The Conversation You’re Avoiding
Is Costing You Everything
You know exactly who came to mind.
I’ve been coaching business owners for 25 years across the Midwest, and I can tell you the single most expensive problem in a growing company isn’t cash flow, isn’t marketing, isn’t your tech stack.
It’s the person sitting in a leadership seat who shouldn’t be there anymore.
You know exactly who I’m talking about. You thought of them before you finished that sentence.
They Were Right — Once
Here’s what makes this so brutal. That person was probably the RIGHT hire at one point. Maybe they were your third employee. Maybe they built your sales team from nothing. Maybe they held things together during the year you almost didn’t make it.
And now your company has outgrown them.
The job they were hired for doesn’t exist anymore. The job that exists now — managing 40 people, building systems, thinking strategically about a $25 million operation — that’s a different job. And they’re drowning in it. You can see it. Their team can see it. The only person who can’t see it, or won’t, is you.
Because you feel like you owe them.
What It’s Actually Costing You
Let me tell you what I’ve watched happen — not once, not ten times, but hundreds of times across Ohio, Indiana, Michigan, Illinois, Minnesota, and Wisconsin.
A CEO keeps someone in a leadership role 18 months too long out of loyalty. During those 18 months:
Their best people leave. Top performers don’t quit companies. They quit leaders who can’t keep up. That director who can’t run a team of 30? Their three best people are already interviewing. You won’t find out until the resignation letters hit your desk the same month.
Decisions don’t get made. The wrong leader in the wrong seat creates a decision vacuum. Things that should take a week take a quarter. Opportunities pass. Competitors move. Your team learns that “waiting for approval” is actually code for “it’s not going to happen.”
Culture rots from the middle. Your values are on the wall. But culture isn’t what’s on the wall — it’s what gets tolerated. When the rest of your team sees that underperformance at the leadership level has no consequences, they recalibrate. The standard you walk past is the standard you accept.
You stop growing. Not because the market isn’t there. Not because you don’t have the capital. Because your organizational capacity is capped by your weakest leader. I’ve watched companies flatline at $15 million for three years because the CEO wouldn’t make one change.
The Lie You’re Telling Yourself
“They’ll figure it out.”
“I just need to give them more support.”
“I’ll hire someone underneath them to shore up the gaps.”
I’ve heard every version of this. You know what I’ve never heard? “I waited two extra years to make the change and I’m so glad I did.”
Every single CEO I’ve worked with who finally made the move said the same thing:
“I wish I’d done it sooner.”
Every. Single. One.
This Isn’t About Being Ruthless
I need to say this clearly because I think it’s why so many leaders avoid this conversation. Making a change doesn’t mean you’re ungrateful. It doesn’t mean those years of loyalty didn’t matter. It doesn’t mean that person is a bad person.
It means your company has evolved, the role has evolved, and the fit has changed. That’s not betrayal — that’s business growing the way it should.
Keeping someone in a role they can’t succeed in isn’t loyalty. It’s cruelty. They know they’re struggling. They go home stressed. They’ve lost confidence. Letting them stay in a seat where they fail slowly isn’t protecting them — it’s protecting you from a hard conversation.
The most loyal thing you can do is be honest.
Getting the Right People On Is Just as Hard
In Columbus right now, the talent war is real. Intel, JPMorgan, Nationwide, the healthcare systems — they’re all competing for the same leadership talent, and they’ve got deeper pockets than you do.
So how does a $20 million company attract a leader who could go work for a Fortune 500?
Mission. The right leader for your company doesn’t want to be a cog in a machine. They want to build something. They want impact they can see. They want a seat at a table where their voice changes the direction of the company. That’s what you offer that Cardinal Health can’t.
Speed. In your company, a great leader can make a decision on Tuesday and see results by Friday. In a Fortune 500, that same decision takes two quarters and four committees. The right people are attracted to velocity.
Ownership. Not equity necessarily — though that helps. I mean psychological ownership. “This is MY team, MY P&L, MY problem to solve.” The best leaders are drawn to that like oxygen.
You can’t attract the right people if the seat is already occupied by someone who isn’t performing.
The right people won’t come if they can see, from the outside, that you tolerate mediocrity in leadership.
Your reputation in the market matters. Word travels fast in Columbus.
The Sequence Matters
In 25 years of coaching, I’ve learned that the order of operations matters more than most people think.
Wrong order: Hire the new person, then figure out what to do with the old one. This creates confusion, resentment, and political drama that poisons your culture for months.
Right order: Have the honest conversation first. Make the transition with dignity and respect. Create clarity about what the role needs now. THEN go find the person who fits.
The gap in between? That’s where you grow as a leader. Sitting with the discomfort of an empty seat is better than filling it with the wrong person. Every time.
One Conversation
Here’s what I want you to take from this.
You don’t have a strategy problem. You don’t have a market problem. You probably don’t even have a product problem.
You have one conversation you’ve been avoiding. And on the other side of that conversation is the company you’ve been trying to build.
Twenty-five years. Six states. Hundreds of companies. The pattern never changes.
The right people in the right seats changes everything. And it starts with the conversation you already know you need to have.
Are You a Hero or a Performer?
The same loyalty trap that keeps the wrong person in the seat keeps you performing instead of leading. Find out which loop you’re running.
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Get the Book — Name Your PriceIf somebody came to mind while you were reading this — the leader you’re protecting, the team that’s suffering, the conversation you keep postponing — send this to them. That’s how change travels.