Mentoring and dating share a lot in common. Are you not convinced? Read on.

In the first post of this series, I explained why having a companion on your life journey is necessary. In the second, we demystified the mentor, saw what they are and what they do. In the third, we discussed the mentors' motivations for giving their time to others. In the fourth, we explored the most central role, the mentee. In this fifth part, we want to discuss the birth of a mentoring relationship.

The dating analogy

After every talk I give about mentoring, someone comes to me and asks some form of the following question:

"I want Alex to be my mentor; how should I ask?"

Walking up to Alex and asking them to be your mentor would feel the same as walking up to strangers and asking their hand. Not something we usually do since it is utterly awkward. That is the reason why this question always comes up.

In this article, I want to suggest a different course of action. The mentoring relationship is a consequence of having built a professional association of mutual trust and respect. It is not a prerequisite for building that relationship.

My story

My first mentoring failure

I remember the first time I heard about mentoring. I then decided: "I'm going to walk up to Golo and ask him to be my mentor" (Golo, if you read this...๐Ÿ˜…). My knees were shaking. I stuttered when talking to him. I tried to say something funny. Or at least not too embarrassing to get to speak a second sentence. And I ended up not talking about mentoring at all. I decided mentoring was too awkward and not worth it and forgot about it for a year. This experience threw me back a few years, at the time of my teenage parties, where I couldn't muster the courage to introduce myself to anyone, let alone speak with the girl of my dreams.

This experience had the nasty effect of making me give up searching for a mentor. But thankfully, I continued searching for a mentee.

My first positive experience

I then experienced mentoring the other way around. I was lucky enough to meet my first mentee, almost by accident. He was a young developer, eager to learn and always searching for answers. The way this emerged was neither controlled by him nor by me. We met and talked. Again, and again. We were working in the same building, on the same project. Thus we had many reasons to meet. This informal relationship lasted for months before I became aware of what was happening.

Only then did I begin to push him in one or the other direction, pull some strings, challenge him, and act as a mentor. It took us years to make it official that we were in some mentoring relationship.

In other words, we got to spend time together for a few months. We enjoyed each other's company. We texted to continue the discussions we had started in the evenings. All the while, no-one spoke of mentorship.

Boy-scout Rule of talking to people

Have you ever heard of the Boy scout rule? Robert C. Martin introduced it in the software world in his book "Clean Code." He reused the sentence of Robert Stephenson Smyth Baden-Powell, the father of the Scout movement:

"Try and leave the world a little better than you found it." It became "Try and leave the code a little better than you found it" in the book.

I made this sentence mine in the following way:

"Try and leave the persons you talk to a little more curious than you found them." That means opening the discussion.

It means leaving your partners with unanswered questions. It means pushing back on their preconceived ideas and trigger their curiosity. It means opening discussions where your counterpart thinks you both have reached the end of this topic.

The ultimate guide

This process is how I start a mentoring relationship nowadays. I begin with building a relationship. I try to ignite the curiosity of my counterpart. If this curiosity-fire starts, I then try to feed it with questions. Then I "try and leave the persons I am talking to a little more curious than I found them." If that person comes back, with or without an answer, I've done my job right. If they do not, I try a few more times. If it still doesn't work. That wasn't supposed to be.

The next step

Now that the fire started, when should we put the word "mentoring" on it? My answer is always a question: "why would you want to do that?". I see one good reason, and it has to do with a push- vs. a pull-model. Let me explain.

After months of building this relationship with someone, it might become evident that we are in a "special relationship." We meet, we're having fun and enjoy our mutual company. We both feel like we're going somewhere, and we both feel we need those encounters for our personal growth. If this is the case, I don't see why one would need to make it official.

That said, it often happens that one of the two parties hasn't realized what is happening yet. They haven't, however, recognized the mentoring relationship for what it is. We might still be in this relationship-building phase, where one of the parties is actively trying to make the relationship grow. That's a push-model.

The pull model

There are two reasons for going away from this push model.

First, it makes a lot of sense from a development perspective. When you seek an answer, you remember much more information when you already know where you are going. If you are in the driver's seat, you are in control. That's why anyone who seeks a mentor should first introspect. Do you know where you want to go? Do you know what you want out of this relationship? The mentee should drive, not be pushed around indefinitely by a mentor.

When a mentee isn't that far yet, it makes sense for the mentor to help them find their answer by being in the driver's seat via a push-model. And when the time comes, a pull-model can emerge.

On the other hand, pushing one person is a challenging task. It is something you have to do repetitively and something that is almost always on your mind. You can only move so many persons at one time. Before we had our second child, I found that I could push two persons simultaneously. Since then, one has become the maximum. It is thus a self-preservation mechanism to switch from a push to a pull-model. This pull-model allows the mentor to spend their energy starting a new fire elsewhere.

Back to putting wood into the furnace

Until now, we assumed the mentor was triggering interest in the mentee. That was the "push." So, what is this "pull" I'm talking about? It's the assumption that from now on, the mentee will drive the relationship. The mentee will bring the initial topics for our meetings. The mentee will call out the sessions when they need them. The mentor is thus in a more reactive (yet not passive) state. The mentor waits for the pull to happen and then react to it by putting some wood back into the fire using the boy-scout rule of relationships.

The job of the mentor is thus to answer the call. The mentor strives to trigger more questions than they provide answers. It also means providing context and helping out of your experience. It means showing other possible directions and leading the way. It means asking why and opening the discussion. It finally means providing answers that are correct enough to solve the problem right now but showing the question that ensues.


Starting a mentoring relationship has a lot to do with dating. Both are relationship building with high-stakes. It is awkward. We sometimes wish someone could set us up with the person in question. And that's why the business of "mentorship-programs" exists. And this might become the next part of this mentoring series.

In the meantime, we learned that, like in dating, we shouldn't skip the first steps. We must talk. We must get to know each other. We must build mutual trust. We must show who we are and what we've got. We must be authentic. We must trigger interest in the other person, etc. Then, only then can we start talking about mentoring. Maybe.

This article was the fifth of my mentoring series. Here's the fourth part if you missed it. And here it goes to the sixth part, about mentoring programs.

Do you have questions? Please write your feedback in the comments below. I will tailor the upcoming posts to your needs!

Photo by Joshua Ness on Unsplash