Oh No

Five to ten times a quarter, the sky falls. Then, it doesn't

I had too many 1:1s on my calendar last Friday. By the time my team member said the word “news,” I had already said “oh no.”

He’s on my exec team. The kind of person you build a quarter around. The kind of person who makes you confident enough to say yes to harder problems because you know the bench can handle it.

He was telling me he’s moving on.

First thing through my head: not now. Not this quarter.

It takes a year to build that kind of bench. You don’t replace it in a quarter.

By Friday afternoon, I’d called one person I trusted to be clear-eyed about it. By Friday evening, I’d read the board in — calmly, with what I knew, what could be impacted, what I was already doing about it.

It took me two days to get over it. I was glad it landed on a Friday.

Most of that work happened inside my own head. Running disaster movies — the team noticing he’s gone, the next person leaving, customers feeling the gap. Recalculating the quarter. Replaying the last three months for the signal I missed. The conversation I should’ve had. The check-in I postponed.

By Wednesday next week — three business days later — I was genuinely excited for him.

You want your loyal people to dream big. You want the ambitious ones to take the bigger seat when it shows up. You can’t keep them forever and you shouldn’t want to. But when the moment lands — when the words show up in your ear or in your inbox — none of that helps. And the world feels like it’s crumbling.

A few weeks earlier, a different kind of email showed up — from one of our top customers. A driver of real growth, with real opportunity ahead.

Here’s the line that landed hardest:

“I want to be very clear — I am extremely frustrated with our experience as customers... another very serious concern.”

I read it twice. Then a third time. Then I started running the math. Five percent of revenue was at risk if I didn’t handle this cleanly. A relationship we’d spent years building, in jeopardy in three paragraphs. Discontent had been brewing under the surface for months — small things, missed signals, basics not done consistently. My point person was on vacation. And the hot potato landed in my lap.

This one took weeks, not days.

I had to acknowledge it without flinching. Look at my own gaps in oversight before I asked anyone else to look at theirs. Hold my team accountable for higher quality without turning it into blame. Do the basics consistently — calls returned on time, commitments tracked, small things stacked. Basics we’d taken for granted because the relationship was strong. Sky was falling. Until it wasn’t.

Today the relationship is mended. Far from perfect. But it’s back.

Both weeks had the same shape.

The gut runs disaster movies. The damage almost never matches the trailer. Not because the threat isn’t real — sometimes it is. But because the brain calculates worst-case in five seconds, and the actual outcome takes weeks of real work to reveal. By the time it does, you’ve usually already moved the dial.

Here’s what nobody tells you when you take the seat: this job puts you in five to ten of these situations every quarter. They are not the exception. They are the work.

Each one is a rep. You only get the rep if you stop running from the feeling.

So now, when the words land, I have a sequence I trust.

Tell one person who’ll be clear-eyed about it. Not to vent. To stay sharp.

Tell the board the same way every time: here’s what happened, here’s what could be impacted, here’s what I’m already doing about it, here’s what I need from you, here’s when we’ll talk next. Five lines. No drama.

Map the blast radius — this quarter and this fiscal year. Then find the smallest workable next step. Take it.

Make sure the person on the other side of it feels respected and supported. Relationships outlast the crisis if I let them.

And give myself a weekend to feel it. If I can.

I used to think the CEO job was not feeling the swings. Hold your face. Show up calm. Be the unflappable one in the room.

Now I think it’s the opposite. The job is feeling them faster. Gut punch. Recalibrate. Act. Shrink the time between the three.

From months, to days, to sometimes hours.

You don’t get to skip the “oh no.”

You only get to practice making it shorter.