The Conversations You're Not Having Are Costing You Millions
Every PE-backed business I walked into as an operating partner had the same first job waiting for me. Not strategy. Not financial engineering. Not the value creation plan.
Conversations.
The ones the founder had been putting off. Sometimes for months. Usually for years.
The VP of Sales who’d been coasting since the business hit $8M. The co-founder who hadn’t grown with the role but owned 30% of the equity. The pricing model everyone knew was leaving money on the table but nobody wanted to take to the client base. The senior hire who was loyal, committed, well-liked by the team, and wrong for the next stage of the business.
These weren’t mysteries. Everyone in the building knew. The founder knew. They’d lost sleep over it. Rehearsed the conversation in the shower. Probably a dozen times.
And then Monday arrived, and they didn’t have it. Again.
This is the most expensive leadership habit in scaling businesses. Not bad strategy. Not weak execution. Conflict avoidance. It almost never gets named for what it is, because from the inside it doesn’t feel like avoidance. It feels like patience. Loyalty. Picking your battles.
It’s none of those things.
Every Conversation You Don't Have Is a Decision You've Already Made
Every conversation you avoid is a decision by default. You just haven’t admitted it yet.
When you don’t address the underperformer, you’ve decided to carry the cost for another quarter. When you don’t move on pricing, you’ve decided margin compression is acceptable. When you don’t confront the leadership misalignment, you’ve decided that working around it is a better use of everyone’s time than resolving it.
You would never make those decisions deliberately. But you’re making them every week the conversation doesn’t happen.
And the cost compounds. A performance issue that takes a direct conversation and a 90-day plan to resolve in Q1 becomes a restructuring exercise by Q4. By then the team has reorganised itself around the problem, built workarounds, and in most cases quietly given up on the idea that leadership deals with things like this.
I saw this play out in a business I was brought into post-acquisition. The founder was sharp. Commercially excellent. But there was a senior leader who hadn’t been right for the role in at least two years. Everyone knew. When I asked about it in my first week, the answer was: “Yes, I know. I’m handling it.”
He wasn’t handling it. He was accommodating it. And the real cost wasn’t that person’s underperformance. It was the three good people underneath them who had stopped pushing because they’d concluded, reasonably, that this is a business where problems like this don’t get dealt with.
That’s the compound cost of conflict avoidance. Not the conversation you haven’t had. The message your avoidance sends to every person who’s watching.
The Loyalty Trap
The skills that build a business from nothing are relational. You hire people who believe in you personally. You build loyalty, trust, shared history. Your early team took a bet on you when nobody else would. That creates a bond that feels like something you owe them.
So when someone who was right at $2M is visibly wrong at $15M, having that conversation doesn’t feel like leadership. It feels like betrayal. You wait. You hope they’ll grow into it. You give them another quarter. You tell yourself you’re being fair.
You’re not being fair. You’re prioritising your own comfort over their future and the business’s value.
The fair thing is to tell someone the truth early enough that they can do something about it. The founder who waits two years and then finally acts hasn’t been patient. They’ve been unkind slowly while calling it loyalty.
What a Buyer Sees
When a PE firm interviews your leadership team during due diligence, they’re not just assessing capability. They’re reading the room for unresolved tension. The things that haven’t been said. The dynamics everyone has learned to step around.
It shows up in how your team talks about each other. In the careful pauses when certain names come up. In the gap between what the org chart says and how decisions actually get made.
A leadership team with unresolved conflict is a signal that the founder either can’t see the problem or can’t act on it. Neither is good for your multiple.
One of the most reliable indicators I used to assess a business pre-close was simple: ask the founder what their hardest people decision was in the last twelve months. If they have a real answer, with some discomfort in the telling, that’s a business run by someone who confronts reality. If the answer is vague, or too smooth, or doesn’t exist at all, there’s a drawer full of conversations that haven’t happened. And I know I’ll be the one having them after close.
The Reframe
The conversation you’re avoiding isn’t neutral. It has a cost. It shows up in your EBITDA, your team’s performance, your culture, and eventually your multiple. Every week it goes unhad, you’re not being patient. You’re choosing the current state. And the current state is getting more expensive to change. Put it this way: it’s much easier to kill the monster when it’s small.
The founders who build valuable businesses aren’t the ones who avoid hard conversations. They’re the ones who have them early enough that they never become the kind of entrenched, structural problems a buyer has to price around.
As you read this today, you already know which conversation this is about. You’ve known for a while.
And the thing that stops most founders isn’t information. You don’t need another framework. You know what needs to be said. What stops you is doing it alone, without someone in your corner who’s had this exact conversation dozens of times before and knows what happens next.
If that’s where you are right now, reply to this email with the word CONVERSATION. We’ll set up a call to talk through where you are and what the next move looks like.
And if you know a founder sitting on a conversation they keep putting off, forward this to them. Sometimes the nudge must come from outside.
What’s Next?
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