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.

Carol Lipworth

Long before starting my jewelry business, I left a secure corporate training job to work as a consultant. My boss had served in the military and had worked in Human Resources when he created an entire consulting business inside one of the U.S.’s largest banks. After working for him for a couple of years, the bank merged with another bank and the department was dissolved. During my stint with this group, I learned what an exceptional leader should be. He was very strategic in hiring his staff; he did his due diligence and while you had to have the skills and know-how to do the work. Read more>>

Danny Jelaca

The best boss I ever had was a Johanna Stella. It was my first job in miami 25 years ago. She was a great mentor and motivated me to achieve my dreams. She had business savvy and great talent and she was celebrity driven and brought Madison Avenue to South Beach. I still run my salon departmentalized and give the highest level of customer service and talent to all the clients and treat them all like celebrities!. Read more>>

Abby Joy

The greatest boss I have ever had is Scott Michaels, which Scott Michaels Entertainment. Scott is nothing but a great leader. Intelligent, caring, empathetic and simply a bad a$$ at what he does. He is patient when he is teaching, and holds a high standard of work ethic and talent. Scott empowers the people who work for him, and I couldn’t ask for a better mentor. From meeting Scott in October of 2019, my life has shifted gears completely. Not only is he an amazing boss and leader, but also a wonderful friend. Read more>>

Tiara Deahn Thornton

The best boss I ever had was Steve Liddell. We met when I was working as a bank teller at Wells Fargo in Las Cruces, New Mexico. He was one of my frequent customers and he gradually learned about my educational background. He was shocked that I had a Master’s degree in Business Administration and working at the bank. I was still deciding what my next career move would be, when he offered me to interview as his Office Manager for a beverage distribution center. Read more>>

Shondrea Fincher

Owner / CEO Golden Gate Funeral Home Dallas, Ft. Worth, and Louisiana “Mr. B.” has been my Mentor for about 5 years. I’ve been an Employee over 10 years, but I didn’t have the mentality to receive what he was trying to pour into my life. I was packed with potential, but the lack of self discipline prevented me from reaching my full potential. He doesn’t just have us to come into work. He trains us for an hour, 6 days a week, as he pays US to become better. Does your Boss do that? :) I’m always shocked at all of the barriers that I’ve been able to knock down under his leadership. He continued to tell me that “you don’t have to be a product of your environment. Let people guess where you’re from, instead of you showing them where you’re from.” Read more>>

Barby Ingle

The best boss I ever had was a director of marketing at a collegiate athletic department where I was a head spirit program coach. She worked with me, was kind, showed patience, gave me room to make choices and mistakes. But the one think that still sticks with me over 20 years later was her reminder that I have choice to make something a problem, issue or challenge. A problem is hard to overcome and most people give up, and issue is an usually responded to emotionally instead of with facts and purpose. A challenge we all want to take on and win. How we face the situation in front of us is a choice. There is always a way to accomplish any challenge. It might be hard, it might take time, but it can be changed. Read more>>

Phillip Fiuza Lima

“Keep punching!!” That is what Mr. Pearson always tells me after our talks. The best boss, yes! Perfect? No! But who is? At first he was my boss then became my mentor, but till today I consider him a good friend and we stay in touch since 2006 after I made the worse decision to leave his company. That was my 3rd and last regret in life. The first two were giving up on going to the Naval Academy and working for the State Department. However, everything happens for a reason and if I did those first two things I would have never met him. Read more>>

Sarah Jackson

Here’s the list of Bosses in my life: 1. Lists. I love them. 2. My family. Love them, too! 3. Friends. 4. Family. (Good things sometimes come in Twos.) 5. My belief that God is still Good. The word BOSS holds power. But that’s not what I want to be known for. The best people in my life have shown me kindness, love, and welcome. No matter what. I’d that that’s a pretty good boss, right?! Read more>>

Holly Gotfredson

I was grateful to have had several wonderful “bosses” over the years who inspired and influenced my leadership style in a positive way. One in particular really stands out – she taught me many things, but one of the most important lessons was to lead humbly and empower your team. She gave me the opportunity to grow- learning much more than just what I was hired to do and gave me the freedom to pitch new ideas, try different marketing campaigns, and invest in new skill sets and personal growth. I never had the mindset that I was “working FOR someone,” but rather was working WITH someone and that really stuck with me. Read more>>

Megan & Christa Reeves

I have had the pleasure of not only working for my mother, Dr. Christa Reeves, as an intern, but as a fellow audiologist. She is the reason I’m an audiologist today and the reason I was able to start my own practice right out of school. She bravely entered the private practice world on her own over 7 years ago and I admire the grit it took for her to get to where she is today. She started out on her own and now she owns a highly successful practice that is becoming more well-known across the state and throughout the audiology world today. Read more>>

Cary Matthews

I’ve been fortunate to have a number of great bosses and managers in my career along with a few that weren’t ones that I would want to emulate. My career grew the most as an operations professional and leader working for Joseph Ciotti. He took a risk on me as a young manager moving to a new industry. He allowed me to learn and make mistakes, and when I did, he was able to balance giving me guidance with supporting me. As I gained experience, he entrusted more responsibility to me and let me take a larger role in running the business. Read more>>

Crystal Jones

You know what’s interesting? Every time I hear about how men have better treatment, better pay, and better opportunities at work I’m honestly a little confused (and crazy grateful) because this has never been my experience. Or rather, it’s not something I’ve ever let hold me back from advancing. When I think about all my past jobs, I can clearly remember every single boss I’ve ever had. I remember the good stuff and the bad stuff that went with each. But what I remember most is the fact that 90% of them were women, and I’ve learned something valuable from almost all of them. Read more>>

Alison Altrui

The best boss I ever had was working in a health food store in 2013-2016. I had worked retail most of my life, then after 6 years I got fired. I had also gotten in a car wreck recently, too. Needless to say I came to my interview, which my friend had set up for me, not in the best headspace and depressed. I was honest in my interview, he knew I got fired the day before, but he gave me a chance and I got the job. I stayed there for 3 years and loved almost every minute. I have always been shy. This was a new job, a new type of work and I had zero idea what I was doing. I exercised but didn’t know much beyond the simple classes I had taken. Read more>>

Carol Bender

My favorite boss, Michael Spraggins, was a high-energy, unconventional, successful, results-driven entrepreneur in the building industry in Florida. He led me and the founding members of LifeNet International with zeal and a business mindset to make a difference in the poorest countries in the world: sub-Saharan Africa. He taught me the invaluable lesson of building a strengths-based team, where each member learns what they’re naturally best at and works in those strengths, and delegates their weaknesses to someone else (who is strong in those areas). Read more>>

Jen Allen

My current boss has had such a positive impact on my career and life. I have been working for him for over two years and hope to retire with him and his company. He models such great leadership skills by being sure to listen to what his employees have to say. He values work-life balance and makes sure that his employees are well taken care of in the workplace and outside of it as well. By having a boss that is so authentic, innovative, generous, and kind, I can say with confidence that I hope to continue working for him for the entirety of my career. Read more>>

Andrea Caprio

My mentor and teacher Cynthia Pasquella with whom I studied to become a Master certified transformational nutrition coach. I have learnt from her how important it is to address the root causes of my client’s health or weight issues, understand that we are all different and develop a personalized solution for my clients that take physical, emotional and spiritual health into consideration. Read more>>