I was in a coaching session this week with a CEO I've been working with for a while. He runs a fast-growing marketplace, just expanded into a new country, and is in the middle of closing a round.

By every external measure, things are going well. By every internal measure, he is exhausted.

We were talking about his co-founder, the COO, who runs operations and has been carrying a lot of the people-management weight on the team. There were a few hires that weren't working out, and this CEO could tell that his co-founder was avoiding the hard conversations.

The problem was, the CEO didn’t know how to support the COO.

"I don't want to insert myself," he told me. "It's not really my domain. I trust him."

My reply was, "Yeah, but trust isn't the same as empowerment. Have you actually told him that?"

This CEO had been treating his hands-off stance as respect. But his co-founder was almost certainly reading it as absence.

That's when I told him the story I'm about to tell you. It's the story I tell almost every CEO I work with at some point, and it's the single most important reframe I've ever absorbed about what the job actually is.

A long time ago, when I was working as Chief of Staff and later COO, my boss said something to me that I genuinely did not understand the first time I heard it.

I had asked him something fairly tactical, probably about how he worked with the CEOs he coached. And he said, "Regina, you have to know a secret about coaching."

I said, "Okay, what is it?"

He leaned in, and said, "Every great CEO eventually becomes a coach themselves."

I kind of squinted at him. "What do you mean? They come to us for coaching."

He said, "Yes, but they come to us for coaching ... so that eventually, we coach them how to be good coaches to the rest of their team."

I remember thinking that sounded like a tongue twister and not a real insight. So he kept going.

My boss explained that the CEO sits in the most elevated position in the company, no matter how flat the org chart looks on paper or how much you insist that "we're all just teammates here."

Whether someone is a co-founder, a director, an early IC, or your tenth employee, they are wired (and I do mean evolutionarily wired) to look to you for approval.

As a CEO, your reactions are weighted differently than anyone else's.

Your silence is interpreted. Your absence is interpreted. Everyone searches for your praise, and when you withhold it, it is noticeable.

So even when a CEO tries to stay out of someone else's domain, they are always present in their team’s minds as THE person whose buy-in they're seeking.

The job, then, isn't to insert your opinion into every decision they're making.

The job is to coach them through their decisions - the same way a coach would - by asking the questions that help them see what they already know.

That conversation with my boss was years ago, but I still think about it almost every week.

What this looks like in practice

Back to my client this week.

After I told him the story I just shared with you, I gave him the version I think every CEO needs to hear.

Your job, with your co-founder, is not to take over people management. It's to coach him through it.

Here's roughly what that sounds like in real life:

The next time he sits down with his co-founder and asks how things are going on the people side, his co-founder will probably do that thing many of us do. He'll shrug and say, "Same old."

That kind of answer is the avoidance, and is not the real answer, so you have to keep going.

The CEO's job in that moment is to gently push. "Can you elaborate? What's actually been on your mind there?"

The co-founder finally names the thing. Let's say, for example, it's a hire who isn't working out.

The CEO’s first instinct is going to be to either fix it for him or to commiserate.

Both are wrong.

The coaching move is to ask, "What do you want to do about it?"

His co-founder will probably hedge. "Well, I think we need to let her go. But I feel really bad. She's a good person, she works hard, the team likes her."

And here's where most well-meaning founders blow it:

They start workshopping the decision.
They ask whether he's sure.
They suggest a PIP.
They start debating the merits.

When you engage in that kind of behavior, what you are actually doing is trying to rescue someone from the discomfort of the decision they need to make.

The coaching response is much shorter, and much harder to actually deliver.

It's something like, "Okay, set the pain of doing it aside for a second. Just the decision itself, separate from the implementation. What's the right call?"

He'll say, "We need to let her go."

Your job is to reply, "Then go forth and do it. How can I best support you?"

That’s it. Be the sounding board and the coach to your team.

The Playbook on Growing as a CEO

None of these moves are dramatic. None of them require you to take anything off your plate or theirs.

What they require is that you stop being the doer and start being the person who empowers the doers around you.

The cost of not making the shift

What I've watched happen to founders who don't make this shift is that the cost compounds slowly, and most of them don't notice until things are already bad.

When the CEO stays in doer mode, the team learns to wait.

They wait for the CEO to weigh in before they decide.
They wait for the CEO to fix the hire that isn't working.
They wait for the CEO to have the hard conversation.
The org slows down at exactly the speed at which the CEO is the bottleneck.

Worse yet, the people who are supposed to be the senior leaders in your company never actually get to operate as senior leaders.

They become very expensive executors of the CEO's preferences.

And the truly good senior leaders eventually leave, because being a senior leader who isn't allowed to lead is one of the most demoralizing roles in any company.

It's also, I think, the part of the CEO role that almost nobody warns you about.

You spend your early years as a founder building everything yourself, and then one day someone has to tell you that the muscle that got you here is now the muscle that's holding you back.

I'll leave you with the question I asked my client at the end of our session:

Diagnose it, then go be a coach instead of a doer.

Until next time,

Was this newsletter forwarded to you? Are you here for the first time? If so, remember to subscribe below…