What Three Bad Bosses & One Great Boss Taught Me About Leadership

I've been a student of leadership for over five decades. I learn every day from leaders - but my foundational learning came from four gentlemen.

I spent fifteen years in non-profit management. I had some good bosses, some OK bosses, one great boss, and three really lousy bosses.

One of my lousy bosses made grand promises – to staff members, to volunteers, to customers. Yet, he kept few of his commitments. I learned his word was not trustworthy.

Another lousy boss was skilled at pointing out my mistakes and failures. Yet, he was quiet when I exceeded expectations and moved the organization forward. I learned to insulate myself from his presence because all I heard from him was disappointment.

My worst boss asked me to lie. My branch team and I worked our butts off to raise $25,000, which was double what they had ever raised before. But at the campaign’s closing dinner, with 300 people in attendance, my boss told me to get up in front of everyone and tell them we had raised, not $25,000, but $30,000. I refused, and announced the real total. He wasn’t happy. I didn’t care – and left that job as quickly as I could.

Again, I’ve had a handful of good bosses – but it took one gret boss to really open my eyes to the power of inspiring leadership and a values-based culture. I met Jerry Nutter early in my non-profit management experience while he was facilitating a week-long career development session.

During that week, he held us to high standards, praised our progress, and called us on our crap. He set up clear ground rules for how we’d work together and he held us accountable. I felt supported and inspired. I couldn’t wait to get to each morning’s session.

At the end of that week I told Jerry, "I am going to work for you someday."

He replied, "Thanks for the warning, kid!" We both laughed - and knew it would come to fruition.

It took me a couple of years to find a job working for him, but it was worth the wait. Being on Jerry’s team, day in and day out, was exactly like the experience in that week long program. I loved coming to work.

Eventually, Jerry handed me the project of a lifetime. He wanted me to take the ideas he used to build his team culture, and teach them to the non-profits in the country’s roughest neighborhoods.

I built a team of talented, committed leaders across the US. We crafted teen programs built upon character and values. We took these concepts to branches all over the country, including inner city branches, places with heavy teen gang influences. It was our job to make these non-profits a compelling enough place so that teens would leave the gang life.

Our program offered what teenagers wanted then and now: a sense of belonging, cool activities, and meaningful contribution. Gangs serve the same needs. We were crafting a service-based life built on these needs.

Slowly, our ideas for creating a service culture based on clear values started taking hold. Branches began seeing teenagers return to their programs and buildings. Some of those kids became camp counselors, bus drivers, and camp directors. Others became branch program directors and even executives.

Jerry, my best boss, taught me how powerful culture is, driving performance and values-alignment. I was so transformed by my experiences with Jerry that I wanted to expand those ideas out as far as I could. I knew that if having a more values-aligned culture could turn around gang members, perhaps it could work in our workplaces.

Twenty-five years ago I started teaching these same principles in corporations, helping leaders to serve kindly and helping organizations be inspiring places to work. What have your lousy bosses and great bosses taught you about leadership and culture?