It’s not what you don’t know that will hurt you, it’s what you don’t know that you don’t know

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Years before Dick Cheney made famous the concept of the “unknown unknowns” (U2s), a business partner of mine identified this as a key problem for entrepreneurs – like us. What we didn’t know we didn’t know about venture capital, for example, would have filled several books back in 1989. Unfortunately for us there were no books about venture capital and we definitely didn’t know what we didn’t know. Fortunately for us we were taken under the wing of MIT’s treasurer, Alan Bufferd, who managed the Institute’s investments and who taught us some of the basics of venture capitalism while accompanying us on our first visit to Greylock – a VC firm MIT invested in and who ended up being the first and only investor we talked with. Greylock ended up investing over multiple rounds in two of our ventures.

The article What startup mentors can learn from family doctors by Prasanna Krishnamoorthy taken from LinkedIn, has a rather misleading title, but has some excellent advice for both founders and mentors. A study of startups at Microsoft and Upekkha in India discovered that founders were unable to take advantage of all-star mentors. Why not? Evidently they found was that “unless a mentor deeply understands the founder and startup well, most advice is too shallow.”

After studying the problem the conclusion was that “mentoring is about helping a founder know their “unknown unknowns.” So the role of the mentor becomes helping founders help with deal unknown biases, blind spots, and gaping voids that are invisible to the them. Having been a mentor for going on 10 years I have to admit to a) never having thought of mentoring in this way and b) never having heard this explicit mandate from any of the many organizations I have mentored for. But here’s the catch: in order to do this successfully a mentor “needs to spend eight to 12 hours with a particular founder.” That’s totally unreasonable and family doctors don’t even spend 10% of that time with their patients.

However, one way to approach the problem is to have a series of deep discussions with founders focused on finding their unknown unknowns. This requires regularly scheduled meetings totaling anywhere from 10 to 20 hours. Frankly even this is beyond most mentoring groups I’m aware of, as mentoring is either usually on-demand (when the founder calls out for help) or lightly scheduled (once per month). But let’s assume the mentor and founder can set aside this amount of time. Incubators and accelerators can be exceptions to this rule, which may account for the success of Y-Combinator and TechStars.

First founders have to prioritize their U2s. Next they needed to create specific problem statements around these U2s. That enables mentors to identify subject-matter experts who can assist with these very specific problems. This process creates a very efficient process for the mentor. In fact at MIT VMS a subject matter expert is often brought in to help with an identified problem beyond the ken of the mentor team. One case the author mentions is not unlike cases I have had myself: founders who were using direct sales but had no idea how to build an inbound/inside sales team and what processes the team would use. They then crystallized the problem statement to “create the core inbound process for lead-gen in the next six weeks,” and connected them to an alumnus who is among the best in India at inbound marketing.

So  what are the takeaways for startup mentors?

  1. Understand the startup’s context and constraints.
  2. Try to enumerate their major problems.
  3. Help the identify their U2s and their blind spots
  4. Help prioritize their problems.
  5. Get them a subject matter expert to help with domain-specific problems like marketing or customer support.

How can a founder take advantage of good mentors?

  1. Identify areas you believe your mentor can help with: where they can provide feedback and where they have a network.
  2. Do your homework! Start each meeting with an agenda (which should be sent out in advance) and then report on the status of the homework.
  3. Work with your mentor to identify blind spots, weaknesses, and biases.
  4. Make sure each meeting ends with a recap of action items and summarize them for the team (founders and their mentors) (This is standard practice at MIT VMS).
  5. Circle back to the mentor with the outcomes, positive or negative, from the actions.

Mentorship is obviously now a worldside best practice for startups and we can learn as much or more from mentoring in India as we can from the U.S., and we hope, vice versa.

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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