Why Smart Leaders Keep Doing the Thing That Stopped Working

I had a conversation recently - a CEO I respect, genuinely sharp, building something real - and about forty minutes in she said something I've been thinking about since.

"I know this isn't working anymore. I can feel it. I just don't know what to do instead."

And the thing is, she did know. She'd known for a while. She just kept reaching for the familiar thing, the thing that worked before, because the alternative required admitting that the version of the company she'd built the first answer for didn't exist anymore.

This is not a failure of intelligence. I want to be really clear about that. This is one of the more human things I see in leadership work, and it happens to the sharpest people I know. When something has worked - genuinely worked, carried you through hard seasons, earned trust, built culture - it accumulates a kind of authority. You don't just let go of it because the conditions shifted. You try it again. And again. And when it keeps not quite working, you try harder.

The tug of the familiar is physics. It's not weakness.

But here's the thing that actually helps: you don't need to know what the new thing is before you can acknowledge that the old thing has run out of road. Those are two separate steps, and confusing them is where a lot of smart leaders get stuck. They hold onto the familiar because the alternative feels like a void. But naming what isn't working anymore - out loud, with honesty, to the people around you - creates space. And space is where the next thing gets built.

Late spring is a surprisingly good time for this. Something about the season - things growing fast, old structures becoming visible - makes it easier to see what's been propped up versus what's genuinely load-bearing.

What's still on your list because it used to work?

Want to name where this is showing up in your team? Start with a short Fourfold diagnostic, then use the result to choose the right next step.

Hard work matters.