How to approach mentoring from a generosity mindset
Mentee Spotlight: Robert Reeves
If you just graduated, odds are you’re not totally sure what career you want to go into.
To find an answer to this question, Robert turned to mentors. A lot of them.
Living in a new city, Robert Reeves found out what he wanted to do — and what he didn’t want to do — by connecting with a host of mentors. He reached out to existing contacts, to mutual acquaintances, and to complete strangers — and most of the time, he got a positive response. He met with several people, toured their offices, learned about their jobs, realized which careers he didn’t want to pursue, found one he did, and, ultimately, was recommended by one of his mentors for the job he now has.
How did he do it, you ask?
It was an impressive feat of networking, driven by a genuine interest in learning about the day-to-day life of people in a wide variety of careers.
“I look for people who share my interests, but I think also you can use these sort of connections to expand your circle outside of what you usually would experience. I’m willing to reach out to people who have knowledge and information that’s interesting to me, even if it’s maybe not my field.”
Of course, most of us already know mentorship is important. But that leaves unanswered a host of questions:
- How do you decide who to ask to mentor you?
- Should you go for a long-term mentor or for a one-time, flash meeting?
- Most importantly, how can you ensure that you (and — importantly — your mentor!) get real value out of your relationship?
Robert shared with us his strategies for initiating and structuring mentorships, including recommendations to make a small ask, to take a notebook to your meeting, not a phone, and not to make your mentor do the legwork of scheduling the meeting. But throughout, Robert continually emphasized that a spirit of generosity and respect was key to being a successful mentee.
“I think it’s that generosity, the giving mindset, that’s important. But it’s sort of a paradox that you also have to be totally open to receiving as well. So whenever it’s worked for me, I’ve gone in and said, ‘What can I do for you?’
“But I’m also not embarrassed about accepting help. That’s the absolutely crux of the mentor mentee relationship, it’s just this free flow of ‘Let me help you, I’ll help you,’ in a way that is mutually beneficial.
“So if you come in either just expecting to get stuff for nothing, or if you come in thinking ‘I’m not worthy, I’m here to worship at the altar of this more experienced person.’ Neither of those approaches works. You need to be giving and receiving with equal zeal.”
How it started…
Robert has been actively involved in mentorship for years, both as a mentor and as a mentee, but as creators of the student-alumni mentorship software PeopleGrove, we wanted to hear specifically about his experiences as a mentee on Harvard-Westlake Works, a mentorship platform set up by Robert’s high school alma mater, Harvard-Westlake School, and powered by PeopleGrove.
Robert got involved in HW Works after graduating from college.
“I was at a point in my life where I didn’t know exactly — or even at all, really — what I wanted to do, so the idea that I could have access to a bunch of really interesting people who had been down those roads I was interested in and whom I could learn something from — that was really attractive to me.”
He created a profile to “see what happened.”
But Robert’s engagement with the platform was far from passive. He thoughtfully selected interesting potential mentors, wrote carefully constructed messages to them, prepared extensively for his meetings with them, and always went out of his way to give back to his mentors.
Making the ask
When browsing profiles on HW Works for potential mentees, Robert primarily looked for people who shared his career interests. But he pointed out that you don’t need to limit yourself to career-related topics when reaching out to mentors.
“I’m willing to reach out to people who have knowledge and information that’s interesting to me, even if it’s not maybe my field.
“I reached out to a real estate professional, for example. I have no real estate experience and don’t intend to go into it, but I was interested. He met with me at a coffee shop, we talked for more than an hour, really casually, and I got all this fascinating information, and he was a super cool, interesting guy.
“I think you can use these sort of connections to expand your circle outside of what you usually would experience.”
Once he found someone he wanted to connect with, Robert would use the HW Works platform to send them a message.
He acknowledged that reaching out to potential mentors was “little nerve wracking,” but argued that the HW Works platform “helps mitigate that a little, because the people who are on there have kind of self-selected, they’ve basically already said ‘Hey, I’m open to talking to you.’”
Robert also attributes some of his networking best practices to the book “Never Eat Alone,” saying its suggestion of “doing a small ask” helped a lot. Strategies that have worked for him include asking for 15 minutes on the phone or for a quick chat over a cup of coffee, or even offering to bring a cup of coffee to the potential mentor’s office.
“I got really good responses. And the more good responses you get, the less intimidating sending that initial message is.”
Most importantly, though, Robert emphasized that you need to treat the potential mentor with respect, not as a resource to be exploited.
He tries to approach mentors “from a generosity mindset.” Pointing out that most mentors get requests centered around what they can do for the mentee, Robert reported that he’d made a lot of meaningful connections simply by “finding out what matters to them.”
He recommended that mentees “do a little extra homework on what you have in common with them — for instance, do they have a charity that you could come donate your time to? Don’t feel like you don’t have a lot offer the mentor. Just use your imagination, offer them something, and then be willing to ask for stuff (because they do want to help).”
Asked for some advice for first-time mentees, Robert recommended that they “just go for it.”
“I think young people don’t necessarily realize how eager people who are further along are to share what they’ve learned. A lot of them really delight in it, and a lot of them are not asked for their insight and mentorship as often as you would expect.”
What comes next?
“Just be open to wherever it goes. I’ve had a mentorship either be a one-time meeting or phone call that I got really fascinating information out of, all the way up to somebody who I started meeting with regularly and who got me a job! Mentoring can take all different forms, so just see how it works out.”
Sending that first message, making the ask — that’s just the beginning. From there, mentorships can go on to be meaningful connections that benefit both mentor and mentee, or stilted connections that leave both dissatisfied.
So how do you turn that initial contact into a successful mentorship? What makes a mentorship successful and fulfilling to both mentor and mentee? For Robert, there’s no cookie-cutter perfect mentorship.
