Mentoring todo list written in a notebook
Influential Leaders
by Don MacPherson

eddy was a gangster. There is no other way to put it. And he was proud of it. When I showed up for my first day as a volunteer at the county juvenile detention center, I knew I was outside my comfort zone. I had no idea that Teddy was going to extend that comfort zone throughout the better part of a decade and take me hundreds of miles away from home.

Finding Myself as a Leader
I have a long list of mentors who have helped me develop personally and professionally. However, it is being a mentor that has influenced me most as a leader and as a human being.

When I met Teddy, my job wasn’t fulfilling. It paid for my student loans and other bills, but I was searching for an outlet that could truly make a difference. That’s why I started volunteering with young people. I love teaching and coaching.

When I heard about tutoring opportunities offered through my employer, I jumped at the chance. It turns out that I was the only employee who chose to volunteer. Everyone else at the company missed out on a chance to change a life and have their own life changed at the same time.

Teddy and I would meet for a couple hours each week. He would choose a topic of interest, I would research it, and we would discuss it the next time we met. He loved it. I loved it. I got the sense that all his male role models prior to meeting me had a criminal background. To him, I was exotic. In truth, I had never met someone like Teddy either.

At the time I had no idea how much this experience was going to mean to my development as a leader. My success in the detention center required me to build trust, project confidence, assess risks, communicate with people who were different from me, and, maybe most importantly, listen without judgment. Leadership development opportunities can come in some of the most unusual settings.

Leaders Bond
Despite our vast differences—race, economics, education, criminal history, etc.—Teddy and I formed a bond. I can look back now and call it love. Teddy might describe it as brotherhood. Regardless, the bond was there. I know this because Teddy showed me.

One night before our tutoring session started, I joined Teddy’s unit for dinner. After fixing my plate, I sat down at a table with a couple of Teddy’s peers. Teddy was in the buffet line talking to one of the guards. A young man named Wallace started aggressively asking what I was doing at his table. Wallace easily outweighed the next largest person in the unit by 50 pounds. His taunts incited others at the table to join him in making me uncomfortable.

Fights were a common occurrence, but harming a civilian like me would have had harsh consequences. I didn’t know if they were going to escalate beyond letting me know I didn’t belong with them, but it didn’t matter.

As if he had a sixth sense, Teddy, who was 30 feet away with his back to us, knew the energy in the room had changed. He left the food line, shot over to our table, and put his nose six inches from Wallace’s face. Teddy let him know that I was his tutor; if Wallace had a problem with me, he had a problem with Teddy. Wallace, his eyes wide with panic, simply deflated. Wallace never talked to me again that night or any other night. Teddy put himself in between me and a potential threat. Love, loyalty, brotherhood—however you want to define it, the bond between Teddy and I was present.

Connections Matter
When Teddy was assigned to an adult prison, we vowed to stay in touch. We wrote to each other. His mom and I even wrote to each other. A letter from Teddy was a prized possession. I would let it sit on my counter for a day or two before opening it just to enjoy the anticipation. After several years of his incarceration, Teddy included a document with one of his letters. Unbeknownst to me, Teddy had been studying while in prison. The document he sent me was the original copy of his GED.

After five years in prison, Teddy was released and invited me to visit him in Kansas City. I drove the 400 miles to see him. When Teddy opened the door, I couldn’t believe my eyes. Not only had he earned a degree, he had transformed himself into a chiseled hulk. He pulled me into the apartment and hugged me like his life depended on it. Physical contact in the detention facility had been prohibited. This was our first hug.

More than coaching or training, mentoring has a power to develop careers and character like nothing else.
Teddy took me to lunch, we went to the mall, and we saw a movie together. Teddy wanted to show me where he grew up. He wanted to bring to life the stories he had told me years earlier. I even got to meet his mom. She thanked me for supporting her son throughout the years.

It’s been nearly 30 years since Teddy and I first met. I haven’t seen him or talked with him since spending that day together in Kansas City. He reoffended and spent the next 20 years in prison. He was a gangster. He knew no other way.

