On Mentoring

Kyle Downey
4 min readFeb 27, 2022

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One of the recurring themes running through my professional life has been mentoring. Others have written probably more cogently than I can muster about the difference between mentorship and sponsorship, and it’s sometimes framed in a way that the latter could be taken as always more valuable. It is true that sponsorship is rarer and takes more effort: I sponsored one person for over a decade, and probably the best example in my own experience the relationship was nearly as long and arguably was the single biggest factor in finally making it to Managing Director. There were times when I had multiple mentees at various levels but the scale of investment in sponsoring someone means you really cannot do it well for more than one or two people at once.

However, there is an element of sponsorship vs. mentorship which can get overlooked. Sponsoring, to a greater or lesser degree, is a two-way street. There is value to the sponsor as well as the person being sponsored in the relationship, and in fact that’s part of what strengthens the engagement — depending on the person and their situation, it can even be an expressly political act, with the sponsorship advancing the more senior person’s agenda in some significant way. In short, you cannot get away from the transactional aspects of this relationship. This does not make it wrong, but viewed in contrast with mentoring it highlights what is for me the paradox of mentoring: it is, on a certain level, a deeply irrational act.

Almost all of the value in the mentoring relationship flows from the mentor to the mentee. It takes time and energy, and though it exercises some of the same coaching muscles you ought to be constantly applying with your direct reports, that could equally be viewed as a distraction: if a big part of your job is coaching, why would you invest in teaching someone outside your area? Helping out for the greater good of the organization is one thing, but leadership is all about choice and application of limited resources. Why this choice? Why not put more energy into a team lead in your area instead, or perhaps a star executive you wish to sponsor? And looking at my own experience, the “greater good” argument doesn’t hold water: I have mentored people from other companies as well as students who found me through our alumni network. This is very, very strange if you view the world through a purely transactional lens.

Confronted with irrational behavior, you can do one of two things. You can dismiss it as a human foible, or you can look for a deeper justification for why we do something that on the surface appears to be contrary to our interests. In the case of mentoring, I think the latter is better; some irrationality should be embraced. Mentoring is an act of faith: not religious faith, but in the broader sense of the things people do in the absence of evidence that it’s worth doing, even to the degree where obtaining evidence is impossible. In humanity’s defense, when history has ended at last, our lawyers will surely mention the times we did the right things for no good reason and ask the judge, can you wholly condemn a species animated by such hope?

It is never easy to ask for help. To receive help knowing it is impossible to repay the person can border on the unbearable; perhaps, on some level, we cannot entirely believe the world is not transactional in the end. This is a debt. It must come due sometime, no? And if not, what are we to do with that? Yet we do this all the time, on both sides of the bargain. The alumna donates to her college years after leaving, and funds a scholarship for a young man who will never know her. A manager offers a reference to a colleague he will probably never work with again. We hold the door, and walk away. In matters big and small, we rack up social credit and spend it, and the connection between the lender and the borrower can be incredibly tenuous. The mentor’s madness is not a one off: it is a similar act of faith, that the only way we can escape this debtor’s prison from all the acts of kindness and help we could not repay is to put a brick in someone else’s wall that they, too, cannot claw out.

It’s not a selfless act, or at least it’s hard to commend something as selfless when there is no other choice. The person is, on some level, scrambling for a way to pay back something that cannot be paid back, and so hurls that gift forward, in hope that this is good enough: it may not find its way to the person who helped you, now lost forever, but perhaps someone like her. Ironically, the mentee is not your younger self; the mentee is the person on the other side who helped that younger self long ago. I do what I can to show gratitude where I can and to let people know the difference they made years later, but let’s be honest, it is not good enough. The only rational choice in the face of the debts we all bear from accepting the help required to get us to this moment is to help someone else, not for what we get out of it, but for what they take from us: an IOU, yellow and crumpled, written long ago.

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