If you're in charge of people, projects, or profit, this one's for you.
One of the biggest blind spots I see in leadership is assuming we know why something worked or didn't. We chalk it up to timing, pricing, or "they just weren't ready." But the truth is, many people are guessing.
And as leaders, guessing isn't good enough.
You're not selling a product—you're selling clarity
A few days ago, I referred one of my clients to a family member who needed work done. The client submitted a bid, and I followed up to see how it went.
It turns out he didn't get the job—not because the price was too high, but because it seemed too low. The family member didn't understand what was included, didn't feel confident in the process, and went with someone else who charged more but explained things better.
That's what stuck with me.
The job wasn't lost on numbers. It was lost on trust, on clarity, and on what wasn't said.
There are only two reasons you lose
After 15 years of doing this work, I've found that most losses boil down to one of two things:
- You did or said something you shouldn't have.
- You didn't do or say something you should have.
You didn't ask the next question.
You skipped over explaining the value.
You assumed the expectations were clear.
Or you assumed the client understood what "good" looked like.
You won't spot these patterns if you're not reviewing your wins and losses. And if you don't spot them, you can't fix them.
Debriefing is a leadership behavior
I don't just teach salespeople to debrief—I teach leaders.
That means asking after every project, client, or hire:
- What did we do well?
- Where did we lose alignment?
- What would we do differently next time?
This isn't about blame—it's about growth.
Your team is watching how you evaluate outcomes. If you're not curious, they won't be either. But if you normalize the conversation, improvement becomes part of the culture.
The best leaders I know don't just celebrate wins or avoid losses. They slow down and ask why. And that one habit changes everything.
