Mentoring Is a Multiplayer Skill

Mentoring is often treated like a favor.

Someone senior offers perspective. Someone junior receives guidance. The exchange is framed as generosity on one side and gratitude on the other.

That framing breaks mentoring before it even starts.

Real mentoring isn’t a favor. It’s a contract.

Not a formal one. A human one. An agreement that both people are responsible for what happens next. Without that shared obligation, mentoring quietly collapses into advice, reassurance, or well-meaning conversation that doesn’t compound into anything meaningful. 

That’s why so much mentoring feels sincere — and ineffective at the same time.

Apprenticeship Was a Contract, Not a Courtesy

For most of history, learning a trade wasn’t framed as generosity. It was an agreement. An apprentice didn’t “receive mentorship” from a master craftsperson. They entered a relationship with obligations on both sides. The apprentice committed time, effort, and discipline. The master committed attention, correction, and eventually, trust.

No one confused that arrangement for a favor.

What made apprenticeship work wasn’t hierarchy or proximity. It was consequence. Progress was visible. Feedback was constant. And both parties had something at stake if the relationship failed.

That structure didn’t just transfer skills. It transferred judgment—the kind that only forms when responsibility is shared.

What Changed When Learning Scaled

The Industrial Revolution changed how we learn. Apprenticeship gave way to classrooms, certifications, and standardized curricula. Knowledge became something you could receive without being accountable to the person who taught you.

That tradeoff made learning scalable. It also quietly dissolved the contract: you could learn about something without being responsible for what you did with it.

Mentoring survived as a concept—but not as a structure.

The “Pocket Peer” Escape Hatch

One of the quiet ways people avoid that contract is by staying inside what I think of as the pocket peer.

It has never been  easier to surround yourself with people who share your life stage, assumptions, and uncertainty. Group chats and text threads carry your old context forward effortlessly. That continuity feels supportive. But it also removes something essential: obligation.

Peers can offer empathy without expectation. Validation without consequence. Advice that doesn’t require follow-through. When nothing changes, no one is surprised.

That isn’t a flaw in peer relationships. It’s their nature.

But when peer advice replaces mentorship, learning quietly stalls. You hear reflections of your own thinking instead of pressure on it. You get reassurance instead of judgment. And because no one is invested in what happens next, nothing is at risk.

The pocket peer feels safer because it doesn’t ask for accountability

Which is precisely why it can’t replace mentorship.

Where the Loop Breaks

AI is the logical end of that progression.

It gives answers without expectation. It doesn’t care what you do next. It doesn’t remember whether its advice worked. It doesn’t adjust its thinking based on outcomes.

Mentoring works differently. Someone expects you to act. Someone expects to hear what happened. Someone revises their thinking based on your results.

For now, that loop still requires people. 

Context Doesn’t Transfer on Its Own

When I worked as a database administrator on Wall Street in the 1990s, my expertise lived in places you couldn’t document — heat in server rooms, pressure during outages, the intuition that something was about to fail before it did.

Years later, I watched that mechanical expertise disappear almost overnight as engineers spun up redundant databases in minutes in the cloud.

What didn’t disappear was how I thought under pressure. My value was never the commands I knew. It was the judgment behind them. And none of that lived in documentation. When I eventually left Freshworks, much of that connective knowledge left with me—because it had never been written down.

Mentorship is the only reliable way that kind of context survives.

Raising the Game

Mentoring isn’t a one-way transfer of wisdom. It’s a shared exposure to reality. Mentors often learn more from answering questions than the mentee learn  from the answers themselves. Not because anything is being withheld —but because real situations force sharper thinking on both sides.

When someone takes advice seriously, the work isn’t over when the conversation ends. Ideas collide with reality, and the outcome becomes part of the learning.

That pressure sharpens everyone involved.

The Unspoken Rules of Mentoring

Some of the most effective mentoring I’ve experienced came with rules—sometimes explicit, sometimes uncomfortable, always clarifying.

One of my earliest mentors, Mike Ross, was very clear about his.

His first rule was simple: If we agreed I was going to do something, I did it.

If I wasn't willing to do it, then it probably didn’t make sense for us to work together.

That may sound harsh. It isn’t. It’s pragmatic. 

If there is no expectation of follow-through, mentoring quietly degrades to conversation.

The second rule mattered just as much: Tell me how it worked out.

That wasn’t accountability for its own sake. That’s how we learned.

Most advice isn’t pre-baked. It’s synthesized in the moment—shaped by context, constraints, and real questions. When results come back,the loop closes.

That’s what turns mentoring into a learning system instead of a one-way exchange. This is why mentoring is a multiplayer skill. It only works when both people are actively playing.

Building Human APIs

My “cup of coffee” conversations at Freshworks were valuable. They just weren’t mentoring.

Those conversations had no agenda. No expectation of follow-through. No shared definition of success. They weren’t about guidance or direction. They were about connection.

They made the organization more navigable. They lowered the cost of reaching out. They helped context move sideways instead of always up and down the org chart. They made it easier to ask for help before something turned into a bigger problem.

That kind of casual interaction matters. A lot.

But it serves a different purpose.

Coffee chats create surface area. They make it easier for people to find each other, to compare notes, to ask for help when something breaks.

“Mentoring asks for commitment”

It asks for shared attention, or an agreement — explicit or implicit — about what “progress” would look like and how you’ll know whether you’re making it.

Casual conversations make organizations function better.

Mentoring helps people grow.

Both are important.They just shouldn’t be confused.

Berkson's Bits

"I'll shake your hand on the way in, and I'll shake your hand on the way out. And in the middle I hope we have fun and do some good work."

If you've ever been interviewed by me, you've heard me say that. If you stay in any job long enough, you'll see friends and colleagues come and go. It's part of the normal course of things. It's my expectation even at the interview stage. What I always hope is that people enjoy their time, learn, grow and do something worthwhile.

What I'm Listening To...

I’m more than a bit obsessed with bass players. If you do a search for the top bass players of all time it will include icons like Larry Graham, Jaco Pastorius, Bootsy Collins, Marcus Miller, Flea, and Victor Wooten. The one woman on the list is the iconic Carol Kaye. Listen to the intro to the Beach Boys Good Vibrations. That’s Carol.

This week I’ve been listening to some women who made their mark playing bass. Prince was one of the greatest musicians and performers of all time and from 2010-2016 his bass player was Ida Nielsen. Here she is with her band giving us some funk.

No one I know who’s made it did so without a mentor somewhere along the way. What’s striking is how little we talk about how to do mentoring well—on either side.

If you’re in a mentoring relationship right now—on either side—it’s worth pausing to ask a simple question: 

How do we know if it’s “working”?

Not as a goal or metric.

Just enough clarity to know whether you’re moving toward something together—or just talking past each other. That question has a way of focusing the value in the interaction.

Thank you to all my mentors who learned with me.

Looking forward to continuing the conversation…
Alan