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Shared experience can be the most rewarding part of business 

A few weekends ago, my son Connor had a group of entrepreneurial friends out to my lake cabin. We hung out on the dock, played games, enjoyed meals together and talked around the campfire. I admired the creativity and enthusiasm of the young men and women as we discussed a wide range of topic.

click to enlarge Tom Simpson
  • Tom Simpson

On the following Monday, Connor was reflecting upon the weekend and commented that one of his friends had said, "Tom will dad anyone." Initially I was unsure what he meant by this, with "dad" as a verb, nor was I confident it was a compliment. He clarified that the statement implied I took interest in other people, adding that I wasn't shy to offer unsolicited advice and guidance.

Viewing what Connor said through rose-colored glasses, I made a parallel between my interaction with his group of friends and mentorship. Mentorship is frequently discussed as an important component in the development of successful entrepreneurs, yet it's a subject that is vaguely understood and often misinterpreted.

As I look back upon my career, I benefited from four different mentors, each at key moments, undertaking new jobs or professions. Interestingly, however, I didn't know they were mentoring me, or realize the impact of their influence until many years later. Equally enlightening, I doubt each of my mentors consciously intended to become a mentor to me. Mentorship cannot be arranged or forced, it generally occurs naturally.

Mentorship begins as some form of relationship between an individual and someone in a position of influence over them (a boss, co-worker, colleague, investor, etc.) and develops as they gain mutual respect for one another. The mentor sees tremendous potential in the mentee, and the mentee values the experience and contributions of the mentor. They also enjoy each other's company and, often, a close friendship develops.

Although mentorship may be accidental and unintended at the start, a presumptive mentee needs to be open to accepting advice. They cannot have a naïve or brash sense that they know it all.

A mentor is not someone who always tells you what you want to hear. They support you in decisions they agree with, open doors for you, point out opportunities and challenges and constructively warn you of potential pitfalls.

On the other hand, mentors need to allow a mentee to make poor decisions and learn from those mistakes. One of my mentors frequently said, "What doesn't kill you makes you stronger." So true, but it is also important for a mentor to prevent a mentee from making fatal choices.

Effective mentors warn mentees of potentially poor outcomes and steer them away from destructive ones in various ways. Most obvious is simple, direct communication, as in "don't do that." I haven't found this to be an effective means of altering decisions otherwise made by bright and tenacious young adults. War stories from a mentor's experience, however, are more influential.

Leading by example is of equal impact. When I was a fresh investment banker, I shadowed my mentor as he solicited clients, prepared for meetings, led discussions, performed analysis, negotiated deals and celebrated the closing of a transaction. What I learned from observing and working alongside him continues to serve as my north star in business dealings.

One surprising subtlety in the mentor/mentee relationship is that the mentor is not always right. Since mentors typically have several more years of experience than mentees, and because business models, markets and technology are constantly evolving and being disrupted, mentees may have more innovative or efficient solutions. Additionally, a mentee likely has a different style, approach or risk tolerance than their mentor. It's important for mentors to understand these dynamics.

I feel I've been successful if someone I am mentoring accepts 60 percent of my input. In those cases where my guidance has not been followed, the constructive dialogue has often resulted in better results. I aspire to learn as much from those I have mentored as they have learned from me.

The motivation to mentor is altruistic. It's purely out of selfless interest in the success of the mentee based on recognition of their talents and the opportunities before them. Having said that, mentorship is among the most fulfilling of life experiences.

A close friend of a person I was mentoring once interrogated me as to why I was being so helpful and what was in it for me. It wasn't clear to her at the time, but it is now.

As time goes on, life happens, people move and mentors and mentees may lose contact with one another. Yet the nature of the relationship continues. My last mentor, community leader Dave Clack, continues to influence me today — in all walks of life.

I was recently skiing in Sun Valley and ran into Dave, who is very gifted on the slopes. After a few runs together, he asked if I was open to some pointers. Two hours later, although I fell a couple of times, I was skiing better than ever. Dave and I each had a great day on the mountain. And for me, that pretty much summarizes mentorship. ♦

The original print version of this article was headlined "Mentor It Forward"

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