question stings twice: either there's an unknown strategy (painful) or there isn't one (soul-crushing). I've lived both scenarios.

Have you ever played an album so many times it feels less like music and more like a conversation? Each lyric resonates so deeply that you can't tell if it's speaking to you or through you. Mastery can feel the same way—until you realize others are hearing it for the first time.

Around the hundredth listen, you move from hearing the notes to anticipating them. The once-invisible threads connecting the choruses to the bridges reveal themselves. The album stops feeling like someone else’s story and starts to feel like one you know.

What's interesting is when someone else listens to the same album for the first time, and they don't hear what you hear? It's frustrating. How can they not hear what's so clear? How can they not feel what's second nature to you?

This is the paradox of mastery. The deeper you sink into understanding, the harder it becomes to see the starting line—or to remember hearing it for the first time.

The Paradox of Mastery

Experts often struggle to teach their skills to others. Psychologists call this the "curse of knowledge"—though "curse of expertise" might be more accurate. Like a musician who can't remember learning their first chord progression, we forget that our intuitive leaps are built on years of small steps.

This disconnect affects knowledge sharing in organizations. Experienced leaders often forget that their understanding of the company's direction comes from deep involvement. While the direction may seem obvious to them, their teams need time to process and internalize what leadership sees as self-evident. But just like that well-worn album, what's second nature to you is uncharted territory for them—your team is hearing the music for the first time.

Rolling out a new feature seems straightforward to you. You've spent months connecting the dots, refining the vision, and tying it to the bigger picture. But to your team, it's like hearing the first track of an album: interesting but unfamiliar. They don't see the callbacks or the overarching story.

Reconnecting With Your First Listen

Here's the truth: it's not hard to explain a complex idea. What's hard is remembering what it's like to hear it for the first time. That intricate web of connections in your mind wasn't built in a day. Just like you needed repeated album listens to catch the subtle callbacks and thematic threads, your team needs time and repetition to build their understanding.

The magic lies in creating space for discovery. Remember how the tenth listen of your favorite track revealed different layers than the first? The same principle applies to complex ideas. What feels like redundancy to you might be someone else's aha moment.

How to Help Others Hear the Music

If you're tired of explaining, here's how to help your team move from their first listen to their hundredth:

Let the Track Play

Create space for discovery, just as you once had. No one falls in love with an album by reading its review. They need to experience it, let it play in the background until a line hits different, a melody clicks, a pattern emerges.

Example: Instead of presenting a fully-baked strategy, share an early draft. Let your team experience the rough cuts, B-sides, and refinement process. Their questions and confusions aren't interruptions – they're part of the remix.

Share Your Liner Notes

Remember those album booklets revealing each song's story? Every great album has its origin story – the late-night studio sessions, happy accidents, and creative dead ends that led to breakthroughs. Your strategy needs the same documentation of its evolution. It's not just about the final mix, but all the versions that didn't make the cut.

Example: When rolling out a new product direction, one leader created a "strategy diary" documenting decisions, dead ends, and pivots. It became the team's strategic songbook.

Create Space for Their Interpretation

Sometimes the best way to help others connect is to stop conducting. As Miles Davis famously said, music lives in the spaces between notes – understanding works the same way. When team members share their interpretations, resist the urge to correct or redirect. Their journey through understanding is as valid as yours.

Example: In my last strategy session, I caught myself about to explain every pattern I saw. Instead, I bit my tongue and asked, "What patterns are you noticing?" The silence was uncomfortable, but the insights that followed were better than anything I could have prescribed. They found hooks and bridges I hadn't even considered.

Find the Rhythm Together

Great bands don't just play at each other – they play together. They create a safe environment to experiment, miss a note, or suggest a different arrangement. Your team needs the same psychological safety to engage with the strategy, not just nod along. Create regular moments to sync up, share interpretations, and build collective understanding.

A Note on Tempo

Let me acknowledge a reality I face every quarter: sometimes we need to ship now, decide quickly, or roll out changes before everyone's fully on board. Creating space for discovery isn't always possible – and that's okay. You can apply these principles in parallel with your decision-making process, or after key decisions. The goal isn't to slow progress but to deepen understanding over time. You'll listen to a lot of music and have other opportunities.

Think of it like releasing singles before an album drops. Sometimes you need to get the hit song out while the full artistic vision is still developing. The key is recognizing that understanding can grow alongside – or after – your first take.

Closing Thoughts: When the Music Isn't the Problem

Here's a hard truth I learned: Sometimes when someone says they can't hear the music, they're too polite to say they hate the song.

When your team says "We don't understand the strategy" or "What's our direction?"—consider another possibility: they might understand it perfectly well but just don't agree with it. This isn't about clarity—it's about conviction.

Just as Conway observed that organizations design systems mirroring their communication structure, teams interpret strategy through their local context. Sometimes what sounds like confusion is their reality clashing with yours. Think about genres you don't enjoy. You can recognize a well-composed jazz piece or technically impressive metal solo without wanting it on your playlist. Similarly, your team might grasp your strategy perfectly while harboring reservations about its direction.

Understanding isn't always the barrier—sometimes it's alignment, motivation, or trust. Some resist because they don't see how the strategy serves their goals. Others might understand the notes but disagree with the arrangement. These aren't comprehension gaps; they're conviction gaps.

Next time you're frustrated with endless strategy questions, pause. Are you hearing "I don't understand," or "I'm not sold"? The difference matters.

Mastery isn't just knowing the music; it's creating space for others to connect to it. Sometimes, it's being open to the possibility that they hear it just fine – they're just not ready to dance.

I need to put an album on repeat. I'd tell you which one, but you wouldn't understand—yet.