In my previous post I wrote to a senior IC who was thinking about leaving. In this post, I’m writing to the person sitting on the other side of that conversation: the new manager.
You were a brilliant IC eighteen months ago. Now you have a team, a roadmap that won’t stop shifting, and leadership that can’t seem to decide what matters this quarter. You’re under real pressure, and I’m not going to pretend otherwise.
Most first-time managers are handed the role and almost none of the tools.
But here’s the thing about pressure: it flows downhill unless someone stops it. And right now, your most experienced person is sitting across from you wondering whether it’s time to go.
In that earlier post, the IC with fifteen years of experience had written in after a rough conversation with their manager left them contemplating a transfer or an exit. I wrote about what the IC should think through.
This post is for the manager: the one who maybe had the best of intentions, spent two hours in that room, and still walked out having handed the problem back to their report.
I know that manager well. Sixteen years ago, it was me.
The month that changed how I manage
When I started managing my own team, I was excited. This was my chance to be the manager I’d never had. A few people were now looking to me for guidance and motivation.
Six months in, I was in over my head. All I could feel was the pressure from above: pressure to build, pressure to ship, and pressure to prove I was a leader (I could handle this new responsibility, this promotion).
My response was to make my team work Saturdays.
That lasted until the Saturday came that I was too tired to work, and they were too tired to push back. I looked around the room and said, “Y’all can go home.”
I kept trying to hold it together by holding on tighter until a direct report told me, in a 1:1, that they were leaving. That’s when it landed: I was in over my head.
I had two options. I could say “OK,” let them walk out, and never think about it again. Replacing someone is brutal, though, especially someone who’d shown they cared. So instead I asked questions. I even asked the hard one: “Was it something I said or did?”
I must have built enough trust, because they said yes.
I paused and waited.
They told me there’d been a lot of drama between me and someone else at the company. While I was busy sorting that out, I’d stopped really checking in. Sure I was still running 1:1s, but for the sake of having them. My attention was all on delivering to customers. And the people building the product? Somehow they hadn’t made the list.
So I made one more ask: “Give me a month to turn this around.”
I spent that month listening. Not working more hours, not bringing back Saturdays: just listening and processing. And once I understood the problem from their side, I didn’t try to fix it alone. I asked for help. A trusted advisor shadowed me and showed me my blind spots.
Here’s what they taught me.
The verdict that should have been yours, not theirs
It started with a line I’ve never forgotten: if a two-hour 1:1 ends with “you need to figure things out,” the meeting failed and it’s on the manager, not the report.
What actually happened in that room
A senior IC came to you with a concern. Probably something like: “We’re navigating too much change too fast, and I can’t tell what we’re optimizing for.”
Start by giving them the benefit of the doubt: that sentence isn’t a complaint. It’s your best early-warning system, handing you data for free.
If you treat it as a complaint: “You’re not performing at a senior level, you need to figure things out”, because you feel like you have to hold a high bar, all you’ve actually said is: you disappointed me, try harder next time.
But how? More hours? More experiments? It’s unclear. All you did was pass your own ambiguity straight to the person least able to resolve it. They can’t set priorities. They can’t make leadership decide. You’re asking them to fix the thing that’s now your job.
That’s the shift nobody warns you about. As an IC, your value was having the answers. As a manager, your value is creating the conditions where your team can find them. Telling a senior person to “figure it out” isn’t delegation. When the ambiguity is organizational, it’s abdication.
What to do instead:
- Name the ambiguity out loud. You don’t have to fake certainty you don’t have. “Leadership hasn’t landed on priorities yet, and I know that’s making this hard — here’s what I’m doing to get clarity” is infinitely stronger than pretending the chaos is a performance problem. Senior people can handle uncertainty. What they can’t handle is being told it’s their fault.
- Be a filter, not a funnel. Your job is to absorb the noise from above and pass down a smaller, clearer set of priorities. If everything that lands on you lands on them unprocessed, you’re not managing, you’re forwarding. “Ignore three of those five things this week; here’s the one that matters” is worth more than any roadmap. And if you can’t name which three to drop, that’s your signal to go get answers from leadership or help from someone more experienced.
