The Most Expensive Sentence in Business

The most expensive sentence in business is “we already know what the problem is.”

I’ve spent my career sitting beside senior leaders at the moment they've named their problem and are ready to spend real money solving it. The pattern I keep seeing is that the problem a leader names is rarely the problem that's actually costing them.

"We need a reorg." Often the real issue is that the CEO hasn't decided what the company should become, and structure is standing in for a decision that hasn't been made.

"My leadership team isn't aligned." Frequently they're perfectly aligned on the facts. What they lack is enough trust to say out loud what they actually think.

"I'm spending all my time managing my team's gaps." Sometimes it's a staffing problem. More often it's the slow cost of people decisions we made for good reasons, where the price didn't show up until much later.

None of this means leaders are wrong. It means the first version of a problem is a symptom wearing a costume. My job is to take the costume off before anyone spends a year and a budget solving the wrong thing.

So before I let anyone, including myself, agree on the problem, I ask three questions.

What is actually happening? The observable facts, stripped of interpretation. Not "the team is resistant," but what was specifically said, done, or not done.

What is underneath it? The incentives, fears, and power dynamics driving the behavior. Almost always where the real problem lives, and almost never where the conversation starts.

What conversation are we avoiding? In my experience, the most useful question a leadership team can sit with, and the one they're least likely to ask.

Which brings me to what I'm working through right now. Most organizations don't fail at their hard problems. They fail at the easy ones no one ever closed.

Someone gets hired or promoted with a gap we can already see. We make the call for good reasons, with their success in mind, and we tell ourselves we'll find the time to coach them through it.

And for a while, we do. At first the gap is manageable, even energizing, something to mentor someone past. But coaching takes time and money no one has to spare, so it slips. The workaround that was supposed to be temporary quietly becomes permanent. It's only a year or two later, exhausted, that you realize the gap never closed. It got absorbed.

And absorbed gaps roll uphill, landing on whoever can least afford to drop the ball: the most senior, most expensive people in the building. The CEO ends up doing his job and a slice of someone else's. So does the person beside him. The highest-leverage people in the company are now spending their scarcest capacity on the cheapest-to-fix problems on the org chart.

That is what overfunctioning actually is. Not a personality quirk or a control problem, but the visible symptom of a coaching deficit that rolled to the top. And it carries a cost no one prices: while the senior team absorbs gaps, the work only they can do goes undone.

I'm still testing where this holds and where it breaks. But I've stopped believing the answer was ever more time, or more people.

What are you doing right now that isn't your job? And what deficit, somewhere below you, is the reason you're doing it?

Hit reply and tell me. I read every one.