On Mentoring

Mentoring relationships are complex and tenuous, but they work best when the needs they fulfill are clearly identified. And like any relationship, they require nothing less than mutual vulnerability.

An idea came to me on the train to work. I went to Amazon.com on my phone, tapped in the name of the book I’d just finished reading,1 and sent a second copy to my former professor. Then, I wrote him an email asking him to pass the book along to a student—“perhaps a bit shy, but mischievous”—who could use it. “My email address is enclosed on an attached note,” I continued, “and I’d love to hear from the student once she’s read it.”

The book landed with a young woman named Jane Chun. I heard back from her a few months later, just before Thanksgiving. When she came home to California to visit her family, we met in person for the first time. We had so much to talk about.

After Thanksgiving, Jane and I kept up our correspondence. Every so often, one of us would revive an old email thread or send a note to say, “thinking of you.”

Our exchanges intensified in the summer of 2011 when Jane wrote to ask for advice on an upcoming interview, initiating a back-and-forth that spanned several weeks. After the interview was over and the only thing left was to wait, she sent a note of thanks: “Throughout this process you have been such an incredible mentor to me, and I really appreciate all the time you have put into answering my questions.”2

My heart surged: I’d never been called a mentor before. Jane’s matter-of-fact tone made her words easier to accept. There was no coronation ceremony—no praise to resist. Just an observation, an offhanded remark. Its straightforwardness gave it the ring of truth.

When Jane called me her mentor, it changed the way I saw myself. I was spellbound by the sense of wholeness that came from being useful just by being myself. I wanted to feel that way all the time. I wanted everyone to feel that way all the time. The invocation of the word “mentor” was the turning point for me. I thought that sharing that soaring feeling could be as simple as invoking the word “mentor” more often.

So, I started a project called /mentoring. “Anyone can be a part of /mentoring,” I wrote by way of introduction on August 30, 2011. “All it takes is a few lines of text on your own website, blog, or other profile, expressing your openness to mentoring and offering a specific invitation to get in touch.”

Tense but hopeful, itching for escape velocity, I decided to go big: “I’m calling it ‘/mentoring’ because I hope that eventually it will be as natural a part of the internet as ‘/about’ pages. I’m placing my invitation at http://dianakimball.com/mentoring, and I invite you to do the same.”

The response was immediate and affirmative. Friends and strangers tweeted and retweeted about /mentoring; a few even put up pages based on the template I’d shared. I could feel momentum building. But almost as soon as /mentoring took off, I started to have misgivings.

As reports from the field rolled in, I began to feel like I’d sent my friends up a creek without a paddle. There were the basic questions I’d only lightly anticipated: when a stranger writes to ask for advice, how and when do you transition that conversation to the phone? Once you’re on the phone, how do you take responsibility for overcoming the awkwardness and opening up the conversation in earnest? As the conversation winds down, how do you broach the topic of whether the person on the other end can expect an ongoing relationship or needs to make peace with it being a one-time thing?

And then there were more difficult questions that emerged only in practice. If it turns out that the person is, quite transparently, trying to bolster their chances at a job interview with you—as actually happened to one friend of mine—how do you bounce back from the feeling of manipulation? What if their listlessness or lack of direction seems every bit like depression, but you don’t have enough context to say for sure, and it’s not your place to say, anyway? What if what they want from you isn’t actually something you have to give?

Alarmed by the legions of awkward interactions I felt sure I’d unleashed through /mentoring, I retreated from the project after a few short months. Although the instructions for setting up /mentoring pages remained online, and many friends’ open invitations persisted on their websites—whether through willing dedication, obligation, or inertia, I still don’t know—I promoted the project less and less, and eventually, stopped entirely. What started as a movement became a liability.

The awkwardness of mentoring had mesmerized me, though, and I wasn’t ready to let go. The whole experience of introducing /mentoring and then witnessing its gentle fallout had only reinforced my belief that the word had power. I needed to understand it. So in the spring of 2012, my friend Beau Rowland and I embarked on a research project: we were going to solve the mystery of mentoring.

