The Stories Leaders Tell Themselves

Most leaders I talk to genuinely want to hear disagreement early. They mean it. They're not performing openness. They've seen what happens when concerns arrive too late, and they don't want that again.

So they say it. My door is open. Push back. Tell me if something isn't working.

And then they wait.

What often comes back is quiet. Or general agreement. Or concerns that surface three weeks after the decision is made.

And almost immediately, a story forms.

It's easy to read the silence as disengagement, or fear, or a team that doesn't care enough to speak up. But most of the time, that story isn't the whole picture.

People are making a calculation. A quiet one. And it's rooted in something much older than this team, this leader, or this organization.

Many people were shaped in environments where disagreement was earned, not offered freely. You listened first. You waited until you were certain. You raised concerns privately, and only once you'd established enough credibility to be heard without being dismissed.

Speaking up too early wasn't bold, it was presumptuous.

Others came up in workplaces where raising concerns early was the signal that you cared. You tested ideas before they hardened. You pushed back as a form of engagement, not defiance. Staying quiet was what felt risky.

Neither of those histories is wrong. They're just different lessons, learned in different rooms, about when disagreement is welcome and what it says about you when you offer it.

The stories form quietly, on both sides of the table.

When someone speaks up early, a leader might tell themselves: this person is being difficult, impatient, not quite ready. Or they might tell themselves: this person is engaged, invested, someone worth listening to.

When someone stays quiet, that same leader might tell themselves: we're aligned, people trust the direction. Or: no one cares, this team is checked out.

Four very different stories. All of them feeling like observation. None of them checked for accuracy. 

What makes it easy to miss is that nobody names it. The person who waited didn't explain why they waited. The person who pushed back early didn't say they were trying to help. The leader didn't say out loud what they were reading into either response. Everyone moved forward carrying their own narrative, and the gap stayed invisible.

That's usually where things start to fray. Not in one big moment, but in the quiet accumulation of stories that never got questioned.

So before asking why people aren't speaking up sooner, it's worth pausing on this: what story am I telling myself right now about what I'm seeing? And is that story actually mine, or did I inherit it somewhere along the way?

That's usually where the real work begins.