There is a question I don’t hear asked enough in leadership conversations: How willing are you to look a little ridiculous? Now, I didn’t say reckless or unprofessional. Just human.
I have cooked burgers in a chef’s hat at an employee lunch. I have participated in a dance-off during the Hava Nagila at a staff party. And I was fully prepared to don a pair of Mickey ears during my recent trip to Disney World if my granddaughter had asked me to.
None of those moments were beneath me. They were some of the most important things I have ever done as a leader (or grandfather, for that matter).
Here’s why: When the person at the top of an organization is willing to set aside their own dignity for the sake of a moment, it sends a signal to everyone watching. It says: This is a place where you do not have to be perfect—where you can laugh, be yourself, and belong. That’s no small thing; it’s a culture in the making.
Now consider the opposite. We have all worked for someone who never loosened up, never laughed at themself, never let the mask slip even for a moment. Maybe they thought it projected strength. What it actually projected was distance, and distance is expensive.
It shows up in teams that do not speak up, in employees who do not bring their best ideas forward, and in cultures where people feel like they are performing for their boss rather than working alongside them.
A recent Harvard Business Review study further drives the point home. When senior leaders fail to model openness about their own imperfections, middle managers begin to assume that perfection is the price of survival.
That’s no small thing; it’s a culture in the making.
That assumption ripples downward. Teams stop speaking up, problems go undiagnosed, and the whole system quietly stiffens. As the researchers emphasize, empowerment is hollow without psychological safety. And psychological safety starts at the top.
Sabrina Baker, founder of Acacia HR Solutions, frames the solution well. In a people-first environment, she says, leaders understand that by focusing on employees first, the innovation, efficiency, and productivity will follow. That starts with relationship. And team relationships rarely begin in the boardroom. They begin in the moments when a leader steps out of the corner office and stands shoulder to shoulder with the people they serve.
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The leaders who build the most loyal teams are rarely the ones who command the most respect from a distance. They are the ones who close the distance entirely.
So, here is a practical challenge: This week, find one low-stakes moment to let your guard down. Volunteer for something a little awkward. Stay for the part of the event where things get informal. Laugh at yourself before anyone else gets the chance. It does not have to be a grand gesture. It just has to be genuine.
Your team members are watching. And what they are hoping to see is that you are one of them.
