Thoughts on Mentoring

Mentoring is an artform.  As a newb mentor for the Techstars Cloud program, a mentor in life, and a borderline know-it-all, I know I’ve said some really stupid things to mentees.  But, I’m trying to get better.

The folks at TechStars have a mentor manifesto here.  While they asked for suggestions in the comments, I have too many to fit:

  • **Mentors don’t teach.  **Mentoring is about helping people learn what they don’t know they don’t know.  It’s best to point people in the right direction so they can figure it out for themselves.  Those are the most powerful lessons anyway.
  • Be OK with being orthogonal.  In other words, it’s fine to question fundamental assumptions that an entrepreneur may have made or to find yourself looking at a business problem in an entirely different way.  That, fundamentally, is why it makes sense for entrepreneurs to talk to everyone about their problem to get as much information as possible.
  • Customize your mentoring by the recipient.  Asking questions is the best way to learn what they need to know and how you can help.  
  • If I find myself doing all the talking, then I know I’m doing it wrong.
  • Avoid presenting your thoughts as advice.  Gestalt-based mentoring is best.  What does that mean?  Everyone has opinions but experience is the most powerful form of advice.  Instead of saying, “You need to fire that person as quickly as possible,” it’s much more powerful to explain a situation in which you learned the hard way that if someone is a problem employee, you need them out as quickly as possible.  (This is straight out of Entrepreneur’s Organization ( training.)
  • Be aware of “mentor whiplash.”  Especially in environments where a person has multiple mentors like TechStars, they’re likely to get contradictory advice.  That’s OK.  I often ask, “Hmm.  What else have you heard on this issue?” not to cheat but other people’s thoughts may help me understand better.
  • “Let me think about that and get back to you” is OK.  This isn’t Jeopardy.  Research and follow-up is OK.
  • Pre-meeting preparation is a good idea.  If possible, ask mentees to give you information ahead of time.  That way you can prepare your thoughts ahead of time.  You can also take advantage of your subconscious as it’s been proven to help with problem-solving to sleep on it to let your mind go to work.
  • Focus on quality over quantity contributions.  You’re likely have to 50 suggestions during a mentoring discussion.  As a mentor, I put myself on an “idea diet” and communicate only 2 or 3 suggestions during any given interaction.  While you’re likely mentoring a very smart person, they’re also human and can only digest so much.  Your idea diet will also increase the quality of your mentoring.  Better to share two A-level thoughts, than 50 A’s and B and (probably) C level insights!
  • This is supposed to be fun.  If you’re enthusiastic about a team and idea, then that increases the likelihood of success and a rewarding experience.
  • Silence is the only successful substitute for brains.  

The above is, of course, subject to change as I mentor myself into a better mentor. Introspection is a bitch:

The world is made for people who aren’t cursed with self awareness.  – Annie Savoy, Bull Durham (1998)

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