May 4, 2023
By Mari Megias
James Oliver MPP 2023 came to Harvard Kennedy School from Sydney, Australia, where he worked at The New South Wales’ Department of Education to improve outcomes for students. After his first semester at HKS, Oliver heard about the School’s Career Shadowing initiative, led by the Office of Alumni Relations and the Office of Career Advancement. The program pairs students with HKS graduates to help them gain insight into different career paths.
He chose to match with Joseph Olchefske MCRP 1984 in January 2022. A former superintendent of the Seattle Public Schools District, Olchefske now mentors emerging leaders, including HKS students. When Oliver met Olchefske virtually more than a year ago, he didn’t foresee that their relationship would grow beyond a meeting or two. Instead, Olchefske has continued to guide Oliver as he thinks about his professional future and how best to lead.
Below is an edited excerpt of a conversation they had a year after they first met.
James Oliver:
I remember getting the email about the networking thing. I saw Joseph’s profile and thought it was very interesting. He was a superintendent but came from a non-educator background, which is my background. [Oliver had previously worked as a consultant at McKinsey & Company.] So, I was really curious to hear what his journey looked like. I didn’t expect it to be much more than maybe one conversation. But Joseph very kindly offered to have more conversations and make it a bit broader, and that’s what it’s become.
Joseph Olchefske:
I do mentoring, particularly now I’m retired. A motivation on my part is I had very few people in my career that I could call on to get advice and counsel at key junctures, people who had been there and done that. So, I really felt like I could very consciously think of moments in my life where I needed a wise voice and I didn’t get one, and I had to DIY it more than I would like. So, just serendipitously, people have come to me and asked me to help mentor them, and they have become very deep and meaningful conversations. I met James and I think we hit it off personally, but also the juncture he is at in his life and his thinking about his career is similar in many ways to several people I’ve mentored over time. So, I really felt like my experience with these other people could add value for James.
James Oliver:
I actually think this was more beneficial than what I thought I was signing up for. Having the ongoing conversation makes me think whether there’d be more people who would benefit from something like this. Obviously, Joseph has limited capacity, but whether there’d be other alumni who would think about it more.
Joseph Olchefske:
I would add that the student has to be in a place to accept the mentoring, and that’s not obvious. Mentors ask you tough questions that other people don’t ask you. I think one of the strengths of James is opening himself up to tough questions. As much as there’s a certain skill of being a mentor, there’s a certain predisposition to be a successful mentee.
James Oliver:
Sometimes when you’re a student you feel like you’re bothering someone, and you read into not receiving a reply for a while. It’s like, “Ah, they’re busy, I’m sure lots of people are demanding of their time,” whereas Joseph has always been like, “You have as much access as you want,” and really followed up on that. I think that’s been unique, at least for me. Joseph’s been really pushing the conversation. He’s helping me to think about what matters and what’s next. His questions are, “What would you die for and what are you distinctly good at compared with people around you? And how can you find the middle of that Venn diagram?” That has been really beneficial, having a space to do that and a bit of a structure and pushing you where you need to be pushed.
The fact that Joseph is a graduate also makes it very real. He says, “I’ve been in your shoes. My friends and my colleagues and my wife [Judith Bunnell MPP 1984] have been in your shoes, and this is where they’ve ended up.
Joseph Olchefske:
The benefit of being my age, I know the career paths of a lot of people. A tip from a mentor’s standpoint: I make a point during every meeting to give mentees homework, that the work isn’t just the 45 minutes we talk on Zoom. I don’t know how to mentor you and give you advice until I know what you care about. That’s not something you talk about in a 45-minute Zoom call. So, I leave that homework and, okay, six weeks from now, let’s talk about that. And we probably had five email exchanges in that six-week period about what it meant. And then a different piece of homework was, “What do you think you’re better at than anyone in the world?” If you can get your mentee to say what they care about most in the world and what they think their truly comparative advantage is in terms of skills and talents, wow, you can go a long way with a conversation.
James Oliver:
Definitely. It’s very rare that you have someone who’s pushing you to think and championing what you want to do or think about in a workplace. Your boss might do that, but they’re invested for other reasons. I feel like I got very lucky. I don’t know, Joseph, have people asked you before? I feel like you’re a special case.
Joseph Olchefske:
I think my pieces of advice to the students would be, number one, only do it if you are motivated to do it. Be clear about what you want, number one. Number two, I don’t think you should be afraid to be demanding of your mentor. I think a good mentor challenges the person to think about their role and their purpose and their direction. And then, yeah, there are jobs that come out of that. So, I do think the students should be demanding, should go in knowing what they want. And if the mentor can’t give that, doesn’t want to give that, doesn’t know how to give it, that’s okay, you need to move on. But I think just being nice and having pleasant conversations is insufficient.
A good mentoring relationship is an emotional experience. I would say a third of my mentees have cried at some point in one of our sessions. Good. We’re down to something. If you’re at that level of emotion, that’s a good thing. So, I would say, yeah, you’ve got to be at a place where you’re getting value and it’s having impact and it’s moving you.
James Oliver:
I just think of how sad would it be if you spent two years at the Kennedy School and you didn’t walk away with someone who you’d say was a mentor-y figure. What a wasted opportunity, whether that be another student who’s older, or a professor …
Joseph Olchefske:
Well, and James, just to interrupt…. What you just said. I came out of two years at the Kennedy School without that relationship.
James Oliver:
I think it can happen quite easily because you get very busy in the subject, doing the stats. It’s obviously all important and there’s so much going on, all the emails that you get daily and all this stuff. But maybe it was just where I was at—I felt like these questions are things that you rarely get a chance to work on because you’re too busy with work, et cetera. I’m still constantly thinking about Joseph’s two questions. I know areas that I’m passionate about. But definitely thinking deeply about that and what it looks like and really making sure it’s going to be intentional.
I’m very passionate about helping disadvantaged communities through the power of education. I also have a really strong faith and I’m thinking deeply about how that connects and what that means.
Joseph Olchefske:
Well, let me add to that, James, I think getting at this issue of education and the value of young people growing into successful adulthood, for sure, and leadership and the capabilities James has around leadership and moving people is obviously a tremendously strong strength. But then he had an interesting aha moment where he saw in his education class Michelle Rhee [MPP 1997, former chancellor of the District of Columbia Public Schools,] speak.
Both Michelle and I have taken significant slings and arrows in our career and had enemies, opponents, and critics. That was a hard thing for James, that if you’re going to do something you’re passionate about, people are supposed to love you for it and feel good about it and applaud you. And seeing those two role models, I think, challenges James. And this is the question I wanted to ask you, James, is when you go out in the world with all this passion and all these skills, the world is not waiting to applaud you and send flowers your way. You’re going to have to do tough stuff. I feel like that’s one of the places we’ve left the conversation: how do you, as a leader in this space, accept, take advantage of, respond to confront conflict and opposition?
James Oliver:
It’s hard because we all have different views. If you’re not receiving any heat, you’re probably not actually having that much of an impact. So really digging into what that means, what that’s going to feel like, and realizing in myself there’s a bit of a bias to want to be liked, and that being one challenge, to think through that: that if I really care deeply, if I want to have an impact about things, inevitably there’s going to be some pushback.
Joseph Olchefske:
That’s a good tie-in between the mentoring and his classwork because that was Paul Peterson’s seminar course that I spoke in [Peterson is Henry Lee Shattuck Professor of Government at HKS and director of the Program on Education Policy and Governance], that Michelle Rhee spoke at, which I think gave James and his classmates some real-life examples of what it looks like on the ground when you’re going out and doing this stuff. And James, I think you owe me a call …
James Oliver:
I do, yes.