If you haven’t had or been a mentor, it’s something that is worth thinking about. The right mentor can be inspiring, opening your eyes to new ideas and helping you tackle bigger and bolder challenges. It can also be a lot of fun for the mentor, who gets to coach enthusiastic people without having to deal with the day to day stresses of direct management (I think it’s a bit like being a grandparent – you get to do a lot of the fun parts, without all the responsibility). I’ve been lucky enough to have some really good experiences with mentoring, though I’ve also seen plenty that didn’t work out so well.
Picking the Right Mentor
Since this is a relationship between two people, obviously it matters a lot whether there is a good fit. What kind of person should you look for as a mentor? Some things to consider:
- The mentor probably should be further along in their career, but maybe not too much further. You want the mentor to have some wisdom and perspective you don’t have (yet). However, if they are vastly more senior, they may not be as useful in terms of helping you get your job done. A lot of really senior people have forgotten how to be effective at more practical jobs. They may have really interesting ideas and advice to share that are eye-opening and inspiring (or depressing!) to hear about, but often those insights have relatively little relevance to you day to day. So if you are shooting the moon in terms of connecting with somebody much farther along than you are, keep in mind that you may get less immediately useful advice.
- Look for somebody with different life experiences. When I first become responsible for a business, my background was in pure engineering. I was lucky enough to have a mentor who had successfully created a billion dollar business within Microsoft. He was full of insights that I desperately needed to understand, and I learned a tremendous amount from him during our discussions. I bombarded him with questions about working with the sellers, pitching to enterprise customers, helping to close deals, and doing the crucial back office arm wrestling with the sales team.
- It’s helpful if you have something in common. There are many benefits of diversity, but there is a lot of evidence from relationship research that people who have more in common tend to be more likely to form lasting relationships. I’ve found that it can be harder for mentors to really connect and add value if they come at the world with a radically different model than their mentee.
At the end of the day, probably the most critical thing about making a mentoring relationship work is “do you like each other and want to spend time together?” Mentoring is usually optional, and everyone is very busy, so it will take an effort to get and keep meetings on the calendar with a hundred other priorities competing for attention.
What Do You Talk About?
You might get a mentor who has a very well defined notion of what to do during your 1:1, and has a plan for it. You might also sprout wings and discover that you can fly (hey, it could happen!). For everyone else, you want to have a plan – most mentors feel like they’ve done their bit if they have actually cleared space on their calendar and are ready to meet with you.
I like to prep for a mentoring session by bringing in a set of topics to see which ones intrigue the mentor. I usually bring in three or four for an hour discussion, so we have good fodder even if one or two of them aren’t a success.
A couple of things that have worked well for me:
- Pose a problem I’m wrestling with. Obviously you will get more value if it is in a domain they know about. For example, if they are an experienced manager, they are likely to have been in a situation similar to one you are dealing with and have ideas about how to handle it. At least they can usually give you lots of cases where they tried things that didn’t work! Once, I was working with a direct who was really struggling, and I talked things through with my mentor. I knew in my heart that it probably wasn’t going to work out, but I didn’t want to admit it. After we talked, my mentor said something that really stuck with me: “Every time I have failed with somebody, I always waited too long. I’ve never moved too quickly.” That’s been true for me, too. I don’t like to give up on anyone, especially a talented person I like but who is in a role where they aren’t and won’t be successful. Getting a trusted outsider’s opinion can help you realize when you’ve dug yourself into a hole.
- Hunt for best practices. Yes, I will admit that I am a bit obsessed with best practices – that’s a lot of what I write about on this blog – because I love to find tools, ideas, approaches that are really effective. I’ve gathered a tremendous number of great ideas from other people, and I’m always on the hunt for more of them. I’ve found that most successful people have a “toolbox” that they apply in a wide variety of situations. Some people are very “meta” and will be able to quickly articulate those best practices. So you can ask “When you <do some activity>, what works really well for you?” (where the activity might be anything from managing a team to doing an all-hands presentation to preparing a board review to architecting a high-scale distributed system). Others are not so good at this, so you need to tease the best practices out by asking more specific questions: “Last fiscal year, how did you get your scorecard targets right, and what worked/didn’t work well?” “When you built the back end for that service, how did you minimize the time to recovery when the database instance failed? How would you change your design if you were starting over?”
As a mentor, I use some of the same conversations that I have with my directs as a manager (and which I’ll be writing up as separate posts), like “what do you want to be when you grow up?” and “how to ace your exit interview”. These are exercises that I think can really help people introspect and come to useful insights.
Have you had great or awful mentoring experiences? What worked and didn’t work?
Force Multiplier 
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