What makes a great mentor? Know what you don't know

We all know Mr. Smartest Guy In The Room. I find him insufferable and have nicknamed him Mr. Smartypants. Unfortunately, there are a lot of Mr. Smartypants in my world, as he inhabits the bodies of some entrepreneurs and the souls of a lot of investors. Regardless of who he manifests himself in, he’s still tiresome and when there are two of him in the room, watch out.

The best mentors are not Mr. Smartypants. While great mentors know a lot and has had plenty of experiences, they're always learning. The best mentor/mentee relationships are peer relationships, where mentors learn as much from the mentees as they teach the mentees. There’s no room in this relationship for Mr. Smartypants.

I know a lot about some things. And I know very little, or nothing about a lot more things. My business and technology experience is deep in software, where even the hardware companies we are investors in (Fitbit, Sphero, Makerbot, Glowforge, littleBits, and some others) are what we like to refer to as “software wrapped in plastic.” At the essence of it all is software, and that’s what I know best.

But I don’t know all software. And I especially don’t know vertical markets. We’ve consciously stayed horizontal in our investing, being much more interested in our themes which apply to many different vertical markets. But ask me about a vertical market, whether it be entertainment, real estate, insurance, auto, food, energy or financial services, and I’ll often approach it with a beginner's mind.

In some cases, I think something generic will apply to a vertical market. But when asked about something structural, even though I’ve had lots of different experiences, read a zillion magazine articles over the years, and might have some opinions, as a mentor I’m quick to say, "I don’t know" — unless I’m confident that I do.

When I find myself in an “I don’t know” situation as a mentor, I immediately start trying to figure out who I can refer the entrepreneur to who might know something about the situation. And just because I don’t know doesn’t mean I’m not curious about finding out more. I’ll often stay engaged and hear what the mentor has to say, just so I get the benefit of having more data in my head to play around with in the future.

I say “I don’t know,” or some version of it, at least daily. How often do you say it?