Issue #4 | March–April 2015



Inc. magazine once called Peter Drucker “the North Star of mentors,” saying that his “generosity of spirit and his accessibility have surprised the raft of executives who have sought his counsel over the years.” But for most people, being a great mentor is neither easy nor straightforward. Lots of mentoring relationships go nowhere, devolving into halfhearted interactions that quickly flame out. With that in mind, here are 10 principles for being a better mentor, offered by executives who have been successful in such a role: Ask more than you answer. Recognize that mentees can be flakes. Set clear expectations. Don’t get bogged down by structure. Reach outside your department. Encourage the building of a board. Get buy-in from the top. Be ready to learn yourself. Know when to say no. And don’t be afraid to get personal.


Early in our careers, many of us are eager to find a mentor to encourage, support and guide us through the wilderness of life.


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.”


The Drucker Institute’s Phalana Tiller visits the Gaithersburg, Md., offices of Sodexo, which uses three fundamental principles to guide its mentoring program.


Allan Golston of the Gates Foundation, shown here, notes that mentors must be conscious of modeling behaviors.

Drucker himself credited two of his first bosses—one at a financial firm, the other at a newspaper—with being ideal mentors in their own right. “They were totally un-permissive and demanding. And they did not hesitate to chastise me,” Drucker recalled. “But they were willing to listen to me. They were sparing with praise, but always willing to encourage.”

If any of this sounds easy or straightforward, don’t be fooled; it’s not. Lots of mentoring goes nowhere, devolving into halfhearted interactions that quickly flame out. The complexities of the mentor-mentee relationship do not easily lend themselves to numbered rules in an office manual.

Nevertheless, many mentoring relationships—whether formal or informal—also succeed. What do these successes have in common? We spoke to people involved in such experiences and have come up with 10 principles for you, as the mentor, to keep in mind.



The instinct of many mentors is to swoop in and lay out all the answers for their callow charges. But the best of them push and probe, rather than pontificate.

“People learn more when they’re more active, when they come up with the ideas themselves,” says Jan Rose, a partner at AchieveMission, a San Francisco-based nonprofit that offers leadership consulting, coaching and training to others in the social sector. “The purpose of the mentor, the value of the mentor, is to listen hard, and to guide questions so that there can be self-discovery.”

Remember, too, that when you do want to give more direct guidance, the best way is to do it by example. If it’s at all possible, show rather than tell.

“There are few things more powerful than modeling,” says Allan Golston, who oversees the Bill & Melinda Gates Foundation’s efforts to help U.S. students graduate from high school prepared to do college-level work.




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.

The biggest trap managers can fall into is wanting the development to happen more than the individual wants it himself.

Consultant, former executive at Chubb and

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 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.”



“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.



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.



The former General Electric CEO is credited with pioneering the concept of “reverse-mentoring.”



Mentoring can have similarities to apprenticeships, in which a master passes on specific skills to a pupil. Some of the most effective pairings, though, stretch across departments or functions.


Doing so can reduce potential competitive conflicts between mentor and mentee. It can also help open the mentee’s mind. “When you link and cross-pollinate, you create a fertile ground for diversity of thought,” says Forte-Trammell, who made “breadth” a major focus of the mentoring programs at IBM.

The benefits of this approach don’t flow in just one direction, either. Mentoring someone outside your normal area of responsibility is a great way for you to be exposed to new ideas, as well. “In today’s workplace, skill expiration is rampant,” Forte-Trammell says. “In cross-pollinating, you’re broadening your knowledge rather than just holding onto your specialty.”



Although you want to cultivate a deep one-on-one relationship with your mentee, urge him or her to find others to also lean on for advice and feedback.

Certainly, having such a “personal board of directors” makes sense in a world in which your mentee—and you yourself, for that matter—may not be with the organization for too terribly long. “With changes in direction, restructuring, downsizing, acquisitions, mergers and, of course, recessions, your mentor is just as likely to move on or be laid off as you are,” Priscilla Claman asserted in Harvard Business Review.

Vicki Amon-Higa, who headed up leadership development rotation programs at the software company Symantec and the hospital system Sutter Health, advises everyone—even seasoned leaders—to have a personal board.

She has one herself. “These are the people you can reach out to help you get where you want to go,” Amon-Higa says.

Others, including management thinker Jim Collins, also favor a board setup. These should be “people selected not for their accomplishment but for their character,” he says. One twist, according to Collins: “Your personal board does not always need to know they’re on your personal board.”



Your colleagues, including those in the C-suite, are apt to applaud your mentoring young people in general. But once they see it pulling you away from other duties, they may well be less enthusiastic.

“Most organizations become quite undisciplined about people development in the face of financial or productivity challenges,” Walker says. “So the first thing that distinguishes successful mentoring organizations is a commitment to truly valuing and rewarding mentoring behaviors.”

Even informal mentoring requires leadership support. Golston credits his mentor Patty Stonesifer, who headed the Gates Foundation until 2009, with consistently exhibiting and encouraging nurturing behaviors. Even in organizations with formal systems in place to support the development of their talent, leadership buy-in is necessary to make it work.

“I’ve seen organizations where you have those enablers, but leadership wasn’t aligned with it,” Golston says.




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.”


Bob Buford started out simply seeking business advice from Peter Drucker, but their relationship evolved into a true friendship—a key aspect of the best mentoring.



Even if you’ve been an excellent mentor in the past, there may well be moments in your career when you should refrain from diving back in.

Every executive goes through patches when they find themselves too preoccupied with a big project or crisis to be a very good sounding board for anyone else. That’s probably a time when you should find a well-suited peer to take your place as a mentor. “I leave it to mentors to self-select,” says Dickinson.

Others, meanwhile, may never quite be good fits as mentors—and they shouldn’t be shy about admitting that. All of us have different strengths, but not everyone has the temperament and altruistic instincts to be a great mentor. “It’s always easier to select the right people than to change the way they work,” says Amon-Higa.

Ford Harding, who has long studied “rainmakers,” says it’s only natural to want to turn these wonder-workers into mentors. What organization wouldn’t want their protégées to learn how to emulate them and bring in outsized shares of revenue?

But most rainmakers, Harding cautions, are lousy teachers. For starters, they are generally too busy making rain. In addition, they tend to do a lot of their work on the phone, making it hard for a mentee to peel back what’s really happening. Rainmaking techniques also vary from person to person, yet each rainmaker tends to think his or her way is the only way.

Finally, Harding says, rainmakers can be unduly impatient: “They forget that they were once at the stage their mentee is at.”




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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Monday Mandate*

What will you do on Monday that’s different?


A great way to begin your relationship with a mentee is to share Peter Drucker’s classic essay, “Managing Oneself,” which asks people to identify their strengths, how they learn and best perform, and their values.


If you are a corporate executive, look to be a mentor at a nonprofit—or vice versa. You will be able to provide a new and valuable perspective for your mentee, and rejuvenate yourself in the process.


The next time you are with your mentee, be sure to hold your calls and don’t check your email. You have been given a tremendous trust. It’s important that you act like it.