A prominent Philadelphia retailer once told me the surest way to be mentored by her was never to ask. The people she ended up investing in were the ones who simply kept showing up (volunteering, staying curious, doing the work) until one day she looked up and thought, I want to help this person grow.
That insight has stayed with me. It reframes mentoring entirely: from a transaction you initiate to a relationship that is earned, from the perspective of the mentor and the mentee.
I recently spoke with Lisa Fain, CEO of the Center for Mentoring Excellence and coauthor of Bridging Differences for Better Mentoring, about what organizations and individuals consistently get right—and wrong—about one of the most powerful human development tools we have.
Avoid sage-on-stage
The most common misconception Fain encounters is that mentoring is about knowledge transfer—the experienced elder dispensing wisdom to the eager apprentice. That model is not only outdated; it’s actually counterproductive.
“The first thing a lot of people get wrong,” Fain told me, “is that they don’t understand that mentoring is, at its heart, a reciprocal relationship.” Real mentoring generates learning in both directions, through what she describes as an interpretive lens: Here is how it was for me. How might it be different for you?
That curiosity about lived experience, about the rationale and mistakes behind decisions, is something AI can approximate but never replicate. It requires sentient intelligence: the distinctly human capacity for contextual awareness, empathy, and relational knowing.
Change happens in the dissonance
The second mistake is defaulting to sameness. Leaders gravitate toward mentoring people who remind them of themselves, or they avoid discussing differences altogether, as though difference divides rather than develops.
Fain is direct about the cost: “The message you’re sending is, ‘I like you in the ways that you’re like me, so be more like me.’” Homogeneity shortchanges growth.
My West Coast Swing dance teacher put it another way recently: Change happens in the dissonance. Not in congruence, not in sameness, but in friction. A mentoring relationship engineered for comfort will produce more of the same. One built across difference, with the courage to ask “What am I missing?” will transform both parties.
Programs create culture—but culture is the point
Fain rarely has to sell the business case for mentoring anymore. What organizations still miss is that a mentoring program is a seed, not the harvest. The real prize is a mentoring culture—one that builds the human skill of developing oneself and developing others, inside and outside any formal structure.
“Pair and pray,” as Fain wryly calls the launch-a-cohort-and-hope approach, is not a strategy. A program creates the conditions; the culture does the work.
Which brings us back to that Philadelphia entrepreneur’s insight. If you want a mentor, don’t lead with the ask. Start with the what: What do you want to learn?
Find someone who embodies it. Tell them specifically what you admire. Request one conversation. Follow up with what you did with it.
Earn the relationship before you name it. That is not only a good mentoring strategy. It is, as Fain describes it, the beginning of transformational learning.