The more Beau and I learned, the more complicated mentoring revealed itself to be. We read about the word’s origins in Greek mythology, the challenges of setting up mentoring programs in the workplace, and the should-be-obvious-but-easily-ignored importance of setting expectations and boundaries in any mentoring relationship. And then, in a book by an organizational behavior professor, we discovered something that seemed to explain it all.

In Mentoring at Work: Developmental Relationships in Organizational Life,3 first published in 1985, Kathy Kram outlines a framework for the behaviors that constitute mentoring. She organizes mentoring behaviors into two broad categories: career functions and psychosocial functions. Career functions include sponsorship, exposure and visibility, coaching, protection, and challenging assignments. Psychosocial functions include role modeling, acceptance and confirmation, counseling, and friendship. Looking at those two lists, my mind woke up. No wonder mentoring is complicated! The term is loaded beyond belief.

Mentoring is a mess because it’s hard to know what it means. If agreeing to be someone’s mentor means volunteering to serve as a coach, a confidante, a role model, and a therapist all in one, what exactly does saying “yes” obligate you to do? The person asking to be mentored could mean any number of things; they might not even know what they seek. And when you think about it, that’s not surprising at all. How often can any of us name what we need?

Needs are holes; they’re hard to talk about. Before you can put words to your needs, you have to learn to see negative space. I didn’t recognize how difficult or important this was until I stumbled across a book called What We Say Matters,4 by Judith and Ike Lasater. “Learning how to identify our needs and how to get them met is a fundamental life skill,” they write. The book’s view of needs is broad; the authors refer to the work of Manfred Max-Neef, who named nine basic human needs: affection, creation, freedom, identity, participation, protection, recreation, subsistence, and understanding. Identifying and filling those needs as they arise is the work of a lifetime.

Critically, identifying needs and filling them are two separate steps. In What We Say Matters, the authors draw a distinction between needs—the gaps in our lives that reveal themselves through patient introspection—and strategies—the ways we bridge them. To illustrate the difference between needs and strategies, they use the example of love:

If I have a strategy for getting love from a specific person and that person does not give it, I am stuck without getting my need for love met. But there are always many strategies for getting any particular need met, and so it is with love. I can get love from many other sources in my life. Viewing love as a need frees me up to search for another strategy to get that need met.

In my experience, the impulse to find a mentor usually comes when something’s missing. But what? The tough love of a coach, the steady attention of a trusted confidante, the motivating proximity of a role model, the probing questions of a therapist, or something else entirely? Figuring that out would already constitute a major step in the direction of self-knowledge and potential satisfaction. As the authors of What We Say Matters point out, “if you ask for what you want, you’re more likely to get it.”

Yet the disentangling doesn’t have to stop there. Tough love, steady attention, motivating proximity, and probing questions can all be seen as strategies for meeting even more basic needs: to be challenged, to be understood, to be inspired, to learn. Finding a mentor can be one way to meet those needs, but it’s not the only way. Remembering that there are other ways can serve as a release.

It’s good that there are other ways, because mentoring is a tenuous thing. For mentoring to work, the stars have to align such that two people need each other at a moment in time. Mentoring relationships are relationships first and foremost, and relationships are forged through mutual vulnerability; anything less is a dead end. Those who seek mentoring need all kinds of things. But the figures on the other side of the equation often appear enigmatic from the outside. When people decide to act as mentors, what needs are they trying to meet?

When I decided to act as a mentor, what needs was I trying to meet?

The year I met Jane was a hard one. A sudden death in my family had thrown me, just after I’d started a new job in a new city. Through twelve months of self-doubt, I spent a lot of time reading on the topic of “how to be a person”—very much the genre of the book I finished that fated morning on the train to work. When it occurred to me to send the book to my former professor and ask him to pass it along, the creativity and generosity of the idea came as a surprise. Creativity meant my imagination was working again; generosity meant I felt strong enough to help others. Being there for Jane was a significant step in my own recovery. What I needed was to get outside of myself.

