The right advice

Having a mentor seems like such a brilliant idea that many people fall under the illusion that it’s an easy process, and assume everyone will jump at the chance to offer career connections and advice for free. Yet it’s actually harder to land a good work guru than a good marriage partner.

Luckily, having multiple mentors is easier than having multiple marriages, and you can approach, court, and juggle several guides simultaneously.

But before you ask anybody for assistance, beware. Feeble attempts to network, charm and cajole luminaries can lead to humiliating blunders. Here are some careful, canny, and classy ways to coerce someone older or wiser into promoting you professionally.

1 Real life isn’t a reality show: Chances are Donald Trump won’t invest in your real-estate scheme and Oprah won’t invite you on her show to push your book. It’s smarter to start small, focusing on admirable individuals already in your world—a kind boss, esteemed co-worker, nice neighbor, successful older relative, compassionate doctor or teacher.

2 Approach only those you admire: Don’t indiscriminately target anyone rich or famous in your field. If you don’t honestly think highly of someone and try to fake it, you’ll come across crass and phony.

3 Act entitled, get deleted: Unless you’re calling your uncle Dave or your mom’s college roommate, be humble and understated, assuming you’ll have to earn the ear or energy of higher-ups.

4 Be prepared: Before making contact, make sure you Google, go to the library, read the book or see the movie of the person you’re targeting. The more you know about their business, the better. The harder you work, the luckier you’ll get.

5 Enough about you: Don’t begin a letter, e-mail or phone conversation, “As a recent honors graduate who doubled-majored in political science and philosophy” and then list your accomplishments. On some level you’re implying, “I want your job, your salary, and your life.” So have the brains to begin by praising your potential mentor’s accomplishments. A former boss of mine says if the first contact starts with three “I’s” the answer is already no.

6 Don’t demand too much too soon: Imagine asking a cute stranger, “Will you go out with me every Saturday night for the next three years?” That kind of overkill will make you look needy and insecure. Keep initial requests small and non-threatening—a handshake, a signature on a book or program. Build up to bigger favors.

7 Don’t be a stalker: Don’t show up at someone’s home or place of employment without an appointment. A better approach is a fan letter or e-mail briefly expressing your honest appreciation. Include your phone number, address and e-mail in case they decide to respond.

8 Connections connect you: If you know someone in common, say it in the first line. If you don’t have a direct in, try an indirect one. If you both graduated from the same school, or are from the same state, mention that. Or go hear the person give a lecture or reading and start by saying how much you enjoyed it.

9 Don’t trash yourself: Don’t say, “Though I’ve been rejected every time I’ve sent out my résumé…” Self-deprecating humor is dicey with someone you don’t know. Be conscious of your fears and tendency to reveal too much, tell off-color jokes, and other methods of self-sabotage.

10 Issue proper invitations: By all means offer the luminary you are approaching a speaking engagement at your class, company, or convention, or extend other offers that pay the person homage. Especially if real payment is involved.

11 Show up, shut up, ante up: The person who has the least power in any relationship has to compromise and come out of himself most. If you’re on the side seeking advice, sympathy, connections or praise, know that your guide will have the upper hand. Expect to travel to his or her turf, show up bearing presents, offer to treat, supply transportation, listen more than you talk.

12 Return the favor: Older, powerful people need young blood for fans, assistance, and to keep current. So pay back someone’s kindness with whatever power you eventually attain. Mentors, like elephants, have endless memories, and there’s no time limit to reciprocal generosity.