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


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exposing non-validated assertions. It’s great that entrepreneurs are passionate about their product idea; they need to be. But conviction based on passion creates a faith-based startup that is doomed to fail.

Second, mentors can help founders devise experiments, provide introductions to customers, or come up with other ways to learn what is unknown, such as looking for analogs in the marketplace.

4) Beware of Being a Domain Expert

Sounds counter-intuitive, I’m sure. Aren’t you supposed to bring your domain expertise? In The Lean Entrepreneur, we talk about how business activities vary depending on where a particular product sits on the innovation spectrum.

Once the bastion of franchises and medium-to-large enterprises, startups do a lot of incremental innovation these days. That’s fine; big businesses are outsourcing some of their sustaining innovation. Domain knowledge is particularly helpful on the sustaining side.

But if you try to apply your industry expertise to a startup that is trying disrupt that industry, you’ve got a problem:

To industry insiders, disruptive innovation looks like bad sustaining innovation.

You might want to read that again. This is why “experts” love the phrase “It’ll never work!” That’s the last thing a founder needs is to hear from an insider.

Not that there isn’t some knowledge to be leveraged. If you can remove yourself from the emotion of seeing your industry potentially disrupted, you can share market knowledge, contacts, and other tips and hacks.

And yes, the mentee should be aware of this when seeking advice from industry experts, but also, the best mentors are those who are aware of their own biases and steer clear of areas in which they have a personal stake or an emotional connection.

5) Teach Entrepreneurs How to Be Good Mentees

I have often heard myself complaining that those I’ve mentored rarely follow up. It could be I wasn’t a good-enough mentor for these founders. But my ratings have always been high, and I also hear this often from other mentors. So many entrepreneurs also need to be taught how to be mentees. While many mentors view follow-up as a indication of “entrepreneur-worthiness,” mentors who are interested in a particular startup or founder should instead reach out themselves.

Reaching out doesn’t mean a mere “How’s it going?” Reaching out is mentoring: it’s something like, “Hey, I haven’t heard from you in awhile. If you really wish to take advantage of my (or other’s mentoring), you need to be way more proactive.” Here’s what mentors should be recommending to their founders:

—After each mentoring session, write an email thanking the mentor and summarizing the conversation.

—Follow up within a week with specific action taken on the advice or why action wasn’t taken;

—Write a monthly update on company status, needs, achievements, etc. Send this to all mentors, investors, and other interested persons.

You won’t hurt my feelings if you have chosen to work closely with other mentors, but I think the above advice will serve you well. Exceptional mentors ping the entrepreneurs. It’s related to teaching business development, so you are actually developing a skill.

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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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  • FastMikie

    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,