Real Trust Isn’t Built in 1:1s

I learned early on in my career that the best way to get honest answers out of people was to have open conversations in untraditional environments.

In the truck while driving to run a quick errand, walking to grab a quick coffee at lunch, or that five-minute window before a meeting started—when the “real talk” slipped out just long enough to matter.

Environments where the stakes feel lower.

Where no one is trying to sound impressive and self-preservation hadn’t kicked in yet.

See, most workplace environments don’t invite honesty.

They demand performance... and sometimes, compliance.

But when the setting feels informal, human, and low-pressure, people start telling you the truth.

Not just about the work. About how it feels to do the work.

What’s broken, what gets ignored, and all the little things driving them up the wall.

The kind of information you need as a leader to make clear, high-quality decisions.

But most people skip over this step entirely.

Which is why when they step into a new role or take on a new project... they blow it.

They come in hot —full of ideas, ready to improve things, fix things, optimize things.

Yet rarely do they have the full picture of what they’re actually "optimizing for."

So instead of observing, they start adjusting.

Instead of asking questions, they start making changes.

And when you change things without understanding how they actually work, you don’t look decisive. You look arrogant.

To the team, it doesn’t matter how good your intentions are. It only matters that you skipped the part where trust is earned.

Nobody likes to admit this, because doing so requires facing our own inadequacies. But:

Most people in the workplace don’t have a history of competent leadership.

They have a backlog of bad decisions made by people who never asked enough questions.

So when someone new steps in with confidence and no context? They don't get excited, they brace for impact.

If you’re stepping into a new team, a new project, or even just a new layer of responsibility—start here:

Assume no one trusts you yet.

Not because you’ve done anything wrong, but because you haven’t earned the right to be believed.

Operate like the person before you left a mess—and everyone’s still cleaning it up.

Because most of the time, they’re not looking for someone with answers.

They’re looking for someone who gives a damn enough to ask better questions.

Slow down and be present with them.

Ask if it’s cool to ride along.

Get them to show you how they do things—with no agenda and no pitch.

Sit in the room. Attend the meetings.

Stack chairs after the event and ask what part of the day dragged.

Because you're never going to learn the truth in a survey.

You're going to learn it while someone’s taking out the trash.

And as much as we’d all like to shortcut trust to get to the outcome faster… we can’t.

So remember:

1.) You can’t diagnose from a distance.

2.) You earn the right to lead by getting close enough to understand.

3.) People open up when they forget you're the one in charge

If you want people to follow your lead, show them you’ve done the work to understand theirs.