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.

Karen Braveheart

I’ve been fortunate to have a varied career- as an attorney, a real estate broker, college professor, and entrepreneur. My biggest teacher and mentor is life itself because I learned so much by just getting out there and taking action toward my career and dreams. As I look back on my career, there are three mentors that have positively impacted me. 1) First, was the managing attorney at Travelers Insurance in New York who when interviewing me- challenged me more than any other interview I ever had. He believed in me as a trial attorney. Read more>>

Amber Rainey

Although I would refer to her as “boss” when in her presence, she was the best mentor I ever had. What she taught me, as a mentor, has stuck with me since that day. She taught me about perspective. I am always going to be biased about topics that align with my interests, values, or morals. However, it is important to listen to the perspective of others and see where they are coming from. One person’s perspective doesn’t make the other person’s perspective wrong or invalid. I learned this as a 20-year-old freshman in college working at a retail store. But learning this information has shaped me into the person I am today. It got me promoted twice in two years, and in my endeavors following my departure from that job. Thank you, Chauna, for teaching me the importance of perspective. Read more>>

Lindsay Gallegly

This is a tough question because I have been lucky enough to have several amazing employers before I became an entrepreneur. So top 3 because they all deserve to be mentioned: 1) John Kennedy, Pizza Al’s (Morgantown, WV) 2) Paul Reitano, Rocky’s Pizza (former owner) 3) Cepeda & Landrus Lewis, Growing Tree Chiropractic (Mooresville, NC) But in my journey to entrepreneurship, Paul had the biggest impact. I went to work at Rocky’s Pizza when I was 24 years old. I had already had one big girl job but was switching gears after deciding I wanted to pursue opening a café. I had no idea how to do that and decided working at a locally owned restaurant was a fine place to start, plus I loved pizza. So it felt like a win-win. Read more>>

Katherine Shark

I graduated art school in 2020, which was obviously a difficult time. For about a year after graduating, I was living at home with my parents, working coffeeshop and retail jobs to make my loan payments. I was depressed & unhappy. On a chance, I got a job at a local sewing studio, Needles Studio, owned by Erika. My mom knew her & recommended that I reach out to her, and she offered me a job teaching sewing lessons & helping watch the shop.
That job changed my life – it was the first job that felt meaningful to me, & I was so happy to be doing something related to what I loved. Erika was kind, funny, and most of all transparent – she talked to me about what she charged & why, what her advice was in navigating the industry, and realistic input on what it took to make ends meet in a creative field. Read more>>

Sharday Plair

At a time when I had the best boss ever I would have to spilt between two individuals. The most recent boss I’ve had taught me never to give up and to have confidence in my decisions. He also taught me the importance of having a strong team behind you and also that by becoming a boss, everyone is not your friend. You can’t be timid and you can have everyone like you because people will take advantage. When I received a promotion in a company a few years ago I can admit transitioning from worker bee to supervisor was completely different. People that didn’t think of me as a competitor or even smart had to second think that which caused friction therefore I had to learn how to be more of a leader. Read more>>

Nela Steric

A Tribute to Carole: A Wise and Unwavering Boss and Friend’s Influence on My Life Wise. Unwavering. Loving. Mother. Patriotic. Patient. Persistent. Stubborn. Carole was all these things and more. She was a source of strength and comfort; I will never forget her. Her influence on my professional and personal life was profound, and I am forever grateful for her friendship. She was a second mother to me and many others, although a VERY STRICT second mother, a for-life department chairperson, trusted friend, advisor, counselor, critic… Read more>>

Joanne Docherty

I’m really lucky to have worked for and been mentored by some fantastic people but the one who has had the most impact on me is a wonderful woman called Lorna Trainer. I came back to Glasgow, my home in 2019 after 12 years working internationally. It was such a big move as I had been away for so long. I had the opportunity to work for Lorna’s company L&G Learning doing training that I hadn’t done before as well as gaining a new qualification. Lorna immediately made me feel so welcome, so included and so valued. The team she had created had such a family feel and I settled so easily. I had been worried about how I would adjust after being abroad for so long but I really thrived. I found Lorna exceptionally inspirational – the way that she conducted business in a values-driven way, the way that she treated people. Read more>>

Cheyanne Witter

While I was in college I had the pleasure of being taught and mentored by many amazing artists and professors in various creative fields. Through my whole four years, though, two of these people stuck out the most to me as great leaders. One was a teacher in the Visual Studies department of my school, and the other was my boss at my Studio Monitor position in our Photography studios. Both of these beautiful women were funny, passionate, and very open and honest about their feelings and opinions but not in a way that was ever rude or overbearing. They both were always willing to share their wealth of knowledge with anybody and gave great advice about the art industry. They’re power houses in their respectful departments and integral parts of the continual function of that school. Read more>>