“Mentorships all serve different purposes. My most objectively successful mentorship was with Brad; he was a little intimidating for me to contact, but he was on the platform, so I reached out to him. He met up with me and from the moment we started talking — we talked for over two hours — he was just asking ‘What can I do for you?’
“We really hit it off, we stayed in touch, and he ended up distributing my resume around to various companies that I was interested in, and I was hired at one in about a week. It can’t go a lot better than that.”
Even after landing his job, though, Robert continued to use HW Works to explore his interests and make interesting connections.
Robert pointed to two other mentorships he initiated through HW Works as examples of successful mentorships, even though he didn’t end up with a job coming out of either.
“What was different about these mentorships was that they were with people a little bit closer to my age, who were in areas I was considering working my way towards, and in both those cases I had incredible conversations that lasted multiple hours, made friends with people who were further along in their careers, and also realized that I actually didn’t want to go in the direction that they had gone with their careers.
“I think that’s something people don’t realize you can get out of these experiences: learning the things you don’t necessarily want to do.”
Robert’s mentorship with Brad continues — they’ve stayed in touch and continue to meet periodically. Another mentor has become a good friend. But for Robert, there’s no need to force a continued connection after the initial meeting.
“Most connections have been one or two meetings and have kind of served their purpose and petered off, which is how it’s supposed to go. You find some people who are the right long-term mentors, and then you meet some people and they give you information, and you do what you can do for them, and then move on to the next thing.”
Based on that, we’re going to define a successful mentorship as one that is productive for both participants and continues — or concludes — naturally.
Preparing for that first meeting
Let’s get practical. It takes more than good intentions to make a mentorship productive for both mentor and mentee.
Robert has some specific advice for getting value out of a mentorship meeting with a new mentor.
Be curious
Perhaps not surprisingly, given that he had selected mentors based on areas he was deeply interested in (whether as a career or as a general area of interest), Robert approached meetings with his mentors with deep curiosity about the day-to-day minutia of their work.
“I’d ask ’Hey, what’s a day like in your shoes? What’s a week like? What’s your year look like? What do you want the future to look like?’ They provided so many insights that you could never get, even from a book or a website or a google search — stuff you don’t get except from a real human being. Really I felt spoiled by it; it’s been so much good stuff.”
He gave some practical suggestions for incorporating his questions into in-person meetings.
“I bring a physical notebook, always, not my phone (you can’t have your phone out in a meeting — I just think that’s awful). Ahead of time, I’ll write down a question and I’ll leave some space to write down the answer. Usually I’ll have two or three pages of questions and only get through maybe four of them, because it just turns into a natural conversation, but to me preparation is everything.”
Do your research
Robert wasn’t just asking general questions that could apply to every job or every mentor. His questions were detailed, specific, and thought-out in advance. He goes into every meeting prepared.
“Find out anything you can about the person, anything they put out there that’s public facing — LinkedIn, Facebook, Twitter, Instagram. To me, if they put the information out there, you should know it.
“And if you don’t, you know, it’s probably going to be ok, but I like learning that stuff cause I think it’s a shortcut to a level of openness and intimacy and fun that you can have in your conversations with that person. If you know their alma mater, if you already know that they’re passionate about, say, animal welfare, you immediately have some sort of connection. You immediately have some things to talk about.”
Robert’s well-researched questions didn’t just help drive the conversation forward, they helped make it meaningful to both mentor and mentee.
Do as much work as you can for the mentor
In his mentorships, Robert takes on most of the legwork of scheduling meetings, trying to make it as easy as possible for the mentor to meet with him.
Asked what he’d advise mentors to do to make a mentorship successful, Robert said: “Just give whatever you’re comfortable giving and be fascinating, amazing people — which they already are.” And though he admitted that it’s a plus when mentors are “transparent about how they feel about the relationship,” he followed that by reiterating that much of the responsibility for setting the tone and doing the “legwork” of scheduling meetings should rest with the mentee.
But if the logistical legwork rests with the mentee, how should they handle that? Robert designs his meetings around the ask he thinks is most likely to work for the mentor.
“I like in-person meetings a lot; I like that you can be face-to-face, look somebody in the eye, and connect with them. But I don’t think there’s anything wrong with phone meetings, especially if it’s somebody who doesn’t have a lot of time and you want to make a really small ask — you might say “Hey, do you have time for 15 minutes on the phone.” That’s something that I think a lot of people may be more willing to do than an hour-long lunch.
“But I’ve found that people have been extraordinarily generous with their time. I went to see another mentor at her company headquarters and she gave me a tour, and Natalie I met at her company headquarters as well, which is this extraordinary, beautiful office space, and she got me food, and we just hung out for three hours.
“So again, I think that phone is good, but in-person is way more fun, and if the mentor is down for it, I think that’s the best thing. It gets you right to that point in the relationship where you really know somebody a little bit better.”
So should you get a mentor? Or be a mentor?
At the end of the day, mentorship is all about connecting with other people. As Robert put it:
“We live in this horribly disconnected culture in a lot of ways, and mentorship is a really wonderful ways to address that and connect older, more experienced generations in various fields to younger people who are interested in them. I think both sides are really longing for that type of connection, and I think it’s a thing that’s missing in a lot of people’s lives.
“The HW Works platform has definitely taken all the Harvard-Westlake School alumni offerings to the next level. I hope any young person who’s on the HW Works platform or involved in a mentorship program can get past any kind of intimidation and just try and reach out to someone and see what happens, or reach out to ten people and see what happens.
“And if you’re a mentor or if you’re someone who’s curious about what it’s like to pass on your knowledge a little bit, jump on there and put yourself out there, cause it’s a lot of fun.”
