Then, at a certain age, many of us become mentors ourselves. In fact, those of us in positions of leadership are often thrust into the role of mentor, whether we like it or not.

For the past 40 years or so, mentors have become a staple of office life, or at least office jargon. (We’ll skip the earliest appearance of Mentor in Homer’s Odyssey and later mentions in 18th century treatises like the Marquis Caraccioli’s “The True Mentor.”) In the 1970s and ’80s, “mentor” became a verb, and permutations like “mentoring” and “mentee” entered the language. Scholars have cited the publication in 1978 of The Seasons of a Man’s Life, a book by psychologist Daniel Levinson, as an especially influential event.

Today, most organizations genuflect to mentoring—more than two-thirds of Fortune 500 companies have some sort of mentoring program in place.

Among those who took naturally to guiding others was Peter Drucker. Inc. magazine went so far as to call him “the North Star of mentors,” saying that Drucker’s “generosity of spirit and his accessibility have surprised the raft of executives who have sought his counsel over the years.”

2

RECOGNIZE THAT MENTEES CAN BE FLAKES

On the face of it, mentoring arrangements look like they’re liable to sink or swim based on the availability and focus of the mentor. After all, the more senior person may well make a commitment but then fail to find the time to follow through.

In reality, however, it’s often the junior colleague who flakes.

“It’s usually the mentee who gets busy and doesn’t understand how important this is,” says Katy Dickinson, a consultant who created and for a decade managed mentoring programs at Sun Microsystems (now part of Oracle). An article in the Journal of Management Education echoes this point, maintaining that many mentees “lack the motivation, discipline and know-how to make the relationship work.”

At times, Dickinson adds, mentees may find themselves simply overwhelmed with everything they’re being taught. “It may take them several years to process what they have learned,” she says.

For a senior executive, this can all be frustrating, even galling. But don’t be too hard on your mentee. Have you always matched your teacher in devotion? How well did you, at age 25, truly understand what was important and what wasn’t?

“The biggest trap managers can fall into is wanting the development to happen more than the individual wants it himself,” says Carol Walker, who worked at the insurance company Chubb and the investor communications firm CCBN.com before launching her own management consultancy. “The mentor must ensure the mentee truly owns the process. Action plans should be initiated by the individual being mentored. Follow-up meetings should be driven by that same individual.

“If ownership is clear,” she explains, “the mentor can generally avoid this pitfall.”

3

SET CLEAR EXPECTATIONS

“Ownership” isn’t the only thing that needs to be clear. So should your expectations about what mentees are supposed to do to ensure success.

What kind of development plan do you want them to create? How will you know if they’ve followed through? If you don’t expect them to carry out a formal action plan, what exactly do you want them to learn—and how will you know if they’ve really absorbed those things?

If your company has an official mentorship program, look to your HR colleagues to help you set the parameters of your relationship. “We did not throw people together and say, ‘Have at it,’” observes Sheila Forte-Trammell, who until she retired a few years ago was the leader of the global mentoring program at IBM.

Yet even if your HR department provides only minimal support, it’s incumbent on you to monitor how your mentee is faring. “If you don’t collect data on how the relationship is going in the first couple of weeks,” Dickinson warns, things can quickly fall apart.

4

DON’T GET BOGGED DOWN BY STRUCTURE

While expectations should be clear, remain flexible. The best mentors know when to stray from the script.

“Too much structure takes away the spontaneity and creativity and innovation that two people can bring to it if they’re not in such a regimented program,” Rose says.

Rick Jensen, vice president and chief talent officer at Intuit, the financial software company, notes that the organization offers a variety of development programs for employees. Generally speaking, though, mentoring is encouraged informally rather than formally. “You can create a very clinical experience,” Jensen says. “But leadership isn’t clinical.”

In Jensen’s view, mentoring shouldn’t be confined to weekly or monthly appointments. “When I need mentoring, I need it in the moment,” he says.

8

BE READY TO LEARN YOURSELF

Some organizations recognize that it’s younger workers who have something to teach their older colleagues—new social trends and technologies, for example. That’s why Jack Welch famously set up a “reverse-mentoring” program when he was chief executive of General Electric.

But even in the absence of this kind of initiative, your mentee should be putting you in touch with your own organization, giving you an ear to the ground at a point in your career when you may be operating at a remove. If you’re ready to drink it in, you may well take away the most in terms of new knowledge.

“In some ways, I think that the older employee can be even more ripe for learning and adjusting their behavior,” Rose says. “When you hear about mentoring programs, they focus on the young person, but such an exclusive focus hasn’t been my experience at all.”

10

DON’T BE AFRAID TO GET PERSONAL

Even an exquisitely structured mentoring program is dependent ultimately on chemistry.

James Hayden, a partner at the New York law firm White & Case, has been a mentor to younger attorneys—so impressively that his efforts were chronicled in Harvard Business Review.

“What I learned about mentoring … is that it’s as much a personal as a professional relationship,” Hayden says. “To work it must be based on all of the elements that work to create friendship in relationships outside the workplace.”

A true mentor is comfortable, when appropriate, taking a business relationship beyond business. That was the experience of Bob Buford, a cable-TV pioneer and social entrepreneur who in the early 1980s decided to seek out a consultant by the name of Peter Drucker.

“I was not necessarily thinking friendship but simply about success,” Buford would later recall. “A few sessions with Peter Drucker would surely help me uncover ways to grow my business by a few more percentage points.”

What Buford got in the bargain was far more than he expected: a mentor who left him “enriched beyond any measure I could have imagined” and who “cared as much for me as a fellow human being as he did for me as a young, ambitious entrepreneur.” So close did the two men grow that Drucker was among the first to call when Buford’s son died in an accident at age 24.

As in all the best mentoring relationships, the affection and esteem went two ways. “I cannot even begin to tell you what your confidence in me and your friendship has meant for me,” Drucker wrote.

If you’re ever able to pen such a letter yourself, you can be totally confident that you’ve been one heck of a mentor.*

Additional reporting provided by Paul Bisceglio

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