On Mentoring

My thoughts on the value you get from mentoring and being mentored, and how to make the most of it.

I’ve worked at Microsoft for almost 22 years. During all that time, I’ve never exactly had a mentor. I’ve had a few people I’ve asked to meet with me about specific skills or goals I was working on, a limited number of times. I’ve been a mentee in some mentoring rings. But I have mentored at least (checks notes) 21 people so far. I have 6 people I’m mentoring right now, and 3 more peers/friends I meet 1:1 on an informal regular basis. I feel like I’ve gotten quite a bit of value from it… Let’s talk about why and how.

The Why of Being a Mentee

It’s a little funny for me to lecture on the value of being a mentee, after I say I haven’t exactly been one myself. But I think I know, now, the main reasons behind that. Early in my career, mentoring wasn’t very common, so it never really occurred to me to ponder the question of getting a mentor until I was already 6 or more years in and at senior-level. At that point I asked myself the same questions I’ve heard from numerous new hires: What do I need a mentor for? What would I talk with them about, or ask them to do? Would I be using their time well? My answer was also the same thing most people hit: I dunno, and I guess I shouldn’t try unless I feel a reason to. Looking back, I actually think that was the wrong answer.

Here’s the core of what you should think about:

  1. You should have goals for yourself, and revisit them on a regular basis.
  2. Talking over your experiences and progress with someone helps you understand them more fully and learn from them.

In theory, you can get all of this from your manager. Some managers are good at these. But there are two problems that often get in the way. First, the two of you also have work to discuss, and it’s very easy to get lost in that. Second, you have a power imbalance between you, and that hinders frank conversations.

You can also get these things from talking to friends or peers. Some people cultivate a set of friends who will always be there with love and support – truly, I do this myself.

And of course, you can build a habit of reviewing and thinking about your goals on a regular basis on your own. I’m sure some people do this.

Whatever works for you is great! Everyone is different and I would never prescribe a solution. But if you’re finding that you’re not keeping an eye on your personal goals or getting chances to learn from others, you’ll find a mentor to be a great person to build these habits with. As far as will you be using their time well – gosh – if the meetings are a waste you’ll both know it! Don’t be shy, and read the next section to understand why your mentor is gaining from the experience, too.

The Why of Being a Mentor

Most people probably sign up to mentor due to wanting to help others. Caring to help others, and paying it forward out of gratitude for the fortune they’ve had in their own careers. But my years of mentoring have taught me there’s more than that. Mentors gain from the relationship, too.

Think about this:

  1. As you discuss your mentee’s experiences, you learn things from them, too! You think of what you’d do in the same situations. You’ll be more ready if those situations happen to you.
  2. As you discuss your own experiences with your mentee, you’ll hear their interpretation as well. Maybe they’ll think of some new angle you never saw, or point out some contributing factor you never noticed before. Or, you might realize these things yourself as you talk.

In other words, you accelerate how fast you gain experience! Imagine for a moment that you have 4 mentees; you might not be going through the experience of 4x as many situations as you would on your own, but you’d certainly be seeing quite a few more! Especially when I was a manager, I learned a lot about how to be a better manager by listening to things my non-manager mentees were going through: the ways their managers were helping them – or not.

So, going back to the reasons I haven’t had a mentor over the years. Over the years I’ve been mentoring, a lot of what I could get from a mentor, I get from talking with my mentees. I’m very open with them about my own career goals and challenges. I talk them through my thinking during times when I’m in the process of changing jobs. And all of that doesn’t just help them, it also helps me. My mentees are my support group, too.

Various notes on how

Ground rules

This really shouldn’t need to be said, but unless you hear something illegal or dangerous from a mentor/mentee, your conversation must stay private between the two of you. If you think someone else needs to know something, you should make that argument to your mentor/mentee, and respect their wishes if they disagree.

And never pressure someone to go into details/subjects they’re uncomfortable talking about. If you think it’s important, then suggest questions they should ask and answer for themselves instead of asking to hear the answers.

What do you talk about?

The first rule is, of course, that the mentee gets to set the agenda. If a mentee comes with a specific set of topics, they should have the ability to steer the conversation wherever they want it to go.

But you don’t have to be so structured or formal. If the mentee doesn’t have a specific agenda, the default agenda is:

  1. What goals is the mentee working on, and how are they going?
  2. Are there any recent questions, challenges or experiences the mentee wants to talk over?
  3. What goals is the mentor working on, and how are they going?
  4. Are there any recent questions, challenges or experiences the mentor wants to talk over?

If you feel comfortable being open between you, these are not difficult topics. Actually, if you’re not entirely comfortable being so open, it is good practice, too. Both for the mentee and for the mentor. And these topics open you up to many valuable tangents as the mentee gets curious along the way.

Asking for a mentor

It sounds like over-simplifying, but: pick someone and ask them to be your mentor! This can be scary at times. But people are going to feel honored that you asked, and glad to help, as long as they have the time and energy to do so. If you’re really worried, here are some tips that will make it easier to ask, and easier for your mentor to say yes:

  1. Set a time period. Instead of asking for an indefinite relationship, choose an ending point. 6 months? 1 year?
  2. Define goals. Are you working on something specific, that your requested mentor is great at? How can they say no to that?
  3. Choose your prospective mentor thoughtfully. Ideally they will be someone you feel comfortable talking to, and who is not too far removed from you in seniority. Don’t choose that partner level superstar unless you’re close to them in rank. Look for someone who is only 1 or 2 steps above you.