Discovering My Life’s Purpose
If you ask any successful person about their mentors, they are likely to rattle off a list of people who have formally or informally influenced their careers. More than coaching or training, mentoring has a power to develop careers and character like nothing else. That’s why I have mentors and that’s why I mentor. I want to make a difference. I benefit by learning from the people I mentor—what they value, what their challenges are, what fills them with joy, and even what the next trends might be.

I often wondered who Teddy could have become if we had met earlier in his life. I suspect he might have turned out differently. Maybe he would have taken his education more seriously or developed into an athlete. Being in a gang gave him purpose and a brotherhood. Maybe he could have met those needs in a more positive place.

Playing this “what if” game is part of the reason I have defined my life’s purpose as helping people realize their full human potential. Throughout the decades since meeting Teddy, I have put this purpose into action by advising entrepreneurs, mentoring young professionals, being a Big Brother, helping young people elevate their education, creating sports teams for disadvantaged kids, and developing leadership opportunities for high-potential young people who often get overlooked.

Leaders Are Always Learning
Effective leadership requires a broad range of capabilities. We are expected to build trust, motivate, give feedback, and manage change while being empathetic with diverse groups of people in dynamic situations. Mentoring has prepared me for all of these challenges.

I had never met anyone like Teddy. By listening to the stories that were important to him, by letting him teach me, and by accepting him despite his transgressions, I was able to earn his trust. We didn’t get hung up on our many differences. We found interests that connected us.

Years later when I became a Big Brother, I started to learn about motivating employees. I learned that recognition, a sense of meaning, and growth and development were powerful tools of motivation. At the time, I didn’t have a team of my own, so I tested my skills on my Little Brother. I practiced recognizing him, filling him with meaning, and focusing on his development. When I got my own team, my motivational skills were sharp.

Leadership Is a Circular Endeavor
One of the most important lessons I learned from the young people I mentored was to listen and learn. My mentees wanted to teach me as much as I was trying to teach them. Teddy told me the most effective way to break into a car. Another mentee explained how to keep getting phone service even if I was late on my payments. These weren’t necessarily the lessons I hoped to apply in my life, but what this did was develop my non-judgmental listening skills. The other gift it gave me is incredible empathy for the challenges some people face in their everyday lives. My gratitude was fortified and my empathy blossomed.

Throughout the course of my career, the workplace has become more and more diverse. Creating a sense of belonging with every person on their team is one of the most important things a leader can do. Leaders are required to connect with people from a wide range of demographics and backgrounds. Building trust and creating connections are critical in this process. Being a mentor gave me opportunities to hone these skills with young people of different races and economically challenged backgrounds, and even with their families, who often pre-judged me because of how I looked and talked.

When I tell these mentoring stories, people are often envious. When I ask why they don’t mentor, many say that they don’t have enough time, expertise, or experience, that mentoring someone from a different background is intimidating, that they aren’t very good with kids. A few say they will help others once they get more firmly established. Here are my responses to these excuses:

1. If it’s important to you, you’ll make time. My two young children often accompany me when I meet with mentees. Everyone benefits.

2. Mentoring someone with a different background is a great way to leave your comfort zone. Getting outside your comfort zone is the entry point to your growth.

3. Kids aren’t the only people in need of mentors. All of us can benefit from having mentors. I’m in my 50s, and I still have several mentors.

4. Being a mentor and reaping the learning and growth opportunities it provides is one of the best ways to establish yourself and your career.

I promise you, there is someone in your organization, someone in your neighborhood, or someone in your network who can benefit from your mentorship. By being a mentor, you are positively changing a life. Sometimes that life is your own.

Today, Teddy, after serving another 20 years in prison, is a free man. I have tried to get in contact with him but to date have been unsuccessful. I would simply like him to understand what he meant to me and how he helped me become the leader I am.

Don MacPherson Headshot
Don MacPherson travels the world interviewing geniuses about trends shaping the way we live and work for the podcast 12 Geniuses. MacPherson also helps organizations create incredible experiences for their employees. A five-time entrepreneur, MacPherson has spent 25 years studying the employee experience, the attributes of great leadership, and how healthy organizational cultures are created and sustained.

An avid traveler and volunteer, MacPherson has visited 74 countries and been a Big Brother mentor for more than 20 years. He has helped create The Inner City Ducks, Future Leaders Academy, and Leadership Garden—all organizations focused on helping young people reach their full potential.