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.

Ignacio

Well, my wife, Ximena, was the best boss I’ve ever had.

We met when we were young and have been together since college. After we got married, she became my boss. We worked together on most of our projects, including our personal stuff.

She was a trailblazing, small person with crazy and out-there ideas. But she taught me how to work towards our goals, and in the end, everything she touched became reality. Read more>>

Taylor White

As a professional, I am honored to say that I have been fortunate enough to have a few supervisors who were great leaders and mentors. It is hard to just choose one because if it wasn’t for these amazing people collectively, I would not be where I am today. Instead of making the choice of one, I will take you on a journey of those supervisors who helped me shape my path and navigate its challenges. Read more>>

Emily Quereux

Yes, I had a wonderful boss who eventually became more of a mentor figure in my life today. Her name is Lori Carman and she is the owner of Dream Dogs Bermuda Dunes. After I graduated college and moved across the country from Massachusetts to California, I felt really lost. I had no idea what I wanted to do for my career and where I could even see my future going. After doing some research in October of 2022, I reached out to Dream Dogs looking for an internship / volunteer work at the training facility. I had worked with service dogs in college, but knew that I needed more experience working with animals and instructing people. Read more>>

Annie Gunning

The first boss was, and still is, the best I’ve ever had. She was not only supportive, encouraging, creative, and enthusiastic, but also a true mentor who made work fun and meaningful. Because she had a background similar to mine, she truly understood the importance of my role and our department’s mission — something I’ve realized is rare over the past 20+ years. That shared understanding made a huge difference in advancing our goals in the field. Beyond being a strong leader, she genuinely cared about each of us, taking the time to listen to my ideas, encourage my growth, and offer feedback that helped me become better in my career. Read more>>

Calvin King

Throughout my life, I’ve been blessed with some incredible leaders—my parents, my older brother, teachers, coaches, mentors, and former bosses—all of whom played a vital role in shaping who I am. But if I’m being honest, the best boss I’ve ever had is… me. Read more>>

Katie Greenwood

The best boss I’ve ever had led with empathy, trust, and clear communication. They empowered our team, listened actively, and fostered a positive, inclusive environment. By recognizing achievements and encouraging growth, they inspired loyalty and drove our collective success. Their genuine care for both people and performance made them a leader worth following. Read more>>

Bethany Kroesing

Without a doubt, the best boss and mentor I’ve had as a therapist was a former supervisor named Ann. I knew I would like her the moment I had my interview when she asked me, “If we were to have an employee potluck, what would you bring?” I laughed and told her I’d probably bring the napkins and silverware —because I wasn’t sure anyone would want to risk trying my cooking. Without missing a beat, she said, “You’ll have to pick something else—I already called dibs on that.” Read more>>

Tracy Huff

The best boss I ever had was one of my first. At the time, I was an E-4 Specialist in the U.S. Army, working in the S-3 section, which managed all the training for our battalion. Our office consisted of sergeants, officers, and two specialists—myself and another soldier, Julie. Part of our job required us to interact with company commanders and first sergeants, many of whom would try to use their rank to pressure us into prioritizing their requests. Read more>>

Michael Monroe

I met my manager/boss on one of my first gigs. It was a smorgasbord restaurant during the day and an ‘all ages’ club at night featuring local musicians, improv troops, and foosball. I was 19 and she was 17 and she fell in love with me and my music. Love at first sight for both of us. She knew she should be my manager right away. Then 18 years of “ships passing in the night” and gigs she would attend with this underlying romantic scenario finally brought us together with this crazy notion that we could make a career for both of us. She left her executive corporate position in Florida to move in with me, a Minnesota musician. Read more>>

Adam Pener

I began my career as a researcher and analyst for national security legend, Hon. Roger W. Robinson, Jr., who architected the financial takedown of the Soviet Union for President Reagan. Roger was a friend, a mentor, an advisor, and — eventually — my business partner at CSAG. Together, Roger and I built the world’s only database of public companies that do business with governments that sponsor terrorism, triggering a national campaign called Terror-Free Investing. The company was a great success and it took me to meetings that were far above my paygrade at the time. All of which were valuable in my education and quite memorable, not always in a positive light. Who knew that there could be sides when it comes to defunding the bad guys? Read more>>