Help! My mentee isn’t listening to me!

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@ nickcald Nick Caldwell CPO @ Looker | ex Reddit, Microsoft| 👨🏾‍💻=💰🔗

Quick article while I wait for Game 2 of Warriors Cavs. Last week I had a fantastic conversation with a top employee on my team. He’s an up and coming Senior Engineer who recently started mentoring newer recruits. He asked me:

“As a mentor, should I be a sounding board or should I take on a more active role and give advice? I’m uncomfortable telling people what to do.”

This is a great question because there are many approaches to mentoring and leadership styles. Sometimes it makes sense to apply what is referred to as a “coaching” style, where you ask leading questions in an effort to try and get the mentee to figure out answers on their own.

More typically, mentees have some expectation that they will learn from a mentor’s past experiences and get tangible advice. If they wanted a sounding board they could hit up the water cooler, get a counselor, talk to mom, etc. Instead they’ve chosen to spend time with you. Mentoring ain’t therapy.

“But when I do give advice, my mentee rarely follows my instructions. What am I supposed to do?”

Ah! Perhaps the most common mistake that new mentors make is assuming that mentees will, or even should, act on their advice. Why? Follow me through two claims.

Claim 1. Mentoring is not actually a 1:1 relationship

Of course your mentee will come to you for advice but, let’s be honest, when is the last time you had a problem and talked to only one person about it? Just yesterday I had a 3 minute conversation about compensation philosophy with the guy making me ice cream at Humphry Slocombe. Trust that your mentee is going to talk with a whole bunch of people about their problems: spouses, friends, coworkers, their hairdresser, the guy who makes them coffee, Blind trolls, whatever. A smart mentee is building a portfolio of advisers and you are but one highly-valued page in that portfolio.

And what about you? When you answer a mentee’s questions are you purely drawing on your own thoughts or are you synthesizing the collective wisdom of all the people who mentored and coached you before? Does any of this sound like a 1:1 relationship?

Not an Esher painting, real people have to commute on this freeway.

Mentoring isn’t a 2-way street, it’s the LA freeway system: no one understands how it’s all connected, everyone’s got a different destination, and the journey is going to take way longer than anyone wants.

Mentees DO want your specialized knowledge, but they are still going to map their own course.

Claim 2. You aren’t as right as you think you are

I consider myself a reasonably smart and moderately successful person, yet I will only take credit for being right about 60% of the time. And over the years I’ve gotten to meet and work with many great leaders, people much smarter than me, and I suspect that even the very very very smartest of them are only right about 75% of the time. Take a second to think about that, and while you do here is some evidence:

My personal childhood hero, Bill Gates, produced a real collage of questionable decisions including Bob, Clippy, entirely missing the internet, and ignoring government regulators.

His biggest rival, Steve Jobs, fired off a few duds as well. Anyone remember NeXT computers or the G4 Cube? Interestingly, Jobs also managed to recruit the guy who got him fired from Apple.

Even today’s heros aren’t immune, did you know at one point Elon Musk was fired for wanting to switch PayPal's infrastructure from Unix to Windows? Imagine a Windows-powered fleet of self-driving Teslas for a moment. Clippy take the wheel!

My point with all this is: what’s your percentage? As a mentor you’ve got to accept that while you may have an outsider’s perspective of how to address a problem, your mentee is actually living in it. Your job is to provide additional datapoints that will help them navigate the issue as best as possible. But expecting a mentor to directly follow your advice would be like trying to drive a car while locked in the trunk.

Recognize and honor the uniqueness of your mentee’s situation. They are in the driver’s seat. Set your own expectations accordingly.

“OK, so what’s the point of mentoring if I’m not a sounding board and my mentee doesn’t have to listen to me?”

There are three ways to answer this.

First, it’s not about you. Leaders make new leaders.

Second, (and yes, I know this is trite) mentoring and mentoring programs are simply great additions to any company. Companies with mentoring programs develop new leaders faster, retain more talent, are more diverse, and have higher workplace health scores. Here’s a good article about all that.

Finally, I’ll make a controversial claim and say that mentoring relationships are just as valuable for the mentor as the mentee. Mentoring forces you to be able to self-reflect on your own experiences, squeeze out the learnings, and articulate them to someone else in a coherent and relatable fashion. By doing this you not only help the other person, but you better understand yourself.

That’s all for now, thanks for reading

Waaaariors!

-nick

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