Over my ten years of mentoring at MIT and elsewhere I’ve worked with a large number of other mentors, as both the MIT Venture Mentoring Service and the MIT Sandbox Fund employ team mentoring. Teams can range from two to as many as five or six.
Every mentor has a different mix of experience and expertise. What we all have in common is that we have been screened by the VMS or Sandbox management and we all agree to adhere to the code of ethics.
What I’ve observed is that there are two basic modes or styles of mentoring: prescriptive and Socratic. The prescriptive mentors tell the founders what they should do – their mode is instructive or didactic. Their advice is usually clear, concise, and quite directive. Socratic mentors, such as myself, ask questions, which we believe will lead the founder to examine his or her options and the pros and cons of each. We focus on decision support, not making decisions for the founder.
Both VMS and Sandbox have very short time horizons: mentors focus on what founders need to accomplish in the next month or two, not the next year or two. Advice is usually quite concrete, not abstract, and next meetings are predicated on achieving agreed upon milestones.
No mentor is 100% prescriptive nor 100% Socratic. Occasionally I will be quite directive if I believe the founder needs to do something or they may suffer negative consequences. Often these situations are legal issues, such as trademark, copyright or related intellectual property matters. My advice is these cases is “Book time with the VMS legal mentor or BU Law Clinic ASAP!” Conversely even the most prescriptive of mentors will ask a clarifying question or two before instructing the founder on a course of action.
What can be challenging is when you have only two mentors on a team and one is directive and the other non-directive. The poor founder’s head is on a swivel and I can see confusion set in. At such times I’ll try to reframe the prescriptive mentor’s directive into a question to give the founder a chance to reflect and think about the advice being given.
Mentors provide advice, guidance, feedback, perspective, and support. My goal is to help founders succeed in pursuing their goals. But it often takes a number of questions to actually find out what those goals are! Reviews and feedback on a presentation is perhaps the simplest mentoring exercise, while providing advice to a founder having problems with a colleague is the most difficult. But my interim goal in helping a founder to succeed is to get them to think. And to think about their options, the pros and cons of each and most importantly, the repercussions of following one option versus another.
Founders tend to have a bias for action, but sometimes the most important advice I can provide is, “What a minute!” Usually followed up with a question, such as, “Have you thought about X?”
If you are a founder in a mentoring relationship it would serve you well to learn to recognize these two modes of mentoring. You can respond to the highly prescriptive mentor with your own questions, such as “Why are you recommending that course of action?” “What are my other options?” “How do they compare with your choice?” Conversely when you find yourself subject to a series of questions from a Socratic mentor you might ask them to pause and say something like, “What would you do if you were in my place?” “I need to make a decision now, can you give me more specific advice?”
Of course, the most important mentoring skill is neither asking the right question at the right time nor recommending a single course of action you deem best. It is listening. And listening needs to be active, not passive. Active listening is comprised of four elements:
- Concentrating fully on the the listener – don’t start thinking about your response while your founder is still talking! Pay attention to body language. Are they leaning forward or backward? Looking relaxed or tense? Speaking rapidly, softly, or loudly?
- Understanding – don’t assume you understand. Check with the founder. Ask him or her directly, “Is this what you mean?” or “Could you clarify or amplify that?” or “Here’s what I hear you saying, am I correct?”
- Responding – the key is that your response be relevant and helpful. Be concise. The best advice is actionable, as founders are always under pressure to decide their next step.
- Remembering – if need be take notes, but make sure you keep track of what has been said, how you responded, and if the discussion seemed to help the founder or not.
While having an undergraduate degree in psychology is mildly helpful to me, I wish I had taken a course or two in counseling, negotiation or conflict resolution. However, most mentors have learned our skills from our own mentors or observed other mentors in action. Given the prevalence and importance of mentoring I would like to see a course dedicated to the best practices in mentoring entrepreneurs.
In the meantime, mentors should be aware of their style and consider modifying it when appropriate. And that’s about as directive as I’ll get!
Mentorphile 
And you could be part of putting that course together! Your writing is so clear and compelling, even for “civilians.” LB
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