I Wanted to Be the Cool Boss — and Almost Destroyed My Organization

When I took the reins of a new nonprofit startup, I knew exactly what I didn’t want to be.

I’d spent my career in healthcare organizations that felt oppressive and cold, filled with rigid policies, punitive management, and an overwhelming sense of hierarchy. I told myself I would do it differently. I would create a place where smart, passionate people could thrive without micromanagement or red tape.

In hindsight, what I created wasn’t healthy. It was chaos.

The Vision That Went Wrong

I rejected structure in every form. Policies? Unnecessary. Oversight? Stifling. Direction? People didn’t need it — I believed they would instinctively do what was right.

I often said, “We’re just a bunch of cool cats doing healthcare.” I envisioned a team of like-minded peers who loved the mission and loved working with me.

In reality, I was driven by ego. I wanted to be the boss everyone loved. I blurred professional lines, treated staff like friends, and sought validation in their approval.

When they didn’t behave the way I wanted, I got angry. Worse, I became unpredictable and unprofessional — drinking too much at work events, crossing boundaries, and failing to uphold the standards I thought I stood for.

Perception Is Reality

To me, I wasn’t a tyrant. I wasn’t oppressive or authoritarian. But none of that mattered. What mattered was how my staff experienced me — and they saw me as autocratic and unsupportive. That disconnect between my self-image and their reality shook me. Still, I was slow to change.

Without clear leadership, toxic behaviors took root. I had unknowingly normalized dysfunction.

The breaking point came when a public scandal — one I was directly involved in — nearly destroyed the organization. We lost the trust of funders, local officials, peers, staff, and the community we served. I could no longer pretend the problem was external. The problem was me.

The Hardest Lesson of All

What followed was the most difficult leadership work of my life. I had to dismantle the version of myself I had clung to and accept that being “cool” was never the job.

I replaced ego with humility and began building structure and accountability. Clear policies, defined expectations, and healthy boundaries became non-negotiable.

I also had to get real with myself and look at the staff who could grow and those who needed to go. If I had been part of the problem, could I authentically let other “problem” staff go?

I realized the best path forward was to be upfront and honest. I shared openly: “This is what I’m learning about myself, and this is where we’re going.” Some people accepted it, some assumed it was just words, and some didn’t care at all.

I gave everyone the chance to join the new paradigm. Those who refused — some of whom I had once considered friends — had to move on.

Rebuilding trust didn’t happen overnight. I had to show — over time — that I was different. That the organization was different. Staff had to feel empowered within clear guardrails. The culture had to become inclusive and mission-focused, not driven by personality or favoritism.

Slowly, it worked. Turnover decreased. Performance improved. Our reputation recovered. The organization — and I — emerged healthier, more resilient, and aligned with our true mission.

In fact, about four years (this was not a speedy process) into the rebuild, an independent consultant found 100% of staff members scored themselves 5-out-of-5 in feeling like their work was aligned with the organization’s mission and vision, with an equal amount scoring themselves a 4 or 5 on role satisfaction.

What I Want Other CEOs to Know

Looking back, this wasn’t about being “bad” or “good” at leadership. It was about understanding that intent does not matter more than impact.

In development work, we educate our nonprofit leaders to focus on program impact rather than on activities. I’ve never heard anyone say the same should be said for leadership. Leadership without structure is not freedom — it’s neglect. Wanting to be liked is not the same as building trust. Boundaries aren’t oppressive — they create safety and clarity.

If you’re leading an organization, it’s worth asking: In what ways might your ego be getting in the way of your leadership? If you’ve never paused to reflect on this, there’s a good chance there is work to do somewhere.

Are you avoiding structure because it feels restrictive? Are you blurring professional lines in the name of being relatable? Are you excusing impact because your intentions were good? These are tough questions — but essential ones.

These were painful questions for me, but answering them saved my organization. They might save yours, too.

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