In a recent post, I wrote about leadership as a story — and more specifically, as a genre. The kind of culture you’re building, the way people experience working alongside you, the emotional environment you create without always realizing it. All of it adds up to a narrative. And the question worth asking is whether that narrative is the one you’d actually choose.
But there’s a follow-on question that matters just as much, and it’s one most leaders never get around to asking:
How do you know if it’s working?
Deciding what kind of leader you want to be — what genre you’re trying to write — is an important first step. But intention and impact are not the same thing. You can be fully committed to leading a certain way and still be producing a very different experience for the people around you. The gap between what you intend and what people actually experience is almost always invisible from the inside.
This is why assessment isn’t optional. It’s the mechanism that closes that gap.
Here’s how I think about it practically. When you define your leadership story — when you decide, for instance, that you want to build a culture of genuine psychological safety, or creative risk-taking, or honest accountability — you need to get specific about what that actually looks like. Not in the abstract, but in the day-to-day.
What does truth-telling look like in the culture you’re trying to build? How do people engage with conflict? What happens to creativity — is it encouraged, tolerated, or quietly punished when it creates inconvenience? What does performance look like, and are people pushing the envelope or doing the minimum required to stay safe?
Those questions give you a script. And once you have a script, you can assess against it.
Every three to six months, come back and ask: Are my team and I experiencing what I set out to create?
If the answer is yes across the board, you’re in rare company. More often, you’ll find something like this: sixty percent of what you were trying to build is there. The environment feels mostly right. People are engaging as you hoped. But there’s a forty percent gap — something that isn’t landing, something drifting from the culture you intended, something that needs adjustment.
And sometimes people wave off that gap as “fine,” or “yeah, but it’s pretty good,” or “…better than it was,” and they stop pushing for the 100%. To quote Jim Collins: “Good is the enemy of great.” But I would also add that great can be the enemy of done.
Let’s be clear: forty percent is not a failure; it’s not meant to judge. It’s information.
The instinct, when something isn’t working, is often to conclude that the whole approach was wrong — to scrap the genre entirely and start over. But that’s rarely the right move. More often, the story just needs editing. The sixty percent that’s working tells you what’s solid. The forty percent that isn’t tells you where to focus.
So you adjust. You refine. You come back three months later and check again. Did the sixty hold? Did you make progress on any of the forty?
That’s how a culture actually gets built — not through a single bold declaration of intent, but through repeated, honest assessment and the willingness to edit the script.
The leaders I’ve seen build the strongest cultures aren’t the ones who got everything right from the beginning. They’re the ones who kept coming back to ask whether it was working — and who had the courage to adjust when the answer was no.
