Mentoring the mentors: Advice and inspiration for startup mentors

Last year around the time PIE was starting, David Cohen, cofounder of TechStars, shared the TechStars Mentor Manifesto. And it served as an inspiration for me. A post by Micah Baldwin, a TechStars mentor who now heads up Graphicly, provided a similar nudge for me.

I saw David at the recent Microsoft Accelerator Demo Day and was reminded to go back and reread both of these posts. Inspired again, I thought I’d augment their mentor guidance a bit with some things that I’ve learned from observing PIE startups and mentors over the past year.

I shared these tips with the PIE mentors and a few of them suggested I turn it into a blog post. So I took that mentoring to heart.

If you’re thinking about becoming a mentor for startups—either in a formal accelerator program or independently—here are some tips for thinking about how to work with entrepreneurs.

10 tips for mentoring startups

1) Common sense is not common. Mentors often worry that they need to come up with some earth-shattering insights to be of value. This couldn’t be further from the truth. Fact of the matter is that you spend day-in, day-out working in your area of expertise. You make intuitive leaps that are all but impossible without having had the experiences you’ve had.

All of that—all of that built up knowledge—is of incredible value to an entrepreneur who is in the middle of a maelstrom of activity. Or who hasn’t yet gained the experience. So think of the simple things. Think of the obvious. And share those insights. Because your common sense is not common.

2) Your mistakes are often more valuable than your successes. While sharing your victories can be motivating for startups and entrepreneurs, being open about your failures and mistakes can often be more helpful. Mistakes are why you changed what you were doing. Failures are the things that taught you how to do your job. The stumbles and downfalls are the things that caused you to lose sleep, to stress, and to doubt. Share those. So that everyone can learn from them.

I always say that PIE is about “making new mistakes.” There are two reasons: 1) If startups are repeating mistakes our mentors have already made, we’re failing them and 2) If the startups go out and make new mistakes, then they can come back as mentors to prevent others from making those mistakes.

3) You don’t have to know everything. You were asked to mentor because of your experience. And because you’re awesome. But that doesn’t mean you need to know everything. Nor does it mean the onus is on you to know everything. You know what you know. Share that. You’ll be surprised at how seemingly simple things can drastically improve a startup’s potential and perspective.

4) You are more than your role or profession. This one became especially clear with our corporate mentors. Sometimes, you have to take off your “brand hat” and put down your business card. Sometimes, your most valuable feedback comes not from what your company would say but from what you would say. You are an incredibly talented individual who has made it to the position you’re in because of the decisions you’ve made. Sometimes, just being you and providing personal advice can be incredibly beneficial.

5) Know your limitations. Don’t over promise. Don’t under deliver. And don’t get yourself into a mentoring situation that has you feeling stressed. An hour of your time is valuable. If that’s all you have to give, that’s all we’re asking you to give. Don’t make this a chore. Mentoring is a reward. It’s the opportunity to share what you’ve learned. And to prevent others from making the mistakes you’ve made. It should be seen as such.

6) Advise as if you were an employee. Mentors are often driven individuals who have attained their position through sheer determination and hard work. They’re often people who take the wheel and try to steer others in the right direction. And they’re used to leading. But your role here is not to lead. Your role is to advise. And fact of the matter is, no matter how vehemently you support or oppose an entrepreneur’s decision, it’s their decision to make. And they have to be the one to make it.

Personally, I take this from the vantage of an employee or consultant advising his or her superiors. “This is my opinion on what should be done, but you’re the boss.” Mostly because I’m fairly sure I’ll be working for one these entrepreneurs one day.

7) Be honest. While mentoring can be a lot about bolstering the outlook for new entrepreneurs and motivating them to change the world, the most valuable mentoring comes from being honest. Not nice. But honest. Sometimes, your feedback will be negative. Sometimes, your feedback will be difficult. But it should always be honest and critical—in both the positive and negative sense of the word.

8) You can’t fix everything. Nor should you. You’re not here to rescue anyone. You’re here to provide startups with feedback on where they’re going. That’s all we ask. If you want to take an entrepreneur under your wing, please feel free. But don’t feel obligated to solve their problems. Your job is to push them to solve problems themselves. More often than not, the problems you see haven’t even dawned on them yet. So tell them. But don’t fix them for them.

9) Take it personally. We want you to be invested. We want you to be happy and frustrated and proud and confounded. We want you along for the roller coaster ride. We need you to take this personally. At times, it will be completely aggravating. (Trust me on that one.) But that means you’re taking it personally. And that’s what these entrepreneurs need.

10) Mentor one another. You’re not just here to give. You’re here to get. It’s a two-way street. So talk to other mentors. Get advice from the PIE startups. Get advice from Wieden+Kennedy. If you see another mentor in need of guidance—in need of your common sense—then pull them aside and share it. And be equally willing to listen when another mentor wants to impart their knowledge to you.

Good luck. And thank you for giving back.

If you’ve got some tips on mentoring, I’d encourage you to share them. It helps everyone.