Demystifying mentors


By Ray DePaul

I recently had an opportunity to attend a day and a half mentoring workshop with some incredible people that put my relatively minor achievements in perspective. At the opening dinner, we had to introduce ourselves and tell a story of how a mentor had made a positive impact on our lives. My mind starting racing. It hit me that I don’t think I ever had a true mentor. As the others told moving stories about the people who changed their lives, I reached deep into my history to tell a downer of a story.

My first brush with mentorship came in my first job at a software startup. At the time, I had two young kids and a promising career in the technology industry. The president of the company took a liking to me and was very generous with his time. I remember vividly one day as my newly minted mentor said to me, “Ray, if you don’t let that family crap get in your way, you’re going to go places.” That was the moment I realized that he was my boss, not my mentor. We had completely different value systems and goals. I was disillusioned. Instead of seeking out a more suitable mentor, I stopped looking and settled for a series of highly intelligent bosses. 

It wasn’t until I started working with young entrepreneurs that I realized what I had missed out on. While still in Waterloo, Ontario, I had the pleasure of spending every other Friday with Eric Migicovsky, the founder of Pebble. Eric is a remarkable young man who went on to literally create the smartwatch industry. Although I was supposed to play the wise, experienced role in the relationship, I can honestly say that I got as much out of these discussions as Eric. Was this what a mentor relationship was about? The word mentor was never used. We started with having coffees and then meeting in his office, which was simply a converted garage. I asked questions, provided some input, and made some introductions. He challenged me, introduced me to a new industry, and opened my eyes to the amazing capabilities of young 20-somethings. I’m proud to say that I now have a similar relationship with dozens of young entrepreneurs and students.

I encourage you to do as I say, not as I did. Build relationships with people you admire and respect. People you can learn from. People that you can help in return. You don’t need to “pop the question” and ask them to be a mentor on the first date. Just humbly offer to buy them a coffee to learn more about their career. Anyone worth talking to will find a way to say yes to that request. Then ask an open-ended question about them, shutup and listen. If you want to impress them, impress them with your listening skills and the thoughtful way you humbly add to the conversation. Then have another coffee… and another.

There’s nothing magical about a mentor. They are simply people that can coach, advise, and champion you. Unfortunately you will experience the odd mis-match just as I did many years ago. That’s fine. Recognize them for what they are (a boss, a business advisor, an idiot) and continue searching for true mentors. If you surround yourself with a few well-meaning mentors, you will be miles ahead of those, like me, who try to do it all on their own.