The five best ways to use a mentor

In Posted March 05, 2012

Over the past five 5 years I have had the pleasure of being a mentor for a number of accelerator programs and early stage start-ups.  I am about to start mentoring another batch of TechStars, SeedCamp, and 21212 entrepreneurs, and it got me thinking about who I have enjoyed working with and which founders have managed to extract the most amount of value from me.

But first a disclaimer: just because Tisch, Reshma, and Marcelo asked me to be a mentor, doesn’t mean that I know anything at all about the business that you are about to build. My views are random reflections based on learning that I have had building products and companies, and my pattern observations on user/founder behavior.

Now here are my five tips to get the most out of your mentor:

1. Get introductions

The easiest value extraction you can get from any mentor is introductions to people who would normally not take your calls or answer your emails. Most mentors get a bit of a kick out of sounding important and will name-drop a bunch in the first few meetings with you. Be prepared by having a notepad ready to jot down the names they drop. Then after the meeting, do your research, find out which of the names you can actually use, and send an email to your mentor that they can easily forward. Your chance of getting introduced to high-level people is proportional with how little effort is required of your mentor to make them.


2. Specific learnings

Many mentors have a hard time accepting that the best direction for you might be different from their journey to success. So, I find the best way to tackle this is not to have too many open-ended feedback sessions. Don’t ask “How can I improve my UI?” but be more precise and tailor your feedback request to your mentor’s past experience,. e.g., “When you launched your company you went for an invite-only launch strategy. What were your key learnings from that?” or “In your e-commerce site, which credit card clearing providers have your tried and why did you decide on X?”


3. Staying at the top of their minds

Most of your mentors have busy lives and won’t be thinking of you if you don’t force them to do so. So make sure to write interesting, easy-to-compute, weekly updates so you at least once a week get to the top of their mind share. I find that slightly pushy entrepreneurs get more out of me, and I don’t mind them being a bit pushy if they just accept that I’ll ignore their requests if I have to too much on my plate. The smart ones also remember to talk up their mentors when they meet other people in the industry. It’s an easy way to use vanity to make your company the center of conversation.


4. Emotional support

One thing that few people tell you before you start your own company is how to manage all the anxiety you will get feel in the early days of building your company. As a founder, you will be worried about a ton of things and you will have very few people who you can vent your concerns to. You don’t want to tell your investors because you don’t want them to be worried about your business; you don’t want to be too worried in front of your staff because you probably just got them to leave great jobs and you don’t want them to feel bad about that decision; and you should not reveal all your worries to your partner, because they really are already supporting you way too much. So if you don’t have a good co-founder who you have known a long time, a good mentor can be a good emotional wingman. Pick a mentor who has actually built a company from scratch and they will be able to both sympathize with and support you when you get to the dark days of being worried about what the hell you are actually doing. (Trust me, those days will come.)


5. Pick the right mentor for the right things

Many of the mentors you will meet have never actually build built a company like yours. They will be lawyers, corporate entrepreneurs, or investors. So when you choose what mentors to work with, make a small map of where you think you are weakest and make sure you map your mentors onto that. They will all try to give you advice on your product, which is ironic as it’s often the area where their advice will be weakest (especially the ones who have never built start-up products before). Make sessions with different mentors so you can focus the conversations on problems that you will need to solve besides product brainstorming, e.g., the best way to fundraise, brainstorming about who to hire and how, short-cuts to distribution, and so on.

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