Again, you don’t have to do these things. It’s okay to ask for an indefinite relationship with unclear goals. Or to talk to someone several steps above you. But if you’re feeling nervous or unsure, these can make good guard rails. At worst, they’ll say no!

Remember how I have 6 mentees right now? My preferred number is 4. Guess how one person got me to exceed my preferred number? By setting a time period and having some goals.

[EDIT]: Another benefit of setting a time period is that it encourages you to talk to a variety of people. Each mentor will have a different perspective to share, and a different set of things they’re working through. I know it’s not always comfortable to build and rebuild close relationships with multiple people, but you’ll do yourself good by finding a new mentor every year or two.

Making use of hierarchy

It’s good sense that mentoring structure should mirror our hierarchy: the most senior people around shouldn’t be mentoring everyone. In Microsoft terms, Principal-level people should mostly mentor senior-level people; senior-level people should mostly mentor level-2’s; and level-2’s should mostly mentor new hires.

I see you, level-2 person who thinks you don’t have value to add as a mentor yet. I know, you’ve only been working a few years, but I challenge you to try. Not only will you see that you’ve learned more than you realize – you’ll also gain from mentoring as I describe above.

My own personal policy is never to turn away mentoring requests empty-handed: if you ask me to be your mentor and I decline, I’ll still meet once to get to know each other, and then help you find a mentor who I think will be a good match for you. Going back to that philosophy of hierarchy – it might be one of my own mentees.


If you’re meeting for a specific time period or purpose, the schedule might follow naturally. If your mentoring relationship is more open-ended, you’ll need to choose a meeting frequency that works well for both of you. I personally like meeting monthly for lunch – or I did, back before COVID when meeting for lunch was a thing. So as a mentor, my preferred schedule is a 4-week rotation where I meet 1 mentee per week for lunch. I had Wednesday lunches reserved for mentoring.


When you start mentoring, you should do a little exploration of what coaching is and how to do it. In a nutshell, it means listening and then asking questions which help your mentee find their own answers, instead of always giving your answers. Mentoring doesn’t always mean answering your mentee’s questions. Very often it means helping your mentee find their own answers.

Twice I have had mentees surprise me when they were struggling with making career changes: they knew they wanted to leave their current jobs, but weren’t sure what they wanted next. I suggested they spend some time thinking through their values and what life-goals were most important to them. One realized she wanted to work toward starting a non-profit, and decided to go to business school. Another realized she wanted to be a teacher. I never would have come up with those options for them!


When you are working on your career, you should also think about whether you need a sponsor: someone in a position of influence, who should know you well enough to understand your capabilities and goals, who could be watching for opportunities that would be good for you and putting your name forward. If you’re unfamiliar with sponsoring, you should learn more about it.

A Note About Diversity

Thank you for caring about diversity enough to put some thought into whether your diverse new hire should have a mentor. That’s good! Now, don’t go turning that into a mistake:

  1. Don’t look to underrepresented minorities to do all the mentoring. Role models are great, but if you have 1 senior engineer who happens to come from a minority group, they can’t single-handedly carry the whole set of junior engineers you’re trying to support. Use hierarchy, and use the allies in your organization: the well-meaning folks who want to help. That minority engineer is still a role model without being a 1-on-1 mentor.
  2. And for heaven’s sake, never force someone to be a mentor! Always ask politely, give them the chance to say no, and accept gracefully if they do. This might seem obvious, but I’ve heard recent examples from acquaintances who were “voluntold.”

I am 100% serious when I say: a female software engineer does not make it to senior or principal level without being asked to be a mentor. Multiple times. I’m sure Black and Hispanic/Latino engineers have similar experiences. They absolutely have to say no sometimes, and to make use of hierarchy to support a whole group.

P.S. don’t forget your less (visibly) diverse new hire either.

Alternative structures

Not all career conversation needs to be one-on-one. I’ve participated in “mentoring rings” multiple times: groups of people who are put together with one or more leaders to discuss career-related subjects. Instead of one-on-one conversations, these are 1-2 on multiple. The pressure to talk or to bring subjects is lower. But you get as much value out of these as you put in: someone must set an agenda, and if you don’t put much effort into that, you’ll get a bunch of low-value or awkward conversations. I generally come away feeling a bit lukewarm about mentoring-ring conversations; their value varies.

In Summary

I really enjoy mentoring, and gain a lot from it. I also gain a lot from the friends I meet on an ongoing basis and tend to discuss career stuff with. Everyone has different levels of energy for these kinds of things, and it’s OK if you don’t find yourself wanting a mentor or wanting any mentees. Since there’s a lot of potential value to be had, and you should at least try some things before deciding you don’t like them. But more than anything, you need to keep yourself in a rhythm of reviewing your personal goals, and how they’re going. For me, that means discussing them with my mentees and friends. Good luck finding your own balance!

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