1) Folks are forever asking me how to approach a mentor. The simple advice: take a loose connection and slowly build on it. Most of my mentors were grounded in a shared connection (same college, b-school, worked at the same company, shared interest in skiing, sailing, biking)
2) In shaping a loose connection into a tighter relationship, recognize there has to be some sort of personality fit. You have to like talking/interacting with each other. That takes some light emails/coffee/casual meetings over time.
3) Then be aware of the potential mentor's "tests". They are time-starved and will test you a bit. LIke, "If you'd like to talk more, set up a meeting two months from now." The test there is to see if you will remember to do it, and can navigate their crazy schedule.
4) Mentees forget this, but part of the job of a mentee is to bring value to the mentor. It's a lot easier than you think. In my case, I love feedback on my writing/talks/exec events and I make it super easy via my surveys. A clever few include their email with their survey fb.
5) There's lots of ways to create value for a mentor. Mentors are typically older and fear becoming irrelevant & you can help them to stay in touch. My Stanford students, for instance, helped me to understand that a Prius is, in fact, "bougie"-- I thought only a Tesla was.
6) Please, please don't start by asking a person, "Will you be my mentor?" That's a DOA approach. Start with a very specific "ask" like, "I noticed you've developed expertise in online learning and I am curious If I could compare notes on Teachable as an online platform?"
7) The specific ask starts things slowly and everyone likes the subtle compliment that they're good at/expert in something. They just have to answer one question, not sign up for a long-term relationship.
8) Frankly, the biggest reason that folks don't reach out and establish mentor relationships is most folks are afraid to ask for help. In asking for help, and acknowledging the potential mentor's expertise, you've got a 10-20% shot that the relationship will form, over time.
8) Build from there. If you find ways to build ongoing value, pass the mentor's tests, and build the relationship, the mentor-mentee relationship may advance, over time.
9) Some subtleties. A lot of relationships will form out of a networked relationship. Learn how to participate in a two-sided intro. (Look it up: I recall Hunter Walk doing a very specific "how to.")
10) The line between persistence & overly persistent. Most folks make the mistake of not being persistent enough. You'll get their attention via persistence & good luck (they see your email come in at 5 am) but also via your ability to demonstrate potential value to them.
11) The folks that are comfortable with candor will say "no thanks" but most will ignore your approach until you tire. But there's a lot of middle ground in there. Expect success in 10-20% of the cases which is why networked approaches and loose connections are so important.
12) Summary: Build on loose connections, find ways to create value for your potential mentor, be vulnerable enough to ask for help, start with a small, very specific "ask," pass their "tests" and be very persistent. And, please, please don't start with, "Will you be my mentor?"
