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Younger and Wiser

Why you should seek out mentors who have less life and career experience than you.

Finding a mentor can be a fraught affair, both for would-be mentors and aspiring mentees. If you’re prime mentor material, someone who holds a senior position and commands respect, chances are you’re inundated with requests. And if you were to accept half the mentor requests you receive, you would barely be able get your work done. As one senior female executive I know lamented, “Every time I step out of my office, I’m practically ambushed with requests.” In Lean In, Facebook chief operating officer Sheryl Sandberg reported being similarly crushed.

The imbalance between supply and demand gives rise to another set of problems. Since the most prestigious mentors are probably oversubscribed, you may feel foolish pestering people with your entreaties. Being rejected can make you feel as if you’ve signed up for a bad dating service, with the added indignity of having to encounter the person who rejected you on a regular basis. And yet every time you turn around, someone’s thrusting research (pdf) in your face showing that people who succeed are those who have managed to engage the right mentors. So the quest to find the perfect mentor remains at the top of your inexhaustible to-do list, causing perpetual low-grade worry.

Organizations often try to address the mentor gap by instituting formal programs. While these can be helpful, effective mentoring thrives on chemistry, which is hard to mandate and does not necessarily respond to assignment. It can work but it can also feel generic, awkward, and dutiful.

There has to be another way.

Paul Smurl may have found one. After working as an attorney and management consultant, Smurl held a range of positions managing online products, strategies, and subscriptions for the New York Times for nearly 12 years. He ascended to the role of acting head of digital in 2014. In 2015, Smurl surprised colleagues by leaving to take a position as president and COO of Some Spider, an Internet publisher founded by e-commerce star Vinit Bharara. Some Spider owns the popular parenting site Scary Mommy and has restarted the topical satirical site Cafe.

After making this gutsy move, Smurl knew that breakthrough success would require new skills, fresh insights, and an expanded way of viewing the world. The Some Spider demographic skews fairly young, which meant that Smurl, nearing fifty and married with children, needed to sharpen his understanding of the next generation’s media habits.

“It goes beyond technical proficiency,” he says. “I can use and consume Snapchat and Yik Yak but I don’t naturally live there.” The challenge he faces when it comes to new messaging technologies isn’t technical — it’s strategic. Everyone in the media business has to be able to grasp the implications of how communications is evolving.

So, like anyone looking to up his or her game, Smurl needed a mentor. He ended up turning to Kareem Rahma, a former colleague from the Times who had worked in audience development. Kareem is now CEO of, a social media startup that offers original video content along with chat functionality. A 2008 graduate of the University of Minnesota, he is also decades younger than Smurl.

The relationship started when Smurl asked Rahma out to dinner, not to “pick his brain” — a request that makes most of us shudder — but rather to exchange ideas. Their conversation proved rich and helpful to Smurl and they began meeting regularly. “I didn’t so much need advice as I needed context,” Smurl says. “Kareem helped me get it.” He’s explicit about considering Kareem to be a mentor.

“For example, the other night we got together and he was telling me how his users have begun exchanging content with messaging tools, like Facebook Messenger, instead of broadcast tools that post to your whole network like Facebook,” he says. After they talked at length about the implications of this shift from broad to narrowcasting, Smurl decided to start testing messaging applications at Some Spider.

Prestige shouldn’t be the marker that determines a mentor’s potential value. Rather, people should simply consider “what can help.”

Based on his experience, Smurl advocates engaging younger mentors. Prestige shouldn’t be the marker that determines a mentor’s potential value, he says; rather, people should consider “what can help.” Of course, having a mix of mentors is ideal. In addition to offering lessons in management and in life, older mentors tend to have long-standing relationships that can be helpful. But given the extraordinary four-generation range of people in organizations today, from 20-something millennials to 70-year-old matures, and the fact that digital natives possess a bred-in-the-bones feel for how technology is driving change, there can be real value in thinking outside the age-frame box.

How can you make December–May mentorship relationships work? Smurl has three suggestions for those intrigued by this route.

1. Be self-aware. “Start by taking an honest audit of your strengths and weaknesses and decide what you need to work on,” Smurl says. “I knew I needed to understand emerging media from the perspective of an engaged and passionate user, so I looked for someone who really was.”

2. Don’t take a transactional approach. “Being a good mentee is basically Human Relations 101,” Smurl says. “You need to be interested in the other person.” In his experience, most mentoring relationships fail because the mentee sees the mentor as a means to an end –– it’s all about advancing his or her own career. Such an approach does little to foster the easy give and take that fruitful engagement requires.

3. Recognize that mentoring should be a two-way street. “Even as you’re getting help, consider what you can do to help the other person,” Smurl says. “For example, I have relationships I’ve cultivated over many years that can be useful to Kareem.”

Though mentoring connotes sharing your wisdom or insights with someone else, if you never perceive a benefit to yourself, you will eventually lose motivation. In Smurl’s view, formal mentoring often founders because the incentive is all one-way. The desire simply to be magnanimous can make mentoring gratifying, but it’s likely to pall when things get really busy. At its best, mentoring is mutually beneficial, no matter what the mentor and mentee’s respective ages.

Sally Helgesen

Sally Helgesen is the author of seven books on leadership, most recently How Women Rise: Break the 12 Habits Holding You Back from Your Next Raise, Promotion, or Job, coauthored with Marshall Goldsmith. She delivers workshops and keynote addresses around the world and has been a contributor to s+b since 2005. 

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