Not every mentor arrives at a willingness to help out of a desire to mend. Just as often, the ease and joy of mattering carries the day. Sometimes, the urge to be inspired by someone else’s aspirational energy comes into play. There are countless needs that mentoring can meet. The important thing is to make sure at least one need is alive in you, and to at least try to give it a name.

Looking back, the biggest problem with /mentoring was my assumption that what was true for me when I started the project would remain true forever. Simply adding the page to my website met my need to feel like someone with something to give. Encouraging others to do the same met my need to make a difference in the world at large. For a moment in time, everything lined up.

Yet as time went on, inbound mentoring requests rarely arrived when I was prepared to receive them. People poured their hearts out in letters, as I had asked them to. But since their letters arrived on their own time, I wasn’t always ready to reciprocate. And without the click of mutuality, most of those would-be relationships fizzled out before they began. If I agreed to speak with someone through the frame of /mentoring but couldn’t bring myself to be vulnerable in exactly the moment we spoke, the conversation went nowhere. One-way vulnerability—from them to me—became about power, not closeness.

Power dynamics are an unavoidable part of the idea of mentoring. One person is experienced, the other aspiring; one person is giving, the other seeking. But the best mentoring relationships subvert that power dynamic. In fact, all good relationships play with power dynamics. Status games are an important way of showing affection. In the book Impro: Improvisation and the Theatre,5 Keith Johnstone explains how this could be:

Many people will maintain that we don’t play status transactions with our friends, and yet every movement, every inflection of the voice implies a status. My answer is that acquaintances become friends when they agree to play status games together. If I take an acquaintance an early morning cup of tea I might say “Did you have a good night?” or something equally “neutral,” the status being established by voice and posture and eye contact and so on. If I take a cup of tea to a friend then I may say “Get up, you old cow,” or “Your Highness’s tea,” pretending to raise or lower status.

When we’re comfortable enough to shift between high and low at will, laughter and epiphanies erupt. Freed from the expectations of knowing everything or knowing nothing, we can get closer to the truth together. It’s why I asked my professor to introduce me to a student who was “perhaps a bit shy, but mischievous.” I wanted to meet someone who could hold her own. I wanted to help, but I didn’t want to be held to a rigid standard; I wanted to be myself.

To be acknowledged as a mentor in hindsight is meaningful because it is a form of thanks. To be asked upfront to be someone’s mentor is unnerving because it’s a boundless request, an inchoate please. The word has power both ways. But if we set aside the word and go back to basic needs, mentoring starts to look like something much simpler: friendship. Of all the possible outcomes of mentoring, the best one is ending up on the same level.

So it was that one day in June 2013, Jane showed up at the apartment my boyfriend and I shared in San Francisco. I was moving to Berlin and needed help like nobody’s business. She knew this, and decided to pitch in as part of saying goodbye. Jane surveyed the kitchen, clapped her hands, and began. Together, we bundled cups and bowls in bubble wrap and talked about our days.

  1. Tina Seelig, What I Wish I Knew When I Was 20 (HarperOne, 2009).

  2. Personal correspondence with Jane Chun, published with permission.

  3. Kathy Kram, Mentoring at Work: Developmental Relationships in Organizational Life(University Press of America, 1985).

  4. Judith and Ike Lasater, What We Say Matters: Practicing Nonviolent Communication (Rodmell Press, 2009).

  5. Keith Johnstone, Impro: Improvisation and the Theatre (Routledge, 1987).

Diana kimball

Diana Kimball is a writer and reader. She graduated from Harvard Business School and was part of the original team behind ROFLCon. She also co-founded 24-Hour Bookclub, an occasional reading flash mob. Diana now lives in Berlin, where she listens and works at SoundCloud.

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Illustration by Matthew The Horse · Portrait by Richard Perez