3 Ways to Tell If You Have a Great Mentor

In the past I’ve written about how giving back is an important part of being an entrepreneur. It’s a small world and the more you give to genuinely help in the success of others, the more others are more likely to help you when you need it; paying it forward always pays off. But what makes a good mentor? How do you know when to act on advice or simply smile and nod? My chief mentor recently gave me some advice that fundamentally changed a course I was on (and likely accelerated my new venture by months if not all together might make our new company). Over the years I’ve listened to good advice and bad advice (and probably gave enough of each). So, here are the top three things that make for a great mentor. If you have a mentor that hits on these points then good for you. If not, get one, you’ll be happy you did.

1. Listening

A good mentor listens first. They ask you to share your story, your challenges, and ask you what’s important to you and your team. They take the time so that when they give advice it’s to your benefit not one size fits all. Building a company with the end goal of selling it fast and buying a house is very different than aiming for a billion dollar empire. Your strategy, planning, and how you approach issues change and so having a good understanding of the plan is important. Things to look for that mark a good listener:

a) They’re giving you their attention (not responding to text messages or glancing at their phone every 5 minutes).

b) They ask pointed questions based on what you are saying, challenging you to think deeper.

c) They can whittle down what you’re saying to a few core points and play them back to you so that together you can chart some focused next steps.

2. Context

I’ve written before about how important context is; the ability to speak from experience is huge. They’ve been there and done it or have been part of a team that has been through similar challenges you’re facing, whether as an entrepreneur, executive, investor, or board member but make sure:

a) They were in the weeds not simply an observer to the challenges and how they were solved. You don’t want someone who wasn’t in the guts of the issue.

b) They’re able to quickly understand the heart of the issue and come at a problem from various angles. You don’t want someone who shoves a solution down your throat because they’ve seen it solve a related problem.

c) They’ve seen similar problems a few times before and can tell you how they were solved in either the same or different ways.

3. Genuine

The best mentor is someone who you’d be happy to have over for dinner during the holidays. They’re helping because they actually care; they believe in having a Good Network. Here’s what to look for:

a) You are not paying them. Paid mentors are called advisors and generally earnbetween 0.25-1% over a few years in exchange for dedicated time. You might one day ask a great mentor to be an advisor, formalizing a relationship that was good to begin with (and giving back to them because they’re so great).

b) They know what they don’t know. They don’t have an answer for everything and are not shy about saying so. They’ll either point you to some resources or (if you’re lucky) hunt down an answer for you.

c) They don’t care about ‘owning’ the relationship. A good mentor is happy to connect you with someone who might help on a specific need where they can’t. The relationship isn’t transactional, they actually care that you do well.

I’ve had both good and bad mentors and I’ve learned to tell the difference. At this point I’m thankful to have a handful who are phenomenal but my go to guy, my Chief Mentor is a great guy we’ll call Howard (why? because that’s actually his name :)). I can write a few blog posts about how the advice Howard has given me has shaped the way I think about building a company and what it takes to win. I’ve counted myself lucky to have him on my side and now he’s doing something truly great. Howard is donating his time to growth/later stage companies he might be able to help and in exchange asking them to donate a small amount to the Upside Foundation, an incredible charity. Everyone wins, the companies gain insanely good advice, Upside can change the world, and Howard…well he’s just happy to help because that’s the kind of guy he is.