Mentoring and dating share a lot in common. Not convinced? Read on. And by the time you finish this article I promise you will never see your mentor the same way again...

The movie The invention of lying, from and with Ricky Gervais, describes a world without lies. In this world, everything we say is the truth. Now, what would happen if one person in this world discovered lying?

The second scene of the movie is a dating scene. Here is the script. And remember, lying has not been discovered yet.

Mark (40's), average to semi-handsome, twists and turns through stucco hallways. He knocks on apartment "9C". Jennifer opens, her face flushed. She's beautiful.

Jennifer: "Hi. You're early. I was just masturbating."

Mark: "That makes me think of your vagina. I'm Mark, how are you?"

Jennifer: "A little frustrated at the moment. Also equally depressed and pessimistic about our date tonight. I'm Jennifer."

Mark: "I hope this date ends in sex."

Jennifer: "Not me. I don't find you attractive. Come on in."

Mark enters.

In the first post of this series I explained why having a companion on your life journey is necessary. And in the second post of this series we demystified the mentor, saw what they are and what they do. In the third post of this series, we discussed the motivations of the mentors for giving their time to others. In the fourth part of this series, 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

Imagine walking to the partner of your dreams and suggesting not a drink, not a date, but for sex or even marriage right away. Like Mark in this movie. Crazy, right?

After every talk I give, someone comes to me and asks some form of the following question: "I want Maria to be my mentor, how should I ask?". Well, going up to Maria and asking her to be your mentor would feel like being Mark. Don't be like Mark.

In this article, I want to suggest a different course of action.

Since our first teenage parties, we have learned to embrace our fears. We have learned to walk up to those persons that make our knee feel like Jell-o. We have learned to master our stuttering. We have learned to tell something funny... or at least not too embarrassing to get to say a second sentence. Or not. And when we failed (I know I did), we didn't give up. Why should we expect something else when dealing with a mentor?

Way to go Tim

I remember the first time I heard about mentoring. I then decided: "I'm going to walk up to Maria and ask her to be my mentor". My knees were shaking. I stuttered when talking to her. I tried to say something funny... or at least not too embarrassing to get to say 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. Way to go Tim, way to go.

To be honest, I didn't give up. I gave up searching for a mentor. In the meantime, I continued searching for a mentee.

The lucky move

I then experienced mentoring the other way around. I was lucky enough to meet my first mentee, almost by accident. A young developer, eager to learn and always searching for answers. The way this emerged was neither controlled by me nor by him. We met and talked. Again, and again. It's only after a few months that I began to push him in one or the other direction and pull some strings. And it took us years to make it official that we were in some kind of mentoring relationship.

In other words, we got to spend time together for a few months before coming to the first date. And then there were a lot more dates before we made it official that we were together. It took us even more time to become physical. Wait, am I still talking about mentoring? smiley-face

Boy scout Rule

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 in his own terms 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 as much as you can. This works wonders with mentees.

The ultimate guide

And that ladies and gentlemen, is also the way I start a mentoring relationship nowadays. I try to start a fire. I try to ignite their curiosity. If this curiosity-fire starts, I try to feed it with questions. The fire can be small. If it starts, those questions are the key.

If a person comes back, with or without an answer, you've done your job right. If they do not, try a few more times. If it still doesn't work. Give it a break. That's it.

From "Single" to "In a relationship"

Now that the fire started, when do should we put the word "mentoring" on it? To which I'd like to answer: when did you change your Facebook status from "single" to "in a relationship"? When I want to go from a push- to a pull-model. Let me explain.

After a while, it might become obvious that we are in some kind of "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. Back in the dating world, we would automagically take this next step and make it official. Or decide not to. But we would both know that this is the next logical step.

In a mentoring relationship, one of us usually doesn't know it. Because they didn't recognize the relationship for what it is yet.

The mentor might even still be "force feeding" their mentee with questions. Feeding like in "feeding the fire" part above. 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, when you know where you are going, you remember much more information. If you are on the driver's seat, you are in control. That's why anyone who seeks mentoring "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 by a bossy-mentor.

But sometimes people are not that far yet. And it makes sense to help them find their answer by being in the driver's seat, via a push model. And when the time comes, pull-model can emerge.

Then, pushing one person is a hard task. You can only push so many persons at one time. My days only have 24 hours... like yours.

I personally found that I could push two persons at the same time. It is thus a self-preservation mechanism to switch from a push to a pull. This allows the mentor to "move on" to the next mentee.

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 every one of our meetings. The mentee will call out the meetings when they need it. 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.

The job of the mentor is thus to answer the call. The mentor must try to trigger more questions than provide answers. It also means providing context and helping out of 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.

And that's how you create a mentoring relationship. Like in real life, you talk before you date, and you date before you speak of marriage and plan kids.


Starting a mentoring relationship has a lot to do with dating. It is awkward. It doesn't feel natural. And we would totally prefer if someone could set us up with the partner in question. That's in fact what we are going to talk about in the next part: the match making business.

In the meantime, we learned that like in dating, we shouldn't skip the first steps. Talk. Get to know each other. Build trust. Show what we've got. Be authentic. Trigger interest in the other person. And then, only then, we can start talking about mentoring.

This is the fifth post of a series of articles about mentoring in which I explain you how to get started with it. Here's the fourth part if you missed it.

Do you have questions? Write your feedback in the comments below so that I can tailor the upcoming posts to your needs!

Photo by Joshua Ness on Unsplash