A Darker Side of Mentoring

I asked my 7-year old daughter for the first time the other day, “What do you want to be when you grow up?” For some reason or the other this particular question had never surfaced in our many previous conversations (and she is quite gregarious, taking after me, as has been observed—which is not necessarily a compliment).

She replied rather uncertainly, and after some thought. “I want to be a doctor.” Something in her eyes sought my approval.

“A doctor? That’s interesting. Why a doctor?”

Again that uncertain tone, making a statement as if it were a question. “Because I want to help people?…”

“Oh really? Ok, so why would you like to do that?” I was adopting a casual conversational tone in much the same way as I would in asking her which bedtime story she would like me to read her before bed.

“Oh!”  Deep thought, and then more confidently she replies, “Actually, I don’t want to be a doctor.”

“Ok. Why not?”

“Because I am not interested in being a doctor.”


“Actually, I would like to be a pilot!” she exclaimed. And so the conversation continued.

I realized that this is a conversation that many a parent and child may have, but the reaction of the parent would determine the outcome. For instance, if I had responded to her “help people” quaver with a big smile, maybe a hug and a statement of how proud I was of her noble and altruistic motives, perhaps I might have gotten a different response. It is quite likely that she would have picked up on this fondest of parental ambitions for their children (i.e. to be a doctor) and the predictable canned response (i.e. to help people) somewhere: perhaps at school, from her friends, whispered in her ear by grandparents etc. How easy it would have been to yield to that ambitious parental desire; but how tragic might have been the possible outcome. We would never have known or even suspected that she had no desire to be a doctor—a fact that I may later explosively confront with her years later as she may give up on medical school, and in my opinion, having wasted those sacrifices I may have made for the extra coaching sessions, the ‘enriched’ streams in school curriculum, MCAT prep-school, the obsessions with grades, the greedily amassed ‘volunteer’ hours interning at hospitals, and all the other paraphernalia of getting her into med-school, and all for the simple and inconsequential reason that she didn’t want to be a doctor.

How does this domestic scene shed some light on our workplace interactions? Even in the most wonderful of scenarios where a boss does indeed have the best interests of the subordinate at heart, and most particularly in the case where a rising star has a been taken under the wing of the benevolent boss, so to speak, we see a variation of this scene play itself out. Think of that famous relationship between John Sculley and Steve Jobs, where so many parallels could be drawn to the father-son dyamic, which is just one of the many mentoring relationships that go awry. Even if one were to cast a glance at more commonplace occurrences that have surprised many a benevolent manager when a liked subordinate suddenly ups sticks and moves to a competitor. While the experience holds true for increasing numbers of women, the male pronoun still dominates the comments: “I always thought he was happy here” or “He had a great future here” are common comments that come from head-scratching managers, if they are not completely exploding at the ‘betrayal’ by that snake-in-the-grass whom I treated…ahem, like a son.

These relationships have a way of being heavily dependent on those first originating conversations, where under the benevolence of mentorship, the promising new talent is groomed in the image and expectations of the mentor, but often not of the mentee. The disappointed mentor may often exclaim “Why didn’t he just tell me? I would have listened! We need not have wasted this time and energy!” It is never easy to “just tell” and even more so when the mentee cares deeply about the impression made on the mentor, and appreciates the care and attention given by the mentor. Finally the ‘telling’ will have to happen, the dread the mentee feels having to finally come out with the ‘truth,’ the sense of betrayal the mentor may feel, the recriminations and the forever damaged relationship. I can look back on such moments from my youth and early adulthood as a mentee (and son), and in my later years as a mentor (and father). I can blame myself, my mentors or my mentees, but that does not break this potentially vicious cycle.

Or I can become more conscious of those originating conversations and of how much I am shaping the conversation or being shaped by the conversation. To return to the metaphor of the parent and child with which I started this entry, I can anticipate a possible objection from many an ambitious parent that “I know what is best for my child! I am looking out for my child’s best interests in the future!” which may very well be true, but then one should not be too surprised if the child confounds the parent’s expectations, or back in the business world if the mentee confounds the mentor’s expectations. I cannot offer to my daughter an opinion on the virtues of a career as a doctor or a pilot, but at least I know now what she wants, and more importantly what she does not want… and that is a start.

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