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Answer by Gayle Laakmann McDowell, founder and CEO of CareerCup; author of Cracking the PM Interview, Cracking the Coding Interview, and Cracking the Tech Career; former software engineer at Apple, Google, and Microsoft:
You don’t ask someone to be your friend, so why do you ask him or her to be your mentor? Think about your closest friends—or even your less close friends. When you asked them to be your friend, what were your terms? How often would you hang out? What would you do? What would the expectations be on each side?
Oh, you didn’t do any of that. You didn’t ask them to be your friend. That would be weird. Plus, how would they know if they like you before they know you? It’s a sort of ridiculous question to ask or answer.
But somehow or other, you just … became friends. Maybe you just “fell” into friendship by hanging around each other enough. Maybe there was something specific that connected you, like having children the same age. Maybe someone introduced you two because you just moved to their city. Somehow or other, nothingness evolved into friendship.
Like friendships, mentorships—the ones that actually exist, not the ones that exist in name only—rarely start from a formal request and certainly not from a near stranger. It doesn’t work for mostly the same reasons. It’s artificially trying to create a personal relationship. Doesn’t work.
Moreover, with many mentorship requests (especially those between strangers), the more junior person is often not actually committed to making it work. If you’ve never sought out my advice before, why do you think you’re now going to want to regularly get it? More likely, you suddenly thought: “Know what I could use? A mentor.” Your interest will likely wane.
Let’s be honest: neither of us are likely to follow through with this mentorship, even if we both intend to. If you want someone to be your mentor, don’t ask him or her to be your mentor. Let it build (or collapse) authentically. That doesn’t mean you can’t seek out mentorships. You can, just like you can friendships. They’re not all that different. Both are fundamentally personal relationships, even if one is forged over drinks and gossip and another over coffee and advice.
To establish a mentorship:
Make yourself not a stranger. I recognize the names of people who regularly comment on my Quora posts, who share my Facebook posts, and who retweet my tweets. If I feel like you’re not just a total stranger, I’m more likely to help you.
Write well—no text-speak or sloppy punctuation. I can absolutely forgive grammatical mistakes caused by being a non-native English speaker. But if you’re adding spaces before periods or not capitalizing words (or Capitalizing random Words), that’s just being lazy and unprofessional. If you’re lazy and unprofessional, I’m unlikely to try to help you professionally. Why bother, if you’re not doing what you can to help yourself?
Get to know him or her—in person. An online connection just isn’t the same. Make it really, really easy for the other person. Find out where he works or lives and meet him nearby. Offer to buy him coffee; it’s not about the money. It’s about establishing that you value their time.
Be persistent—but only a little. I get a lot of emails, and, much as I wish this weren’t the case, I don’t respond to all of them. If this relationship matters to you, follow up. For the most part, I don’t refuse to respond to emails. I just haven’t yet gotten around to yours yet (and I might never).
Make her like you. If possible, do something for her. The vast majority of mentorship requests I get are from people who have read one or more of my books but haven’t posted a review on Amazon. Look, I’m an author. Reviews are a big deal. If you tell me you love my book and you’re asking for help from me, I’m likely to think, “If you love it so much, why not post a review?” I recognize I’m being a little unfair here—the prospective mentee probably hasn’t really thought about posting a review. But, still, I’m a lot more likely to help those who I feel are willing to help me. I’ll feel a bit indebted to you, and I’m more likely to help you. In fact, if I even see signs that you’re generally a nice and helpful person to other people, I’m more likely to help you. I prefer to help nice people.
If I know you (even a little), if I feel like you’re trying to help yourself, if I feel you’re a nice person, and especially if I feel a little obligated, I’m a lot more likely to chat with you—especially if you make it really easy for me. We can see where things go from there. We don’t need to establish terms and conditions, so please don’t ask me to be your mentor.