A VC’s questions mirror those of a good mentor


John Lilly, a partner at the venture capital firm Greylock Partners.
Credit Earl Wilson/The New York Times

One doesn’t often think of VCs as mentors, especially when most fund one or two companies out of 100 or more they see each year. If I recall correctly, the year Greylock funded my first company they only funded two companies out of a 1000 business plans the firm reviewed that year.

However, the way John Lilly of Greylock interviews CEOs of companies has some significant similarities to the way I interact with mentees.

He’s interviewed in The New York Times: John Lilly: Simplify Your Message, and Repeat Often.

I’m going to quote him at length here, highlighting and annotating the points he makes that are relevant to mentoring:

You spend a lot of your time meeting with C.E.O.s to decide whether to invest in their companies. How do you assess them?

One is sort of a context-free assessment, which is, who is this person and how do they behave? The other is a contextual assessment, which is, am I any good for this person? There are some amazing C.E.O.s who I just don’t know how to interact with because of stylistic differences. [I’ve found very few founders who I couldn’t interact with, but perhaps because those who come to the the mentoring groups I work with are ready to be mentored.]

I ask a lot of questions, but I almost don’t care what the questions are. When people start talking about their business plan, I’ll say, “What about this, what about this, what about this?” [Unlike John, I do care what the questions are, in fact I have a standard set, including “What keeps you up at night?” “Who are your early adopters?” and “How will you acquire customers?” But I do proceed like Mr. Lilly once founders start talking about their business plans.]

You start to expand the scope of the questions to try to see two things. One is the quality of their thought process. And the other is how they interact with you. Do they become defensive? Do they become aggressive? Are they listening?

You’re trying to get a sense of whether, in a complicated situation with a lot of things going on, can they be honest and candid and still get to a productive place. Sometimes you get honest and candid, and sometimes you get antagonistic or defensive.

[While the following paragraph doesn’t relate to mentoring it’s a great comment on how VCs differ from founders – one of the best I’ve ever seen. Of course, they way I see it a VC’s job is to maximize the return of a portfolio of companies to the limited partners in the fund. A founder has just one company to focus on and he or she usually has a lot more skin the game than any limited partner in a venture capital fund.]

The one thing that’s profoundly different about being a V.C. compared to an operator is that V.C.s talk a lot about FOMO — fear of missing out. You turn things down all the time, and you worry, what did I miss and what did I get wrong? As an operator, you focus 100 percent on what you’re doing. As a V.C., you wonder what you’re not doing. It’s a difference in perspective.

See my post What’s FOMO and how it can work for you.


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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