What makes a good mentor?

Over the past six years of mentoring at MIT and elsewhere I’ve seen many, many mentors – MIT employs a team mentoring system whereby two or more mentors are assigned to an entrepreneur(s).

Here’s what I’ve seen from the best mentors:

  1. Great listeners. As the saying goes, “you don’t learn anything by talking.” Some of the very best mentors say the least.
  2. Great questioners. Mentors are good at asking not just asking good questions, but at the right time. You don’t want to interrupt an entrepreneur while in midst of a presentation or demo unless it’s really necessary. Good mentors are careful to ask one question at a time, then ask follow up questions. You don’t want an entrepreneur overwhelmed by a barrage of questions.
  3. Good mentors should have had some startup successes. If they haven’t sold a company, taken a company public, or done a successful merger they don’t have firsthand experience of what success looks like and how to help you to succeed.
  4. Good mentors should have failed at least once. As the saying goes, “If you aren’t failing, you aren’t trying hard enough.” But I tell my mentees, “Be creative, make your own mistakes, don’t replicate mine.”
  5. Raising money is important to virtually all entrepreneurs. So mentors who have raised money from angels, angel groups, VCs and corporate venture arms can help you with this very time consuming and difficult process. The more recent the experience the better, though some have said the VC industry hasn’t changed that much in 40 years. Many more changes have taken place in angel investing.
  6. I tell my mentees that their biggest enemies are not their critics, but “backpatters.” While it’s good to praise mentees when they are “doing the right thing,” what they need most is constructive criticism and feedback, delivered respectfully. Some mentors will take the “devil’s advocate” role, which can be helpful in getting the entrepreneur to “think different.”
  7. Since recruiting talent, team building, and corporate culture are so critical to a startups’ success your mentor should have significant experience in these areas.
  8. Good mentors are not academic lecturers: they ask, questions, tell stories, use analogies, cite data, challenge assumptions, and give examples. And they do so briefly and succinctly.
  9. Every entrepreneur needs connections, so if your mentor has a great network and can make useful introductions, that a big plus, but not a requirement.
  10. What not to expect: domain expertise. If you need someone to review your code or craft your social media marketing plan, you need an technical advisor or a consultant. If you don’t know the difference between a mentor, advisor, and consultant see this post.

Author: Mentorphile

Mentor, coach, and advisor to entrepreneurs, small businesses, and non-profit organizations. General manager with significant experience in both for-profit and non-profit organizations. Focus on media and information. On founding team of four venture-backed companies. Currently Chairman of Popsleuth, Inc., maker of the Endorfyn app for keeping fans updated on new stuff from their favorite artists.

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