Mentoring Startups is Hard: Five Ways to Be a Better Mentor


Mentoring has become a more significant part of the economy today than since, perhaps, apprenticeships in the Craftsman Age. Why? The rise of entrepreneurship and our expanding freelance economy are driving massive transformation, and workers are increasingly required to find their own means of making a living.

During the Industrial age, most labor was focused on optimizing repeatable tasks. Repeatable tasks are taught. Mentoring is more focused on developing leadership qualities, responsible for corporate management. (See Steve Blank’s blogs on Durant Versus Sloan.) Today’s mentoring must teach leadership, too, but additionally, the nature of entrepreneurship.

The requirements for high-quality mentoring have changed, but in most environments outside of major tech hubs, the practice of mentoring has not kept pace.

The successes, for example, of Y Combinator and Tech Stars can be attributed directly to the quality and rigor of their mentorship.

Of course Y Combinator and Tech Stars have access to world-class entrepreneurs and experts and I’m guessing their mentor programs have evolved as they found what worked and what didn’t. While the rest of the world doesn’t likely have the same access, we certainly can improve our mentoring and mentor programs.

Here are my five keys to successful mentoring:

1) Teach, Don’t Tell

The role of a mentor is not to criticize a business model. Too often I hear comments to founders that add up to “That’s a terrible idea” or “That will never work.” The mentor might be right. Truth be told, the mentor probably is right. But that’s not because the mentor knows this to be the case. It happens to be the nature of the beast that if you predict failure, you’ll be right 9 out of 10 times.

The role of the mentor is not to replace the founder’s business model assumptions and market guesses with his own. The mentor should teach the founders how to test and validate (or likely invalidate) those assumptions.

I recently had a conversation with the leader of a local mentoring organization who insisted that it was her responsibility to prevent founders from wasting their time on ‘bad ideas.’ This is a problem. You are not the arbiter of good ideas.

Your expertise may even be blinding you! (See more “Domain Experts” below.)

If by mentoring, you mean sitting around a table with other ‘mentors’ criticizing business models to impress each other, please find another way to spend your time.

You’re not helping.

The best mentors teach the founder skills, so that she can learn whether the idea is good or not.

 2) Focus Your Advice

Mentoring advice should be focused on … Next Page »

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Brant Cooper helps organizations big and small innovate. He is the co-author of "The Lean Entrepreneur," leader of San Diego Tech Founders, and a sought-after speaker, advisor, and mentor. Follow @

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One response to “Mentoring Startups is Hard: Five Ways to Be a Better Mentor”

  1. FastMikie says:

    This is good stuff, Brant. Thanks for posting…

    I follow your advice on following up the mentoring sessions, but put the burden on the Protégé and ask them to summarize our meetings in writing and then I get the chance to see if they really got what I hope they got out of our meeting.

    All the best,