Six things a good mentor shouldn’t do


jenn labin

Mentoring is one of those activities with a very low bar to entry. Frankly anyone can call themselves a mentor, though fortunately for founders, most accelerators, incubators and academic entrepreneurship programs do screen their applicants for mentorship. So if you are finding a mentor through one of those established channels you can be assured that they are probably experienced founders at the least and have some experience as mentors as well.

But there are no hard and fast rules for mentorship; each organization seems to have its own guidelines. When you realize that virtually all mentors are volunteers you can understand whey their parent institutions are loathe to be too directive for fear of losing their volunteers. But fortunately the web has a lot of material about how to be a good mentor and also how to avoid doing a poor job as well. I’ve tried to aggregate many of these articles at Mentorphile.

Fast Company has a helpful article in this vein by Gwen Moran entitled These are the six things the best mentors never do. sub-titled Mentoring is tough. Get better at it by avoiding these common missteps.

The article is based on advice from Jenn Labin, founder of T.E.R.P. Associates and author of Mentoring Programs That Work.While Jenn Labin’s focus is on career mentoring, not the mentoring of entrepreneurs, these six things to avoid are just as applicable to those of us who mentor founders.

I’m going to list these things the best mentors never do, with my comments below each one.


Jumping to conclusions is something not only mentors but founders should never do! In fact my advice to my teams at startups has always been, “Minimize your assumptions.” Mentors should also be on the lookout for mentees who jump to conclusions. As the old saw goes, “Look before you leap.”


Mentor meetings usually range from 60 to 90 minutes. With that limited amount of time it’s very important that the meeting be managed carefully. The best way to do that is to request that the founder send an agenda in advance of the meeting. Then the first order of business should be to review the agenda, make any additions or deletions, and decide in what order issues should be addressed. As someone who has to plead guilty to having meandered or watched as others meandered, I know it is all to easy to go off on tangents, and then tangents to tangents. Putting the agenda up on a whiteboard in plain view of everyone is one way to keep the meeting on track. However, I wouldn’t be totally rigid on this one. Occasionally you can meander into a topic, like an issue in the founder’s personal life that is making his work situation particularly challenging. As the saying goes, “If you don’t know where you are going any road will take you there.” Keep the founder’s objectives for the meeting in mind at all times. And it helps to periodically check in by saying, “Is this discussion helpful to you?”


This refers to the need to followup. The most important notes I take at any mentor meeting refer to commitments I have made to the founder, typically to make an introduction or a referral to someone in my network. And it can help a great deal to followup on referrals, sometimes the smallest things, like a mistyped email address, can prevent a successful connection. Don’t assume you have successfully connected your mentee to someone, double check with them.


Founders are often outnumbered by mentors, so don’t make it even more difficult for them by being overly directive or domineering. The best antidote to this is asking questions instead of making statements. And when dealing with a thorny issue it can be helpful to preface any advice you give with, “As I understand it from you ….” Because sometimes you will not understand it!


This is one item I just don’t agree with. Who will have a hard conversation with a founder if not their mentor? This is particularly true before a venture has raised any capital. Recently I had to have a hard conversation with some founders who seem to be avoiding drafting a founders agreement. I asked them point blank, “Is this a hobby or is it a business? If it’s just a hobby then it won’t be a problem not having a founders agreement. If you intend to build a business you need a founders agreement and you need it now.” I’m glad to say they responded positively and my only regret is that I didn’t have this hard conversation about what was preventing them from creating a founders agreement earlier. But no harm, no foul.


What Jenn Labin is referring to here is resisting a change in the relationship. As ventures grow they and their founders do change. Mentors may need to change their approach to the founder. Advice given to a pre-revenue company will differ greatly from a company generating revenue. Just as founders need to be flexible, mentors must be also.

Mentoring is not a one-way street; it’s a relationship. Relationships evolve over time. At some point the founder may have a board of directors and even a board of advisors as well and it may then be time for the mentoring relationship to phase itself out.

What all these points have in common is that they demand self-awareness on the part of the mentor. You need to monitor your own behavior, what you say and how you say it, just as closely as you monitor your mentee.



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.

One thought on “Six things a good mentor shouldn’t do”

  1. I really liked that piece. Underlines for me how complex mentoring can be.

    Thank you for the help this AM.

    See you around dinner time.



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