Jennifer Sawyer, writing in the Dailyworth Work column, has an excellent list of traits to look for in a mentor. While like many other articles about mentorship this article is focused on career mentoring, not founder mentoring, these traits apply equally well to the mentors of entrepreneurs.
Here is her list with my comments appended:
They’re Different (Enough) From You
Typically mentors of founders tend to be former entrepreneurs or business people who have had success and want to pay back. And typically founders are far younger, with less gray hair! So the superficial characteristic of age is an easy difference to chalk up. But be careful of other traits, especially if you are in an academic mentoring program. If you majored in computer science you may well want a mentor who majored in architecture and design instead of CS. Chances are you already know your former professors and peers in C.S., but don’t know anyone in the design field. Given the importance of design in today’s product development process you’ll benefit from that difference. And the converse is equally true. If you majored in graphic arts you may want a mentor with a C.S. education given the importance of data analytics and software in business. So look for a different, but complementary academic background.
They Have Wide-Ranging Interests
Studies have shown the value of curiosity in founders. But how do you measure or even detect curiosity? One way is by how widely a person’s interests range. So no matter how accomplished a prospective mentor may be, if he or she is very narrowly focused, say purely on how to build successful ecommerce companies, even if your interests align, you will benefit from diversity of thought, experience, expertise and contacts. Is your prospective mentor a lifelong learner? Do they participate in non-profit activities as well as business activities? One thing you are looking for in your mentor is perspective, a point of view different from yours. Otherwise you risk creating an echo chamber effect where your mentor may think so much like you that neither of you will spot a serious flaw in your business plan.
They Push You Out of Your Comfort Zone
Mentors give feedback, offer advice, and provide guidance. But if you really want to grow as a founder you need a mentor who will push you in the direction you need to go, but might be uncomfortable going. A great example is doing customer interviews. Many people are very uncomfortable approaching strangers, or even if they are introduced, talking with them. But the post-docs in the National Science Foundation’s I-Corps program for entrepreneurs are required to talk to as many as 100 prospective customers – not including friends, family or acquaintances. Often CEOs may want to delegate talking to customers to their sales director. This is a huge mistake! As a CEO you need first hand, not second hand, knowledge of your customers’ problems and what they think of your solution. So for technical people, going on a sales call may be outside their comfort zone. For a sales person participating in a competitive review of the company’s product may be equally uncomfortable. Your mentor should learn enough about you and your business to give you a gentle, but firm push in the direction you need to go when deemed necessary.
They Won’t Just Tell You What You Want to Hear
A key role of mentors is to provide feedback, for example on investor pitch decks. We have seen hundreds or even thousands of them. And more importantly, we know what works and what doesn’t. So very often we find we have to tell founders that either the format, content or both of their pitch deck simply won’t cut it. Even to the extent of telling the founder to start all over again. The saying amongst athletes is No pain, no gain. If a mentor is simply praising you to the skies that isn’t helpful. I’ve yet to find anyone who improved their skills or performance by hearing nothing but praise. What you need is constructive criticism; criticism aimed not at you as a founder, but at your pitch deck, proposed sales commission plan, or any other aspect of your business. While it might sting a bit to hear it, your mentor may well prevent you from getting really hurtful rejection down the line.
A mentor who has had success is necessary, but not sufficient. You want your mentor to be able to reflect back on their experience: what worked? what didn’t? Why? How did they recover from failures? What did they learn? If a life unexamined isn’t worth living, surely a successful entrepreneurial career unexamined is not worthwhile either. But while I often share my (many mistakes) with my mentees I ask them to be creative and make their own mistakes – don’t make the same ones as I did.
They Value People More Than the Bottom Line
I see my role as a mentor as very straightforward: to help my mentees succeed. However, sometimes it is not 100% clear what success actually means to a founder. Is it making a lot of money? Peer recognition? The joy in helping others? The reward of solving a tough problem no one else has cracked? Your mentor should help you clarify what you value, because only then can he or she really help you. As the saying goes, If you don’t know where you are going, all roads will take you there.
Take the time to get to know your prospective mentor, just like you would want to get to know a prospective hire, investor, or partner. Only by investing time – preferably face to face – will you be able to ascertain if your mentor has these important traits. And keep in mind, no one bats a thousand. Use these traits as guide posts, not filters. At the end of the day you need chemistry with your mentor, as mentoring is a reciprocal relationship – it has to work equally well for your mentor as for you.