“Will you be my mentor?”

It’s time to reconsider formal mentoring relationships and the need to have an official “mentor”. You simply can’t force mentoring relationships. The best relationships are those that grow organically over time and develop into a deep mutual respect.

When I first read Sheryl Sandberg’s book “Lean In”, the chapter on mentorship made me uncomfortable. Entitled “Are you my mentor?”, Sandberg argues that people who want to be mentored should never approach another person and ask them to mentor them outright.

I was pretty sure I had asked at least one person to do this in the past, and had certainly had people approach me with this question, so my first reaction was defensiveness: “Why is that question so wrong?”, I thought.

Upon much more reflection, I’ve figured it out: you can’t force a mentoring relationship. Unfortunately, many start out in this way, and therefore I encourage you to start off slow and grow your mentorship relationships organically.

The reason? Mentorship relationships involve humans, and humans are messy. To have a successful mentoring relationship, there has to be a strong bond between the two participants. They have to find each other intellectually stimulating, have compatible temperaments, and be genuinely interested in each other’s wellbeing.

I have had this fail in both directions. I have asked people to ‘be my mentor’ and later realized that we just weren’t compatible — it felt like their advice was coming from their place of truth, but wouldn’t translate to me. Likewise, I’ve had people ask for me to mentor them that I didn’t really gel with or see much potential in. Unfortunately, it’s incredibly hard to invest in a ‘mentee’ when you aren’t genuinely interested in their career development.

My point is this: if you’ve only seen someone speak at a conference, or met them briefly at an event, or have only seen what they produce online, you can’t possibly predict whether a bond will form between you. So why would you commit to having a certain type of relationship before you know if you’re compatible?

This isn’t to say that you shouldn’t reach out to people you find exciting and interesting. Not in the least! What I’m saying is that you shouldn’t try to formalize something too early (or perhaps, ever) before you actually know if you two are a good match.

My recommendation is this: consider starting — and keeping — things casual, until they potentially evolve into something more. If you’re interested in learning from someone, great! Approach them and ask them:

Would you be willing to go for coffee with me (or meet online) to discuss X topic?

It’s as easy as that. It’s best to give a specific topic so that the potential mentor can decide whether they have something of value to share.

Once you meet and start getting to know each other, that’s when you can start deciding whether this is someone whose opinion you’d like to call on again. But stop — this doesn’t mean you ask them to be your mentor at the end of the meeting! This is just where you gauge your mentor’s reaction. Ask them if they might be willing to do this again sometime. If the answer is yes, fantastic. This means that you should just file away a note in your brain that says, “Hrm, that was really helpful advice. Perhaps I will call on ________ to help me out next time I need assistance.”

Really, there is no need to formalize at this point. In fact, I would argue that there might never be a need to formalize. As long as you’re clear about whether the person you’re asking advice of isn’t feeling imposed upon, and is willing to continue giving their time, that’s all that matters.

The fact is that if you start calling on this person for advice periodically as you move through your career, and over time you develop a professional closeness and investment in one another: that person is your de facto mentor anyway. The more close you become, the more time the person will be willing to invest. There’s no need to ever even call them a mentor, necessarily. Doing so might put unnecessary pressure on a fragile human relationship.

Simply reach out to people you think you can learn from, whether they are ‘peers’ or people more senior to you, and see where the relationships evolve. I think you’ll be happy with the results!

(An aside: the key here is actually reaching out. Speaking as someone who has struggled with self-confidence and shyness in the past, I know how difficult this can be. But the more I’ve moved in user experience circles, the more I’ve realized what fantastic and giving people work in this field. Everyone is always on the look-out for new people entering the field who are motivated and bright. Costa Rica . Know that if you reach out, you will almost always be welcomed with open arms. Try it!)

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