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Mentorship And The Art Of The Cold Email

The cold email landed WayUp's CEO dinner at Sheryl Sandberg’s house and conversations with executives at Match and Twitter.

Myriad blogs and self-help books tout the benefits of having a mentor: that person that helps guide you up your career beanstalk. But finding a mentor can often seem elusive. Perhaps that’s because looking for a single person to lead you through your career isn’t the right approach.

"I don't think anyone should have one mentor unless you have one problem for the rest of your life," insists Liz Wessel, cofounder and CEO of WayUp, a startup aimed at connecting college students with jobs. When she encounters a problem or needs advice, she makes a list of all the people that she knows might be best at solving that particular issue, then contacts each person directly.

"I'm all about cold emailing," she says while speaking with two other female founders, Jennifer Fitzgerald, CEO and cofounder of Policy Genius, and Kathryn Minshew, cofounder and CEO of The Muse, at Fast Company’s Innovation Festival. It's an intimate audience mostly made up of women.

The cold email, Wessel says, has landed her dinner at Facebook COO Sheryl Sandberg’s house and conversations with executives at Match Group and Twitter. Wessel’s endearing nature may play a part in her success, but she says her cold emails work because she carefully researches her prospective mentors.

Research That Reveals Very Specific Shared Interests

She starts with a problem that she’s facing, such as hiring a new executive or attracting better talent. Then she makes her list of people and takes up to an hour to figure out what she has in common with each of these potential mentors. The commonality could be anything from a past job to a current affinity. She highlights these similarities in the subject line of her email, which might read as "Fellow water aerobics instructor wants to ask advice" or "Person who also lived in India while working at Google wants to ask advice."

The body of the email itself, she says, should be kept short. Include your shared experience, but get right to the point and be specific about what you want. "Just don't say ‘I want to pick your brain,’" says Wessel. "That's just the most annoying thing." Instead, she says, ask them a specific question, like how to attract hot talent or how to grow your team—whatever your burning question is. Offer to take them to coffee or chat via Skype.

Look For Those Who've Been There (Recently)

Minshew echoes Wessel’s advice, but says she doesn’t just seek out multiple mentors for specific issues, she specifically looks for people who recently wrangled with her particular dilemma. "When I look back to the people that were most helpful to me in the early days of The Muse, a lot of them were six months to two years ahead." Her roster of confidantes isn’t filled with big-name executives, she says, but entrepreneurs who have just hired their first CMO, or recently scaled from 30 to 100 employees.

"Do you want to understand how to get through managing someone for the first time?" asks Minshew. "Someone who learned that skill in the last 12 months is going to be amazing at teaching that to you, in a way that a person who's been managing for five years may or may not be able to."

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