- Treat concerns as signals, not insubordination. Under pressure, the instinct is to read pushback as a performance issue. Resist it. Your strongest people are usually the first to name what’s broken, precisely because they care enough to say it. Punish that once and they’ll stop telling you, right up until they tell you they’re transferring.
- Protect their breathing room. Catch the small issue before it becomes a five-alarm fire. And before you ask someone to work a long weekend, ask yourself whether it’s truly necessary or just your own anxiety looking for an outlet. Breathing room isn’t a perk; it’s the condition under which good work happens.
- Ask what support looks like. End the hard conversation with a different question than the one you opened with. Not: “Can you perform at a higher level?” but: “What’s in your way, and what can I move?” You’ll learn more in five minutes than in the previous two hours.
The part you won’t see coming
High performers rarely make a scene. They don’t escalate, they don’t issue ultimatums. They quietly explore an internal transfer and you find out when the farewell invite hits your calendar. By then the meeting that failed is months behind you, and you’ve probably forgotten it. They haven’t.
You can always tell leadership the person was a mis-hire that they couldn’t rise to the challenge. Maybe that’s even true.
But ask yourself what happens in another six or twelve months, when the next person feels the same way. Or when the rest of the team stops leaving and starts quietly checking out instead, dropping the ball because it’s safer than caring.
And ask what you’ll say when a candidate looks you in the eye and asks, “Why did the last person leave?” Or, “What does it take to get promoted here?”
You can always find someone more desperate, someone who just wants the job. But are they the one who’ll tell you when something’s on fire? Or will they just say “yes,” and get back to work?
And here’s the part that takes the longest to see coming: none of this stops you right away. You can manage like this for years, a decade, even, and keep climbing. Senior manager. Director. Beyond. You delivered, and you delivered at your team’s expense, and for a long time that’s exactly what the company rewarded.
But it catches up. Maybe it’s the manager who quietly built a team people fight to join, taking the promotion you assumed was yours. Maybe it’s the day someone finally names the attrition on your team out loud. Or maybe it’s just luck running out: you stayed because it was comfortable, the cuts came, and now you’re standing in front of every skeleton you locked in that closet, wondering who’s left to vouch for you.
The good news: the same role that lets you push pressure down also lets you stop it. That’s the whole job, really. Not having every answer, but being the person who turns chaos into something your team can stand on.
Your senior IC brought you a problem worth solving. The only question is whether you’ll treat it as theirs to figure out, or yours.
I told you how my story started, not how it ended.
After that month, my direct report didn’t leave. They could see I’d actually heard them, they even patted me on the back for it, and that was enough. It meant more to me than any promotion or paycheck, because of what I finally understood in that moment about how trust and loyalty actually get built: not through hours or heroics, but through courage. The courage to admit when I’d failed, and the courage to ask for help when I needed it.
Where to start this week
You don’t fix culture in a quarter. But you can change the next conversation. A few concrete moves:
- Reopen the meeting that failed. Go back to that report and say, plainly, “I don’t think I handled our last conversation well. Can we try again?” Naming it does more than any perfectly run 1:1.
- Pick the one priority. Before your next team meeting, force yourself to name the single thing that matters most this week, and say out loud what people can drop. If you can’t, that’s your homework with leadership, not theirs.
- Find your trusted advisor. I didn’t fix my team alone, and you won’t either. Find one person: a peer manager, a mentor, your own manager to shadow you or pressure-test your blind spots.
- Ask the better question. In your next 1:1 with a senior IC, replace “How’s it going?” with “What’s in your way, and what can I move?” Then sit in silence until they answer.
Pressure will always flow downhill. The only question is whether you’re the floor it lands on, or the filter that turns it into something your team can actually build on.
Have you ever caught yourself passing pressure down instead of absorbing it, and what finally helped you stop? And if you’re a new manager staring at a conversation you’re not sure how to have, send me a message. I’ve been on both sides of that room.
I write about the conversations no one trains you for from one side of that room or the other. My last post was for the IC thinking about leaving. This one was for their manager. Subscribe to my newsletter and you’ll get the next one before you need it.
