They're Smart, They'll Get There
Why the hardest part of leadership is watching someone take a ride you've already been on
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.