Mentorship: Here’s My Selection Process

A few weeks ago I opened up the doors to mentoring companies. I couldn’t possibly have been prepared enough for the enormous response. It’s both humbling and terrifying.

The first thing that I had to do is come up with a process by which I decide whether or not I scribble on the metaphorical dotted line. I’ve played this out a few hundred times in my head, and it’s come down to a very specific set of questions that I have to ask myself.

1. What Can I Offer?

It would be very easy to accept every request that comes across my desk. But if I do this then I’m going to run out of bandwidth quickly, and I won’t be doing a very good job for anyone. So I start my process by looking at where the company is right now, and seriously considering whether I have a set of skills or knowledge that can help them. If I don’t, then I immediately thank them for their interest and explain in detail why I don’t believe that I’m the best choice for their goals.

2. Am I Conflicted?

This one’s a bit more tricky. Thus far I’ve had everything from Android apps to daily deals marketplaces in my email. The hazard here (for one example) is that I seriously dislike the daily deals system, and so I know that I can’t be a good mentor to them unless we’re talking about completely changing their approach to their business. Sometimes that’s a viable option. More often than not it isn’t.

3. Who’s Behind It?

I believe firmly in the TechStars and Y Combinator method of investing in teams who do great things. I’m investing time, rather than money, but time is a valuable asset to me. Ideas can change. The people behind them are less likely to do so. I request a story from every person on every team that I mentor. I want to know who they are and what they do, not just their idea.

4. What’s the Timeline?

In many cases I’ve had companies who have simply needed a bit of help prior to an investor pitch or demo day. These are easy. An hour or so on Skype and things are pretty much finished. But other times I have people who are still in the idea stage of a project that could literally be a hundred-year company. I have to do some soul-searching to figure out how much time I can offer them, and whether it’s mutually beneficial to start that relationship.

5. Where’s the Love?

Sometimes it’s the team. Other times it really is the idea. But there has to be a near-tangible connection in order for me to work with someone. If I don’t love them or their idea, why am I going to waste their time? Maybe the idea is genius, and perhaps it’s being put together by the verifiable best people in the world. But without a connection it’s just a power grab and that’s the wrong way to approach mentorship in my opinion.

There you have it. These are my five questions that I ask every single time. There are others, of course, but they’re perhaps less frequent or more specific to the situation. I’d love to hear from other mentors to see what I’m missing, because I’m sure I don’t have all of the answers.


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