“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—