When it comes to mentoring entrepreneurs rather than career mentoring, I’ve yet to find any formal training programs. The closest I’ve come is that the MIT Venture Mentoring Service runs an orientation program for all new mentors and presents best practices in mentoring at the monthly mentors’ meeting.
They list what they consider five compelling traits of exceptional mentors. I’ll list each and annotate them with insights from my own experience as a founder and as a mentor.
I’ve always had a reputation for being blunt. It probably ties in with the fact that I’m an impatient person. I hate beating around the bush. I want to get to the point. I just find candor is far more efficient, both for the mentee and the mentor. Occasionally being candid can raise the hackles of founders, such as when you list that it takes to be investor-ready and they see that their venture just isn’t. MIT VMS and now MIT Sandbox use team mentoring. So being candid is not only efficient for the founder and for me, it helps the other mentors as well. Sessions are as short as an hour, so there is no time to waste. But just because you are candid does not mean you aren’t diplomatic. The best way to do both is to ask questions rather than make bald statements. For example, for the company that wasn’t investor ready I listed the five elements needed to be investor ready and asked the entrepreneur how many his venture had. When he saw his venture fell short on three out of five of them he realized he wasn’t ready to raise money – I didn’t have to tell him.
2. Big-picture commitment
My mentoring focus is on the entrepreneur, not on the venture. Why did they start this venture? What goals do they have both for the business and for themselves? The more I understand their intentions – why they started the venture and what they are trying to accomplish, the more helpful I can be. Mentoring sessions can often veer off into the weeds if you are not careful. It’s up to the mentor to keep the discussion on track. Mentoring is for solving big picture problems like should the venture be a non-profit or a for profit company, not for discussing the design of their web site. Founders can help by bringing agendas that focus on major issues where they need guidance and by resisting the temptation to go down implementation rabbit holes.
What rewards me as a mentor is seeing the accomplishments and growth of a founder and their venture. Yesterday we had a session where the founder had some great accomplishments to share with us, adding two new experienced team members, closing an important sale, and finalizing a partnership he’d been working on for some time. It’s fun to encourage the founder at times like these. But it’s more important to encourage a founder when times get tough – when a major deal falls through, his co-founder quits, the term sheet fails to turn into an investment. Building a company is a grind and can be lonely. There are typically more losses then wins, especially in the early days. So I make it a point to encourage founders the most when they are down. As the football coaches say “You are never as good as you think you are when you win and you’re never as bad you think you may be when you lose.”
I believe in giving founders “homework” – that is to mutually agree on a specific milestone they will plan to reach by our next meeting. Mentoring tends to be focused on the short term – what does the venture need to be investor ready? to ship their first product? to recruit a sales director? Setting short term milestones keeps mentoring on track and keeps the founder accountable to the mentors. But we make it clear that it’s not our job to check in on the founder’s progress – we expect the founders to stay on track unless we hear something different from them.
Despite all the courses, books, lectures and blogs like this one, a mentor’s experience in starting, developing, and exiting a venture gets conveyed on a just-in-time basis. While we occasionally see founders who have built a company before, most are first timers and the stories we can tell to help them through issues they are facing are almost always well received. Frankly, if you haven’t ever started, built, and exited a company I don’t think you can be a successful mentor for startups. You may well have domain expertise in a particular industry like retail, or functional expertise, like sales, but these can’t substitute for the many zero stage issues founders face. In fact when a venture transitions from needed founding expertise to domain experience we know they are on their way to growing their venture. And because every mentor has different experience, team mentoring is more than doubly effective, as we bring different perspectives as well as different lessons learned from our experience to team mentoring sessions.
Check out the video at the end of the Inc. article 5 Compelling Traits of Exceptional Mentors Starting your own business is challenging. Accessing entrepreneurial experience can be the key to success.