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.

Christy Cater

The best boss I’ve ever had is my body. Having Type 1 Diabetes since I was not quite two years old has given me the greatest lessons of my lifetime. Growing up with Diabetes was really hard. My relationship with food was torturous. Insulin, the hormone my body does not make, was developing but not flexible. There were no insulin pumps and once the insulin was delivered via syringe injections, it was active in my body. Read more>>

Bianca Willis

My favorite boss is my current boss, Joe Valeri. One, I don’t have to feel like I have a boss that I have to report to every day. He allows me to freely do my job and make important decisions and if I slack he will let me know. Two, he has pushed, supported, and educated me in ways that most people would have to pay for. He owns the wine shop (V-NO Fells Point) and I run the day-to operations. When Drake says “started from the bottom now we here” I instantly think of my relationship with him. Read more>>

Chelsea Adinuba

The best boss I’ve ever had was myself. This isn’t the typical answer you would expect when someone asks you a question such as this one. I am here to encourage you all: nobody knows you better than you know yourself. You know when it is time to apply pressure, and when it is time to take a break. You know your needs, your wants, and your schedule better than anyone else does. When I was 16 years old, Read more>>

Rob Carty and Guy Nunnellee

Rob Carty: Since we’re a duo, it’s only fair to nominate the one boss who both of us worked for: the great Audrey Baker. Technically, she’s also the worst, but she was so good that we’ll suspend that unfortunate quirk of logic and just label her as the best—especially since we were such terrible employees. This has nothing to do with music, though. Read more>>

Kalia McKinley

Leadership Means Meeting Team Members Where They’re At. I sat in on a weekly meeting while my boss instructed my other colleagues and me about various assignments. I wrote as fast as I could, but I was not familiar with the project and he was talking fast. When I got back to my desk, I was told he needed two other projects before the one he had just assigned. Read more>>

Jennifer Cox

The retail shop, Make.Do., is one of a couple of businesses I run, but this one is the business that gives me the most back. I had always been trained through high school, college and graduate school to be a high-performer, rewarded for hard work. That turned into me thinking I had to always do the most often at the expense of my physical and mental health. My last year of grad school, I had a fabulous mentor/colleague while working at PBS in Alexandria, VA in the General Counsel’s office. Read more>>

Idriss Al’ Rashad

I have had a few but the most influential was my immediate boss while serving in the U.S. Navy, First Class Petty Officer Christopher Larrison. He was well decorated and highly regarded by his superiors. I admired his decisive leadership which was perfect for the job function in a very stressful and chaotic environment. This was important to me because life comes with many surprises and decisions that must be made on short notice; decisions that can influence the trajectory of your life. I recall his independence from political ideologies allowed him to view things objectively. Read more>>