“This is the last straw.”

A CEO client said that to me last week about one of his most senior people.

I’d heard versions of the story before. High-stakes meeting. A fair question from a colleague. And his senior guy turned it personal, blows up the room, and walks out.

Not the first time. Not the second.

So I asked: “You already know where this is headed. Why are you resisting calling it now?”

Long pause.

“It’s probably kindness.”

His care is real. Years of history, genuine contributions, and a man going through a heavy personal burden in addition to work.

But here’s what else was true. Even in the meetings where nothing went wrong, the room was braced. Everyone is half-waiting for the next eruption. The honest conversations his leadership team needed weren’t happening.

The kindness wasn’t protecting anyone. It was taxing them — including the man himself, exhausted from trying not to be who he’d been for most of his adult life.

Your Work to Do

Here’s what I see with every founder I work with:

The thing you most need to work on keeps showing up. Different people, different years. Same problem.

It’s not bad luck. Long before you founded a company, you picked a way to be safe in the world. Control. Competence. Being the responsible one. Being good.

That first pick built everything.

Some of us picked twice. Two guiding principles.

The decisions that sit on your desk for months are the ones that force your two picks to fight.

My client’s first pick: be right. Twenty years as the trusted number two to the founder. The advisor who never got it wrong.

His second: be kind. Be better to others than his father was to him. Give people their shot at redemption.

The Decisions That Sit

A firing splits those down the middle. Being right says end it. Being kind says one more chance. Neither can win without betraying the other. So the decision sat. For years.

“If your old boss handed you this exact situation and asked for a recommendation — what would you tell him?”

He laughed.

As the analyst, he’d have answered in thirty seconds.

The conflict was actually false. He can be right AND kind. Clear about where it ends, generous about how — severance, time, a dignified exit on the man’s own terms.

The only casualty is the version of kindness that never delivers hard news. That version was never protecting the man. It was protecting my client’s picture of himself as the kind one.

Delay isn’t kindness. It’s just the slowest way to deliver the same news.

Sometimes There is Another Way

I talked to my client again yesterday. We talked in earnest about the part of him that wanted to be done, and the part of him that wanted to make it work.

“What I want is for you to be able to do either of these things, a firing or a path forward, comfortably. If you think firing a long term hire will make you a bad person, this identity will limit you as you build the company beyond the one your predecessor built.”

He surprised me with his next step. The person we have been talking about is great at many things. He is loved by his team. He is valuable in many ways.

He just blows up in meetings with his peers.

So my client changed his role. He is no longer on the leadership team, but still in charge of the people who will do anything for him.

My client knows it might not work. But he is willing to try.

What About You?

What was your first pick?

And if you made two — what decision is sitting on your desk right now, forcing them to fight?

Is there a way through both of those aspects?

Or better yet, to see their impact on you and make the best choice regardless?

Going Deeper

If you want to go deeper on this and other leadership topics for founders and CEOs, I write every week on Substack. Including diving deeper on the topics I write on here.

Here’s the link to take a look—

https://jeffmunn.substack.com

One of the hardest things for my founder clients to do, at least as we start working together, is take a break.

My clients have teams. They have people who can, for some period of time, run the company without the founder.

And yet, at least at first, the founder resists this idea.

“I want them to know I’m there for them.”

What they won’t say out loud:

I need them to need me.

No. You need them NOT to need you.

Your company isn’t worth anything until it doesn’t need you.

Until you can go away, for a month, or a year, and come back to everything as good or better than it was before.

We’re in the middle of the summer. Some founders proudly say they are taking time off, while staring at their phones in the middle of family outings and muttering things like “this will only take a second.”

Don’t get confused between what your business needs and what you need.

Take the time off.

The Fourth of July is a great time to test this out.

See who needs who.

Does the business need you, or do you need the business?

Is your business really a business if it can’t survive without you?

It took two heart attacks before Mike would consider that the problem might be him.

He runs one of the most successful construction companies on the West Coast. Strong, tattooed, always in motion. The guy who solves everything.

That was the problem.

Because he solved everything, his people brought him everything. He’d replace their good ideas with his better ones, then wonder why they stopped thinking. He’d trained them to need him — and then resented that they did.

He grew up in a neighborhood full of crime and drugs, and learned to control everything around him to stay safe. That control built his company. Now giving it up terrified him.

It was the one thing he needed to do.

I invited him to Denver for two unstructured days. No agenda. He kept asking for one. I kept shrugging.

People expect me to push, to fix, to hand them a tool. I don’t. Mostly I get quiet. And I wait.

We didn’t talk about strategy or solutions. We just stopped rushing. And in the quiet, what was in the way stopped hiding.

It was him.

I didn’t tell him that. I didn’t have to. Sure, I might have poked and prodded a bit. But mostly I stayed quiet long enough for him to see it himself — the thing that had been true the whole time.

And then he began to see other possibilities.

Leaving the office for a month. New locations without living on the road. Actually being in a conversation with his wife instead of somewhere else in his head.

A bigger company. And less work.

He left lighter. Happier.

And fidgeting just a little bit less.

Sometimes what you most need to see only shows up the moment you stop looking for it.

Only one thing. You.

I was having coffee with a friend, a nonprofit executive director who felt stuck.

He came to me with a list of things that he wants to do—adding programs, adding locations, increasing the impact of the incredible work that he has been doing with youth in our valley.

I asked him what was the first thing he needed to do.

“I need to raise enough money to add some paid positions.”

I live near Aspen. It’s a fascinating combination of people who struggle with the insanely high cost of living, and a small number of people who have multigenerational wealth.

The small number of truly wealthy people support a lot of good causes.

My friend has one of those causes. People love him and the work that he does. But he has always had trouble raising enough money.

“I have some issues with money,” he confided.

Tell me more.

“There is so much money in this valley that I think, at a certain level, it’s vulgar.”

I looked at him.

“So you think money is vulgar. Do you wonder why you have trouble raising it?”

Oh. He laughed. And then I saw his eyes well up. This wasn’t about him. He was just the messenger for a bigger mission. And his beliefs—that he was an artist, that he should struggle, that the people who had money were bad and greedy and even vulgar—were getting in the way of him fulfilling that mission.

Hundreds of kids in our valley are counting on him to let go of all that.

What Would Be Fun?

There’s usually a way around your rules. A fun way to get to the same place.

“I’m not very good at asking people for money.”

“What if you didn’t have to?”

This week my friend is reaching out to parents whose kids have gone through his programs. He has worked with some of them for several years. I asked him to collect stories. To ask how his work with them has impacted both the child and the parents.

“You don’t think some of those people are going to ask how they can help you? Or offer to introduce you to other people who want to help you?”

His eyes welled up again. “That’s a conversation I would love to have.”

Do the thing you love doing. Everything flows from that.

The Cage You Have Built

Every person I have worked with has had at least one major “rule” that they thought was true but was really just made up. And when we identified it and let go of it, everything changed.

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