Why You Should Look at Everyone From Your Barista to the CEO of Google as a Potential Mentor
If two heads are better than one, why wouldn't even more heads be even better?
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You wake up from three hours of tossing and turning to see big news from your prime competitor at the top of your Twitter feed. With neither the time nor the stomach for breakfast, you rush out the door with a rueful glance at the bike gathering dust in the corner. ClassPass? Oh, that's just a recurring bill on your credit card. A little back pain and weight gain is a small price to pay to achieve your dreams, right? At least that's what you keep telling yourself. (You'd tell your friends, but lately friendship is another thing you don't have time for.) Meanwhile, the life-and-death decisions keep coming -- one false move and you'll kill your company, let down your team, ruin your life. Just keep your game face on, never show doubt or fear, keep those personal needs in check. This is how it's supposed to work, isn't it?
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Look, life as an entrepreneur, especially in Silicon Valley, is hard enough without turning it into some kind of solo endurance test. Everybody needs someone they can turn to when the going gets tough for a reality check, a dose of strategic or personal perspective, even just a sympathetic ear. If you're going to last in this game, you need a mentor. If you don't have one yet, find one -- ASAP.
First, let's consider the wrong way to find a mentor. I'm an expert on this because it's the approach I used myself: Target the most important and illustrious person in your field, and keep on knocking in hopes that he or she will take you on. In my case, it was Sundar Pichai at Google, a few years before he rose to his current CEO position there. It wasn't a complete shot in the dark -- we had a few slight connections that gave me reason for hope -- but it was clearly a long shot. Sure enough, although he read my messages, we never got a chance to connect, and his fast-track career soon brought hundreds of other hopefuls competing for his attention. So, lesson one: Be realistic and pragmatic about identifying people who'll actually have the time to work with you.
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In aiming high, I had been trying to find the definitive mentor for my career -- a person who could coach, support and cheer me on for the rest of my natural business life. But, it just doesn't work that way. For one thing, our industry is far too dynamic to imagine that two people will remain in sync for the long term -- as both you and your mentor continue to grow and evolve, it's almost inevitable that one of you will outgrow the other, or you'll come into competition with each other, or you'll find diminishing returns from even the most promisingly launched relationship. Focus instead on the right mentor for right now -- the one who can help you reach the next level, and perhaps the level or two beyond that. At that point your needs may well have changed, but you'll also be in a position to gain the kind of mentor who would have previously been out of reach.
More fundamentally, it's also a mistake to think of your mentor in singular terms. If two heads are better than one, why wouldn't more heads be even better -- especially if each brings a different perspective to the table? The more angles you can consider on the opportunities and risks in your landscape, the fuller your understanding becomes, and the better your decisions can be.
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A framework for building your mentoring team
There's no point in assembling a group of mentors who all see things more or less the same way. Instead, consider people from all walks of life -- not just those ahead of you on the same ladder. I think of this in terms of a framework of five types of associates arranged in concentric rings.
1. First, there's the widest circle, the strangers -- the people you encounter casually over the course of the day, such as doormen, baristas and dog walkers. You're not necessarily going to sit down for a long lunch with them, but a passing comment or conversation here or there can be surprisingly effective for shining light in an overlooked corner or jarring loose a solution you'd been stuck on.
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2. Moving one ring toward the center, we find loose associates -- current and former coworkers, friends of friends, people you knew at school, the people you're seated near at a wedding or dinner party. Again, you're not going to go on a week-long retreat with these folks, but they can still add value in a group discussion.
3. The third ring consists of personal friends. They're not in your industry and can't necessarily provide domain expertise, but they care about your success and they're willing to think deeply over time about your business. They also understand your personal strengths, weaknesses and history -- a valuable asset.
4. The fourth ring includes industry peers -- the people you've risen through the ranks with, and who share a similar base of relevant knowledge, though often drawing different lessons from it.
5. Finally, at the innermost ring, there's your personal cabinet. These are the people most similar to the classic idea of a mentor: experienced, successful and as much of a stretch as you can manage. They won't have much time to give -- perhaps a round of specific questions or a meal once a quarter or so -- but when you do connect, their insights can be invaluable for helping you shape your thinking. At this level, quality is much more important than quantity; just one blue-chip adviser can make all the difference.
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Just as important, make sure you're talking to people of a variety of temperaments: optimistic, pessimistic, pragmatic, visionary. Balance your own intuition and tendencies with devil's advocates who'll prevent complacency and provide a healthy dose of frustration from time to time.
Of course, a mosaic of mentors from every part of your life will be somewhat more complex to manage and maintain than a single, all-knowing sage. But, this more diversified approach also avoids over-dependence on one individual's perspective, availability, and interest, and it allows you to bring new advisers into the fold and move on from others while maintaining continuity. Equally important, instead of merely digesting received wisdom, it'll be on you to synthesize these various viewpoints, accepting and rejecting aspects of each, to arrive at a complete and unified version of reality. That exercise in itself can be hugely valuable.
As I've practiced this approach in recent years, I've found it to have a transformative impact on the way I approach my business and my career. From my personal trainer at the gym to my colleagues at the top of the ad tech industry, I've found a world of diverse insights to help me see the field more clearly and make the right decisions more consistently. It's an approach that's within anyone's reach -- and one you'll never outgrow.
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