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.

Amy Giggey

The best boss I ever had, taught me how to think so I would know how to do. I would ask him for guidance and he would either give me the space to figure it out on my own, or ask me questions to lead me to an answer I may have already known. It can be so difficult as a boss to not point out the right answer or just do it because it would be faster. He took the time to show me and invested in my knowledge and confidence. I use the skills he taught me every day in my professional life and as a parent. The last gift he gave me was empowerment. Once, he told me I had a voice and he wanted to hear it. That was a moment for me where I felt seen and valued and it gave me the confidence to stand a little taller and speak a little more boldly. Read more>>

Grady Olson

I have two, both my current bosses, Erik Gonzalez my Creative Director at Media.Monks and Victor Gonzalez who founded Gross Magazine, not related at all but both first generation mexican-americans. They both found me when I was still unsure how to navigate with who I was and how to express myself. But they saw something in me that I didn’t know I had yet. Most importantly they saw who I was and could be. They allowed but also really pushed me to just be as open and myself as I can. Both helping shape me as a human being and working artist. They trust me with what I think and really challenge me to think bigger. I honestly don’t know where I’d be without them, probably back living and working on this avocado ranch I used to work on writing poems for myself, smoking cigs, and mad at the world. Read more>>

Jonathan Bird

When I started my career in financial services as a customer service representative, I worked for a manager named Evan Soso. One of the first questions he asked me was what my long-term goal was. I shared that I wanted to start my own investment advisory firm someday. After the initial shock, he shared exactly what the pathway looked like and what I needed to do. He supported me every step of the way and was a huge advocate for me which made all the difference in the world. Fast forward six years and I successfully launched my firm. Today Farnam manages over $100 million for clients around the country. I’ve told him before and I’ll tell him again, “Thank you, Evan!” Read more>>

STEVIE KLICK

My first boss ever was fantastic! She was a friend of the family, so I had known her most of my life. She owned two shops from a popular franchise located in malls. I started working for her just before I turned 15 and worked for her for about 7 or 8 years. This job got me through high school, University, and the subsequent traveling years of my life. She always welcomed me home and would squeeze me into the schedule when I needed the extra money. She had what seemed to me at the time, high expectations for staff, and customer service but she exemplified this herself, was great to work for/ with, and paid a good amount above average. She hired mainly women as ‘boys were too much trouble’ and the floor space was tight. She cultivated a fun and enthusiastic environment for us which was motivating. Most of us ended up becoming good friends, some, lifelong friends. In fact, my first employee was a longtime friend whom I worked alongside and under since I began. Read more>>

Kate Dodson

The greatest leader/ best boss / incredible mentor in my life is Lonnie Thomas, Director of Markets. She has been the manager of the Sunday Street Market in Detroit’s historic Eastern Market since it’s conception and over the years Lonnie has offered me countless opportunities to display & sell my work at events in the district. One of my early summers vending Lonnie offered me the opportunity to participate in a huge event, Eastern Market After Dark. I was unsure if it would be a success, but she always finds the perfect spot in the market for each vendor and I ended up meeting some serious art collectors that night that spent a generous amount of time and money with me. Read more>>

Dr. Jay Augustine

When you hire good people, there’s never a reason to micromanage. Trust your hire to do what you believed they could do, or would do, when you hired them! Years ago, much earlier in my career, I had two great bosses who most certainly fit this bill. Immediately after graduating from Tulane Law School and being admitted to the bar, I was as a judicial law clerk for the Honorable Bernette Joshua Johnson, the first African American to serve as chief justice of the Louisiana Supreme Court. Years later, after having successfully practiced law, while also holding publicly elected office and teaching law, I was appointed by Louisiana’s 55th governor to serve as deputy executive director at the Louisiana Workforce Commission (the former Department of Labor), where I had the honor of being second-in-command to Curt Eysink, the Workforce Commission’s executive director. Read more>>

Jalyn Webb

The best boss I have ever had i the one I have currently. He is kind, and firm. He has a passion for theatre and the arts, and most importantly for people. He cares about his team, and also the audience that we serve. I don’t know anyone that has the level of integrity that he has, and I am so grateful for his leadership. Read more>>

Sam Megraw

I have a history of bad bosses. I’ve been hit on by a sales coach, called names by a Chef, and had a boss that tried to pay me in IOU’s. I thought working in the yoga industry would be different but quickly learned these bad apples can be employed in any kind of business. So soon after I began teaching yoga, I found a woman who was everywhere, working hard, professional resume, sponsoring community events, doing things against the norm to better society. I still remember asking her to sit down with me and begging her to mentor me. She very casually said “I can probably find something for you to help with, let me get back to you.” And it started my favorite job of six blissful years as the studio manager of True Love Yoga. Read more>>

Lauren Wilcox

Candon Murphy – she’s the epitome of a good boss. Even as a lowly intern, she proudly dragged me around to corporate events, hyping me up to her long list of network connections that ultimately landed me my first job in lighting. To this day, she’s someone I reference regularly from a leadership standpoint! Read more>>

Blake Williams

Andrew Rurik. Go read his post. Andrew and I were working on a little short film called Open (which won awards, by the way!). We drove to some mountains nearby so that he could shoot some footage of me walking. Just walking in the brush. Imagine two people with backpacks full of gear, driving above Arcadia and walking out-of-breath on these hiking trails, while people who had trained their hiking muscles during the entire pandemic (there was nothing better to do!) sprinted right past us. But, although the goal was to portray me as a relatively outdoorsy person, this is not the story. Read more>>