Many business owners we’ve spoken with didn’t start with a huge team on day one. They had to learn how to be a good boss, but the problem is the books on leadership are often highly theoretical and so we wanted to hear practical examples of what it means to be a good boss. So, we asked some brilliant, insightful folks to share stories about the best bosses they’ve had.

Kyle Olson

Who’s the best boss I’ve ever had? I’ve had some good ones – but Matt Hensley takes the cake. He’s someone who truly gets it. Maybe it’s because we both hail from Wisconsin, but it felt like we were on the same wavelength right from the start, sharing values that made us a great team. Read more>>

Lonny Stormo

When I started my first full-time medtech job, I found that Jim, two levels above me, was one of the most respected and feared leaders in the company. As I moved up in the company, I eventually reported directly to Jim. One day I asked him how he was so able to be a visionary to know what direction we should go. Read more>>

Raelyn Stuart

The first job I had straight out of undergraduate college was as an administrative clerk in a branch of government. I was often applauded for my hard work by my boss at the time and always felt valued as an employee, like the work I was doing mattered. One day, about a year into my job, my boss asked me to meet with him privately. Read more>>

Jeff Lambson

The best boss I ever had was Olga Viso. She was director at the Smithsonian Institution’s Hirshhorn Museum and Sculpture Garden, the nation’s museum for modern and contemporary art in Washington, DC. I was fresh out of grad school and working as a temp in the museum library, filing books and helping curators with research. Read more>>

Hanna Waters

I currently have what I’d consider to be the Best Boss Ever. I’m an artist, which means I work a full-time job outside of my creative practice. I’m just under a year into a totally new kind of 9-5 – corporate B2B sales – a position wherein I would have crashed and burned were it not for my mentor and Sales Manager, Jon. I never wanted to be in sales, when sales often and immediately conjures up visions of used car salesmen working carlots like sharks; however, financial insecurity and curiosity will thrust even the most unlikely souls into the proverbial ring. Read more>>

Nadean Carson

I was deployed to Iraq as part of Operation Iraqi Freedom/Operation Enduring Freedom as an Air Force Captain in 2004. I worked in the Multi-National Security Transition Command – Iraq as part of the Civil Engineering (J7) team. We were charged with rebuilding the Iraqi Armed Forces bases across the country. To say it was the biggest job of my life is an understatement. Read more>>