Master Mentorship (Mentoring the Mentors)

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Master Mentorship (Mentoring the Mentors)

This is the mentor’s craft: how do you actually mentor well? Throughout the session I was essentially coaching the two mentors in the room, Tom and Matt, on the symmetry of this, because so much of what makes a great mentee also makes a great mentor.

A Great Mentor Has Impact: Getting to the Aha Moment

What makes a great mentor is somebody who has an impact. Mentorship is a gift, and the gift that really makes an impact is one that feels good. If you give somebody a gift and nothing happens, that doesn’t feel good, and it happens on either side too often. When you have real impact, somebody says “wow” at the bottom line, or “aha” at the top, that personal moment of realization. That’s the most rewarding thing a mentor can see in a mentee.

How do you get to the aha moment? As a mentor, keep asking: what have I done to move this process forward? Chess is a great analogy, because there’s no simple right or wrong; the greatest supercomputers took years to beat the masters, because it’s not that logical, there are so many pieces. In mentoring relationships there are usually so many different aspects to somebody’s question that to get them to the aha moment, you have to bring out approaches that get them thinking about the bigger picture. You’ve not just given somebody a chess move; you’ve given them a whole basis on which to play chess, and gotten them to think about how they’ll develop their own strategies.

Answer Questions With Questions (Guided by Frameworks)

If a mentee asks “should I price it A or B?” and you say “A,” you’re not helping them. Instead, get them to think about the whole approach to pricing. As a mentor, painful as it is, answer a question with a question: “What is the core value of what you’re selling, and how might you deliver that?” People hate it when you first answer their question with a question, but out of it comes a more focused thought about the core value of the product, how the customer is using it, what value they see, and therefore a pricing strategy that reflects that value, which is much deeper than just a number or a model. As the mentor, I know in my head that the framework for why people pay for things is usually based around value, so I throw it back: “Where’s your value? How might your customers consume that value? What’s the basis on which they’d find it most easily packaged?” I could think of a thousand questions around pricing; that’s my job.

So mentors should answer questions with questions, painful as people find it, but do so in a way that’s guiding, with things like frameworks. And mentees should ask their mentor for questions: “You give me a lot of great ideas, but I’d like you to ask me more questions.” If you’re not getting the light bulb to go on, if you’re not having your own aha moments, it’s probably not the deepest, most significant relationship it could be.

What You’re Trying to Develop: Curiosity and the Confidence to Try

Following the symmetry, what are you trying to develop in your mentee? Curiosity, the joy of learning, and a very important thing: the confidence to try. If you did nothing else as a mentor other than give your mentee the confidence to try stuff, you’re a good mentor. As one mentee put it: even if you never gave me the CTO or taught me how to hire, if you gave me all the confidence in the world to go figure out how to find the greatest CTO, “it’s like lighting a fire that’s going to keep me warm until the next time I need it; it’s like kindling a fire that you need.”

Startup Secret (my number one thing I tell entrepreneurs as a mentor): there is no such thing as failure; there is only learning. I want to give you the confidence to try even if you fail, because I have learned more from all my failures than from any of my successes. So look for a mentor who gives you the confidence to act and the comfort that it’s okay to learn.

Relating this to sports, as Tom did (his wife is a professional coach): think of the athlete–coach relationship. The confidence part is what really resonates, because the level of productivity of an entrepreneur, the delta on it, is so much higher when they’re confident, willing to try, explore, experiment, and learn from mistakes. The mentor I look for encourages you beyond anything else, so it feels like there’s nothing you can’t do. There’s a wonderful quote you’ll never guess who said: “There’s no such thing as impossible; in fact, the word itself spells I’m possible.” Audrey Hepburn.

Record and Review, and Keeping It Mutual

A good mentor helps you see that things are never as bad, or as good, as they seem, and helps you reframe when you’re down or temper your enthusiasm when you’re carried away. And a good mentor keeps checking whether the relationship is working, and asks the mentee how to help more. The mentor’s job is also to get to know how the mentee thinks, and, when they keep getting stuck, to do a debrief and understand whether it’s a pattern. Do all of this and you get that aha moment, the most rewarding thing a mentor can experience, a huge win-win flywheel of positive reinforcement.