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.

An Illuminating Blackout

On the afternoon of July 5th 2010, most of the people who worked in Toronto’s downtown core were somewhat discombobulated by a power failure. Once its cause was identified (transformer caught fire), and implications assessed to be relatively trivial (90% power restored in 3 hours), most people were given the rest of the day off, though some of them had to trudge down 30 stories of stairs as the elevators were not functioning. This incident did have an ominous antecedent, the massive power failure across the North America’s Eastern Coast in August 2003. It also provoked a sigh of relief: say for instance, what if the power failure had happened during the G20 Summit which was just the week before? Whatever one’s views of the Summit or of the global economy, such a power failure could have had quite unexpected outcomes.

Nicholas Nassim Taleb’s wonderfully engaging concept of Black Swan events (unpredictable, massively gamechanging, and post facto rationalized) obviously comes to mind. His basic argument is that future events are not predictable, so (from a business perspective) our naïve belief in the risk assessments of various models gives us a false sense of security until a massively game-changing event occurs. The black swan events can be negative e.g. the 2008 economic crisis, or they can be positive e.g. the rise of Google. The key issue I want to raise here is that of risk, and specifically in the context of business, where it is assumed to be brought under human control as much as possible.

The advanced research in Physics, Economics, Mathematics (and even in emerging sub-disciplines like Chaos theory) are brought to bear on the science of managing risk. The rewards are great and the reassurance of the science employed gives us, one and all, a sense of confidence that the risk is indeed being managed. One of the first big principles I studied in Finance was the difference between market risk (the spread of risk among all investments in the market), and unique risk (the risk associated with specific investments). The name of the game has become one of managing this latter type of risk through judicious portfolio management, but rarely does one (in a non-academic setting) consider the implications of the ever-present systematic risk. It is usually represented as a uniform band, probably because it recognizes the existence of less than perfect markets, exogenous conditions like black swans, which by being slight and rare respectively do get very thinly spread out over a large volume of transactions and extended period of time. But, to pursue this metaphor of risk being ‘spread out,’ presumably as butter is spread out on a slice of bread, the problem is that the topography of risk is not as smooth as a slice of bread; it is a combination of smooth plains as well as steep cliffs and deep crevasses. It is these exogenous, Non-quantifiable. Non-measureable, and largely undiscoverable species of risk that completely wipe out any risk-mitigating strategies that may have existed prior to their unexpected incidence.

How, for example, would Bear Stearns have been able to insure themselves against the actual risk associated with the mortgage-backed assets that ended up taking down the company? On a broader economic front, one could argue that it is precisely this sort of fear of a black swan event that would put such a massive fear into the minds of people’s disposition to invest, which would ironically end up crippling the economy: no one would want to transact business out of fear of that huge, unknown and unexpected risk. And they would be right. However, the ‘huge, unknown and unexpected risk’ is not mitigated: we can simply push that into a corner of our mind as we place more faith in calculations, analyses, reputations, novel financial models, and soon amidst all the paperwork, the excel sheets, the models—not to mention the deliberate book cooking, socialization of losses and privatization of gains—we have managed to take a junk bond and work it up to a triple A rating. The risk is not mitigated, it is just swept under the carpet.

Why does this happen? Being more familiar with human behaviour than with the complexities of finance, I would hazard a guess that it stems from a need for control. The market risk is so uncontrollable; the unique risk on the other hand yields itself to measurement, is affected by endogenous factors, and can be spread smoothly over efficiency frontiers (assuming a normal Gaussian distribution, a smooth and well-mapped topography of risk). Therefore when the one firm (or the one portfolio management team), wants to distinguish itself from the others, it seeks the people who will be able to make a difference in the areas that can be controlled, hence the physicists on Wall Street and the superstar financial consultants. As this controllable aspect of risk (unique risk & its predictive models) becomes more and more the differentiating factor between competing individuals, the ante gets upped, and the war for talent reaches unprecedented levels. Meanwhile, the really significant black swan type risks are safely ignored until it is too late and all hell breaks loose—as it did in 2008.

The most recent Toronto blackout is therefore a reminder that the world is not as predictable as we expect. Sometimes unpredictable events happen and have consequences. Yes, we all know that, and yet we get out of bed each morning and get on with the business of the day. The value of the reminder lies in never forgetting how much of the real impact of risk is exogenous, unquantifiable, unpredictable. That sobering consideration tempering our decisions and actions as we carry out the business of the day may well be our last defence against the market risk that threatens…well, the business of the day.

Taleb’s “Ten Principles for a Black Swan Robust World” Financial Times. April 7, 2009 is a short, entertaining and provocative recommendation. <http://www.fooledbyrandomness.com/tenprinciples.pdf&gt;

Thinker’s Arithmetic

In 1784 in Germany, a seven-year old boy, Carl, was enrolled in a typical public school, one of those old schoolhouses where hundreds of poor pupils of varying ability congregate, and are taught by a disagreeable teacher whose primary tool of instruction was the liberal use of his whip: something out of a novel by Charles Dickens. The class was asked to sum all the numbers from 0 to 100, while the teacher probably settled at his desk for a nice long snooze as the pupils patiently pencilled away.

How would one usually approach this problem? Precisely the way that most of the students did:

0 + 1 + 2 + 3 + etc.

Carl, however, discomposed his teacher by announcing a few seconds later that the answer was 5050. He noticed that the numbers formed pairs of 100 i.e. 0 + 100 = 100, 1 + 99 = 100, … 49 + 51 = 100 to a total of 50 pairs. Then there was the single median number 50 which did not form a pair. Now the summing was easy: 50 pairs of 100 makes 5000, plus the median 50 makes 5050. From this simple arithmetical example, we can learn how new ways of seeing can substantially change our preconceived notions of approaching problems. Carl went on to become Carl Friedrich Gauss, one of the greatest mathematicians in history. But is this sort of revelatory insight only reserved for the geniuses of the world? I think not.

Having been a teacher and business coach for many years, I have seen similar moments of insight in my students. Thinking may start with a random thought or observation, but then one needs to grasp that thought and examine it: What does it imply? When is it true? When is it false? How can it be tested? What significance does it have to the problem at hand? In short, we start with a thought and we probe it, sift it through our experiences and learning until it gets converted from a mere thought to an insight. This is thinking.

One of the best ways to think is through the writing of my thought processes. Writing helps me ground my thoughts: they are right there on the page for me to recall, elaborate, modify and hopefully to illuminate. Consider how many interesting casual observations you make in the course of each day. If you were to pick just one of them and spend about 15 – 20 minutes writing about it, sifting through it, and mentally working through it, you have a journal, a record of the idea. Presumably in a class of over a hundred students there must have been at least one other pupil who noted the multiple pairs that added up to 100. Carl, on the other hand, thought through the observation until it yielded an insight. You doubtless have many thoughts and observations each day. Pick one, think through it, and write through it. Every day then becomes a day of discovery.