60 seconds with michael clegg: “when your future is compelling, your present is purposeful.”

Michael Clegg – also known as “Clegg” – has really been through it the last few years. And as a guy who plants the flag for the philosophy “Leaders Go First”, he knew that there’s power, freedom, and healing in sharing that process and journey out loud – for both himself and others. It’s showing up in an entirely different way.

In 2024, on the TEDx stage, he shared the details of experiencing a deeply traumatic and life-altering car accident. And, in doing so, I think Clegg reclaimed some of his personal and professional power, which is oftentimes what happens when we have the courage to reflect on our experiences, organize our thoughts, and then stand up to articulate out-loud how we go through the fire and come out the other side.

Clegg started as a see-you-once-a-month-networking-connection of mine through Vistage almost five years ago, and, today, I’m honored for toth shop to call him a client and a friend. 

– meg 

toth shop (ts): Your philosophy is "Leaders Go First." Now that your children are growing up and making their own life choices, what does "going first" look like as a dad? 

Michael Clegg (MC): At this point in my life, I'm trying to model ownership, gratitude, and generosity. I still have a fourteen-year-old daughter, so that keeps me young.

ts: In your 2024 TEDx Talk, you talk about a deeply traumatic, life-altering event – and how in the aftermath of that time you rediscovered your purpose and found your future self. For anyone reading who feels like a sudden crisis or setback has derailed their life, what is the first step to reclaiming their narrative?

MC: You have to have hope. And I don't use that term lightly. When your future is compelling, your present is purposeful. That drive to be your future self becomes the standard. All of those standards drive the actions required. The trauma from the accident was one thing. The financial ruin that followed felt much worse at times. 

ts: You’ve coached both C-suite executives and high school football players. What is the biggest common denominator you see between a CEO trying to win in business and a teenager trying to find his way on the field? 

MC: My answer would have been different a few years ago, but now I'm convinced it's learning how we show up to other people. I see so many executives who, because they've had some success and gotten to where they are, have stopped doing the things that got them there, like being present for their teams and lifting others up around them.  

When these high school kids get college offers, they tend to see that they have crossed the finish line instead of realizing that that is just where things begin. In both cases, they disregard all of the work and effort that got them there. They stop receiving feedback from their peers. And more importantly, they stop asking for it.

ts: You’ve spoken & written about the difference between being "nice" (avoiding discomfort) and being "kind" (having tough, transparent conversations). From a performance standpoint, why is choosing kindness over niceness so critical for unlocking a team's potential? 

MC: When I give my keynotes, and I ask, "How did I do?" and someone says, "I think you did great." They might genuinely think that I did well. For purposes of continuous improvement, it doesn't give me something concrete to work on or to improve. If I ask for advice and say, "Give me one or two things that I could do differently to make this better," providing I have a trusting relationship with this person, their response will be very different.

Most people prioritize their personal comfort over providing truthful data points for improvement.

ts: Every person we interview answers this same question last – Mile 18 is generally considered to be one of the hardest miles in a marathon. You’re hitting a wall; you’re forced to dig deep. What’s mile 18 in your line of work, or at a point in your career, and what do you tell yourself when you find yourself in the middle of a mile 18?  

MC: Since I've only run a half marathon, I can honestly say it was miles 10 and 11 where my legs started cramping. I would suggest that mile 10 or 11 is likely someone who is getting coaching but is unwilling to make the changes. And that usually means that they don't believe the feedback that they've received. I've had to let go of a few people for my own self-preservation, and I've explained exactly why I stopped working with them in both cases. 

Overall, regarding my work, I think it's beautiful. I can't imagine there being a mile 18 in this line of business. Recently, my dad made a comment to me where he said facetiously, "Are you still working a hundred hours a week?" I honestly was able to tell him, "Yes, I still work a lot, but I love what I do." When people become fully self-aware and can identify their triggers and understand how they land with other people, the sky's the limit for them.