Time to read: 2 minutes

Here’s what I have seen derail more good leaders than bad strategy, poor hiring, or market conditions combined:

An assumption that felt completely reasonable until it wasn't.

Consider this: A CEO I coached was convinced his leadership team was fully aligned around a major initiative. When we looked more closely, each leader had a fundamentally different understanding of the goals, the priorities, and what success even looked like. Nobody was lacking talent. Nobody was lacking effort. They were simply working hard in completely different directions.

Nobody had questioned the assumption. So it quietly became fact.

I wish I could say this was only something I observed as a coach. I made this mistake myself as a CEO more than once.

Most organizational problems don't begin with bad intentions. They begin with assumptions.

The most common ones sound like this:

☐ My team knows exactly what I expect.

☐ If there's a problem, someone will tell me.

☐ Everyone understands our priorities.

☐ We have a solid plan and we are executing it well.

☐ My people have what they need to succeed.

☐ Everyone is on board with this initiative.

☐ We do not need another progress meeting.

☐ My team understands how their work connects to our larger goals.

These assumptions feel true. They feel efficient. They make us feel confident.

But the real question, the harder one, is this:

How do you know?

If you can't answer that with evidence rather than instinct, you may be leading on assumptions rather than facts.

The leaders who get into the most trouble are rarely the ones who don't care. They're the ones who stop verifying and start assuming.

The most effective leaders I've worked with do something different. They keep checking. They ask questions. They seek feedback. They verify alignment. They challenge their own thinking, even when everything appears to be running smoothly.

That's the work I enjoy most: helping leaders uncover assumptions they didn't realize they were making before they become costly mistakes.

Here's what I'd like you to consider:

Looking at your organization today, which of these assumptions are you least certain is actually true?

Hit reply and tell me. I read every response personally. Sometimes that one conversation changes everything.

‍