Why I Wrote a Book About Mentoring (And Why It Took Me This Long)

I have been teaching managers how to lead since 1981. That is, by any reasonable calculation, long enough to have seen most management fashions arrive with considerable fanfare and depart with rather less. Competency frameworks, 360-degree feedback, servant leadership, agile this and holistic that. Some of it has been genuinely useful. Much of it has recycled the same core insight in different packaging and charged accordingly.

Mentoring has largely escaped this cycle of reinvention -- not because it is immune to fashion, but because it is old enough and robust enough to outlast it. The basic structure of a more experienced person helping a less experienced one to develop their judgment and navigate their career is, as far as anyone can tell, roughly as old as organized human endeavor. What changes is how well or how badly we do it.

After four decades of working with managers and leaders across more than 33 countries and 80 organizations, I have a reasonably clear answer to how well we do it. The honest answer is: not as well as we could. And the gap between what most organizations say about mentoring and what actually happens inside mentoring relationships is, in my experience, considerable.

That gap is why this book exists.

The problem is not that managers are unwilling to mentor. Most of the managers I have worked with are genuinely motivated to support the people around them. They recognize that developing talent is part of their job, and many of them find real satisfaction in doing it. The problem is that the transition from manager to mentor is harder than it looks, and almost no one receives any meaningful preparation for it.

Managing and mentoring are different activities. As a manager, your job is to direct work, evaluate performance, and deliver results through other people. The organizational hierarchy does a portion of the motivational work for you. As a mentor, none of that applies. Your only leverage is being genuinely useful. If your mentee leaves a session having gained nothing, they will not tell you that directly—they will simply find reasons not to schedule the next one.

What most managers do, without quite realizing it, is manage without the job title. They advise when to listen. They solve when they should be questioning. They know when to step back. The relationship stalls, the mentee disengages, and the mentor concludes -- incorrectly but understandably -- that mentoring is simply not worth the time.

I have watched this pattern play out in organizations of every size and in every sector. I have also watched it play out in my own mentoring, particularly in the early years. My first mentoring conversation went about as smoothly as you might expect when one party has no idea what they are doing, and the other is too polite to say so. The experience was instructive, though not in the way I had planned.

What I came to understand, gradually and sometimes painfully, is that effective mentoring is less about accumulated expertise and more about the quality of attention you bring to a specific conversation with a specific person at a specific moment. The mentors who do this well are not following a framework. They are improvising -- in the best possible sense of the word. They have prepared thoroughly, and then they set the script aside and respond to what is actually in front of them.

That insight is the central argument of From Manager to Mentor: Conversations You Cannot Rehearse. No two mentees are alike. No two conversations follow the same path. The mentee who arrived last month with a clear career goal may arrive this month in the aftermath of a difficult performance review, a restructure, or a realization that the goal itself was wrong. The mentor who is committed to the plan they drew up in session one will miss what matters most in session five.

The book addresses eighteen distinct mentoring challenges, from building trust and contracting expectations to navigating ethical dilemmas, managing conflict, and knowing when a mentoring relationship has run its course. Each chapter is written to work as a standalone resource, because real mentoring challenges do not arrive in a tidy sequence. They arrive when they arrive, and the effective mentor needs to locate relevant guidance quickly and apply it immediately.

I have also tried to be honest about the costs. Mentoring requires a particular kind of attention that is different from chairing a meeting or reviewing a quarterly report, and for action-oriented managers accustomed to solving problems and moving on, sitting with ambiguity can be genuinely uncomfortable. Some mentees will take your most carefully considered insight and completely ignore it. Others will attribute the same idea to someone else six months later. If you need visible, attributable results to sustain your motivation, mentoring will test you.

But the return on that investment, for both the mentor and the mentee, is considerable. The research is detailed on this: mentors develop their own leadership skills, expand their professional networks, gain access to perspectives they would not otherwise encounter, and report higher levels of job satisfaction than their non-mentoring counterparts. And for those at a career stage where the question shifts from "what can I achieve?" to "what can I pass on?", mentoring is one of the few professional activities that genuinely allows you to shape the next generation of leaders.

That, in the end, is why it took me this long to write the book. It is not the book I could have written in 1990. It needed the full four decades -- the failures as much as the successes -- to get it right. I hope it saves a few readers some of the time I spent learning the hard way.

From Manager to Mentor: Conversations You Cannot Rehearse is available on Amazon.