More on mentors

Last month I wrote about why you ought to find a mentor. This week I thought I’d write a little bit about how you go about getting and maintaing one. Let me preface this by the fact that I am by no means an expert but now I have at least been on both sides of the table. Lately I’ve been getting a bunch of emails from kids (many my own age) and time and time again I see the same mistakes. Many of these errors seem to be common sense to me, but I nevertheless understand the tendency to make them.

Here are a few don’ts and a few dos.

1) Don’t be presumptuous. I can’t tell you how often I am literally appalled at the balls on some people. Whatever you’re asking for, it’s probably too much, so scale it back. If it’s a question they’ll answer it. If it’s “Will you sit and listen to my life story?” you’ve crossed the line. Obviously the relationship is centered around getting something from them, but you need to space that out over time. Perception changes everything, so consider that asking for everything up front as opposed to a little advice every couple weeks could mark the difference between learning a lot or nothing at all.

2) Don’t compliment yourself. Don’t insult yourself. Both extremes are equally detrimental. They are the ultimate distraction from the issue at hand. The former, they have to (if anything at all) take you down a notch. The latter, they have to waste their precious time reassuring a complete stranger. Either option leaves you spending capital that is already in short supply. Once you’ve finished writing your email, scroll through and find out all the affirmative claims you make about yourself and delete them. Remember what Ralph Ellison said about power–that it was “confident, self-assuring, self-starting, and self-stopping, self warming and self-justifying.” It does not need to make claims, they are implied. That the issue is even being addressed says the opposite about you. And on the other end, if you’re lacking the confidence to get it done, why should someone bother putting any energy into you?

3) Don’t be obsequious. Compliments are one thing, being full of shit is another. A person worthy of mentoring you is going to be self-aware enough to realize the majority of their flaws and faults. For you to come in and pretend those don’t exist shows that you either are too oblivious to accurately judge situations or dangerous brown-noser. They want to relate to you on a real level, and that’s impossible if you approach them as something other than a real person. So it is imperative that you let them know why you respect them, but they are not the second coming of Christ–and they know it.

4) Whatever you do, do not insult them or what they stand for. I got an email a little while back where someone pretty ruthlessly insulted Tucker, and then the guy wanted something from me. Now aside from the fact that I would consider TM a friend and someone who has helped me enormously, how does it benefit anyone to insult my boss (and indirectly me for working for him)? Understand that people hold certain things to be sacred. You need to find out what those are and treat them with the reverence they deserve. Let me say this again, being brutally honest doesn’t make you stand out, it makes you a dick. If that’s the route you want to take, go for it, but people don’t often mentor dicks.

5) Stay in the picture. You are easily forgotten, remember that. The key then is to find ways to stay relevant and fresh. Drop emails and questions at an interval that straddles the fine line between bothersome and buzzworthy. Even if they don’t respond, that they saw your name again means a little. If they forget your name or what you offer them then the relationship is pretty much dead. And it’s easier to keep something alive than it is to revive the deceased. I get an email from one kid every couple weeks and it’s perfect, they are always short little emails and I almost always see through them–but at the same time, I respect the ingenuity.

6) Bring something to the table. Anything. Quid pro quo. Even if it’s just energy. Even if it’s just thanks. You cannot ask and ask and not expect to give anything in return. The bigger the payoff you can offer, the longer they’ll take you under their wing. Figure out what you can offer and actually give it. Here’s a freebie: Find articles and books that relate to their field and pass on a recommendation and then they won’t have to waste their time searching.

7) Apologize. When you screw up, more likely than not, you’ll realize you did it immediately after saying or emailing it. Don’t wait for their reprisal, or the token period of silence. They’ll forgive your errors (within reason) if you indicate a propensity for identifying them. I know when I’ve crossed the line and you probably too. Reproach can be softened by mutual understanding.

Note: If any of these things reference something you think you might have emailed me, chances are it’s not. They’ve all happened multiple times–and some of them are ones I’ve made myself.

Written by Ryan Holiday
Ryan Holiday is the bestselling author of Trust Me, I’m Lying, The Obstacle Is The Way, Ego Is The Enemy, and other books about marketing, culture, and the human condition. His work has been translated into thirty languages and has appeared everywhere from the Columbia Journalism Review to Fast Company. His company, Brass Check, has advised companies such as Google, TASER, and Complex, as well as Grammy Award winning musicians and some of the biggest authors in the world. He lives in Austin, Texas.