An Unorthodox Guide to Mentoring

Forget what you’ve always been told about how mentoring arrangements should work. Here’s one woman’s unsparing look at the pleasures and perils of the workplace’s most complicated relationship.

Mentors are the Holy Grail for working women. We desperately seek them out, believing they’re our helpmates to the top. We look to trail-blazing women; we curry favor with powerful men. I’ve spent half my adult life seeking out teachers, and, looking back, I have to confess that even from the best I acquired no more than so-so help.


I think women — and men — have to stop looking for advice outside of themselves. There is a story about the remarkable George Ivanovitch Gurdjieff who, among other things, is considered the father of scenario planning. When he was a young man, Gurdjieff would go out on his porch with an armload of books to read in the long summer afternoons.

Invariably, one of his neighbors would come out on his porch and start whistling and humming. Gurdjieff tried to read through the annoyance and found after a few weeks that he’d been so distracted that he’d been daydreaming rather than concentrating on the wisdom in the pages in front of him. Thank goodness, he concluded. If I’d read those books I might have filled my brain with useless information. By daydreaming, he came to hear his own thoughts.

Secondhand learning — advice — is overrated. Before you learn what others know, you need to learn what you know. My search for mentors came to an end when I got to spend a day with a man still considered a mentor to thousands. After a discussion that was so confusing I couldn’t follow a word he said, a photographer came to take our picture. I was told to sit at the great man’s feet, and he stood behind me. Waiting for the camera to go off, he farted. Right in my ear. You take revelations where you can get them. That moment summed up for me the true value of mentors.


So, here’s my unorthodox guide to getting and making the most of your own guides:

To Learn, Teach

Women typically feel they need to be “credentialed” to claim authority. I’ve found that the worthwhile things that I learned in life I taught myself. I learned the finer points of grammar as a high schooler coaching elementary-school kids; I learned as we went. I used to mentor authors in how to write books long before I’d written one. Find someone whom you can mentor on the subject you want to learn. You’ll learn faster and indelibly.

Give Help, Don’t Ask for It

If there is someone whose knowledge you need, offer to help her. You’ll find yourself in a trusted position and in a role in which you are not treated as a second rate “mentee,” but as a peer.


If You Must Ask for Help, Be Discreet

An ambitious young woman confided that she was going to invite a recently promoted colleague out to lunch to “tell her I want her job and ask her how to get it.” I shuddered at the thought. This young woman should instead ask the colleague whom she most admires about her five-year plan, for example. A direct question, journalists know, always puts a source on the defensive.

Watch, Don’t Talk

Mentors are everywhere; you don’t have to sign someone up for the role. If you start watching how people do things, you’ll find people tacitly noticing that they are being observed. Often they are flattered by the attention and start teaching and including you.

Try the Polish Generalissima’s Paradigm

Two women in the Polish military made a secret pact: They decided to help each other rise in the hierarchy. Whenever Magda went to a meeting, she’d be sure to work praise of Theresa into the discussion. Whenever Theresa wrote a report, she recommended Magda for new responsibilities. Before long, third parties were saying, “I hear Theresa is brilliant,” or “Magda is being considered for x position.” Both rose in the hierarchy simultaneously.


Dig Your Well Before You’re Thirsty

This old saw bears repeating. Cultivate relationships with important people before you need them. Send cards, notes, or things you think will be of interest and ask nothing in return.

Male Mentors Require a Safe Distance

I’ve had great male mentors, but when I look back, I realize that I underestimated what they took from me: I paid them in spirit, enthusiasm, help, self-understanding, and empathy far beyond the value of any advice they gave me. Spend yourself wisely. Don’t take promises as payment. Make sure the deal is reciprocal. Don’t ever underestimate what you have to give. And don’t give more than you get.

Don’t Look for Praise; Look for (Gentle) Criticism

Praise reinforces what you know; criticism forces you to learn more.


Don’t Despair If You Don’t Have a Mentor

Two of my heroes, Jackie Kennedy Onassis and Eleanor Roosevelt, never had mentors. They would never have limited themselves in that way. They engaged the best teacher in the world: namely, the world itself. Jackie read constantly and even in her tender twenties knew so much that she became the source that created Camelot, one of the most powerful political myths ever invented. Roosevelt was a committed student of literature and history. Each triumphed based on what she taught herself, not on what peers or mentors had to offer.

Know When to Fold Your Tent and Leave

There always comes a time when you have to cut off a mentoring relationship. What looks like help can turn into a case of psychological abuse when the mentor, demanding more mirroring or praise, stops giving. Or when you’ve learned all he or she has to offer. At that point, say good-bye before the relationship turns painful.

Harriet Rubin ( is a Fast Company senior writer and author of The Princessa: Machiavelli for Women (Doubleday, 1997) and Soloing: Realizing Your Life’s Ambition (HarperCollins, 1999).