I work with founders, business owners, and CEOs for a year at a time. It’s a six-figure investment, and more than half renew.

More than one has called the work “priceless.”

We do a lot less than you’d think.

Every relationship starts with a two-day retreat. I began doing these a few years ago, and frankly, I had no idea what I was doing.

In theory, I got it. Space. Reflection. Room to think.

But instinctively, I started teaching. To add value. Show how clever I was. Prove I was worth the fee.

Over time I saw how wrong that was. And how little I need to do instead.

Here’s what a dozen retreats — 1:1 and group — have taught me.

Your Insight Beats My Information

I can tell you things. Stories, frameworks, methodologies. And I do. But it has humbled me how often a client stops me mid-sentence because they’re chasing something of their own. An insight in the making.

That insight is the whole point. The less I teach, the more room there is for it. More and more, I just point a client back to their own capacity to know.

Sometimes I don’t even have to do that.

The Work is in the Silence

We talk plenty over two days. But we also fall into silence, and I’ve learned to enjoy what can arise there.

I once had a four-hour lunch with a client. Much of it was him staring out the window, shaking his head, chuckling.

“I’m going to have so much more time.”

He’d seen how much he was doing that he didn’t need to do — thinking eight moves ahead when reality wouldn’t warrant one. I didn’t add a thing. I just enjoyed watching him see it. (And that insight was as true for me as it was for him.)

Less is More (And It’s the Hardest Part)

Slowing down is the hardest thing for most founders. They live in maximize mode: doing, fixing, making sure nothing slips. The adrenaline creates a kind of productivity myopia — a constant fear that something will get missed. I can see the withdrawal start when I tell them we’re going to do as little as possible for two days. No agenda. No structure. Yes, we’ll talk. Yes, things will surface. But my one job for those two days is this:

Can I understand my client’s world?

If we can slow down enough to see how they are creating the world, we can see the assumptions, rules, and truths that got them here.

And we can see what’s in the way of whatever’s next.

Want to go deeper?

Unpack more of the how and why in my weekly Substack — https://substack.com/@jeffmunn

“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.