John Korber: leadership without boundaries

In a sea of sharp minds, John stands out as the razor’s edge. In his Journey, we explore distilling the first principles of complex systems, driving cultural change in an organization, and how some of his greatest leadership lessons were learned on the ultimate frisbee field.

Sidebar:  So you grew up outside of Hartford, Connecticut, and you still live close by. Growing up, did you get any sense of how you fit into the world and what you were going to be when you grew up?

John Korber: I feel like, relative to many people, I didn't really have a lot of pressure to be a particular person when I grew up. Both my parents were educators and fairly gung-ho overachievers, which meant they were always happy to let us over-schedule ourselves. There was a big expectation that we go with the flow as kids, like “All right, we're doing whatever is next.” This parenting style helped me develop a broad set of interests and talents. In high school, I was comfortable in many different circles, and that's continued to be true in my professional life.

Sidebar: I love that explanation. From that type of upbringing, did you have any vision of what work might look like for you?

John:  I was always working on something. I was really into LEGOs when I was young, then later I became captain of my high school baseball team, then discovered working on my cars, then learning about computers and networks. I loved solving interconnected problems. As a kid I would have told you I'm going to be a mechanic or an engineer or a LEGO designer. It was only in the middle of my career that I figured out, “Oh, that's actually my thing – being able to understand and stack all these systems together, not being a technician in any one of them.” I understand the whole system of a problem by being curious enough to learn its individual parts.

Sidebar: You’re a man of many interests and contrasts – you have a CS degree and an MBA, you were head of technology, now you’re VP of strategy and innovation in financial services. Walk me through how you think about transformation.

John: I was like a lot of people picking a major, a little unsure. I wanted to be MIS (Management Information Systems), but Tufts didn’t have that, so I’m like, “Computer science, that’s probably the same.” By this accidental decision, I learned algorithms and software development and came out of college technically equipped to be an IT guy.  I quickly discovered that I didn’t want to be pigeonholed inside one discipline. I didn’t want to be responsible for the server room, I wanted to have meaningful contact and leadership in the actual business we're running.
So I found ways to leverage my technical acumen in valuable ways, by being able to talk about people and process and technology, all working in concert. I realized I have this rare, marketable brand as somebody who has expertise in all of those disciplines at the same time. In the financial services space, all three of those things are really, really important.
I also learned that my serious team sports leadership experiences were a big differentiator.

Sidebar: Right, so you are a serious athlete. You played baseball. You formed an ultimate frisbee team that got to the national championship game within a year. What’s your view on the overlap between sports leadership and business leadership?

John: If you put LeBron James on a basketball team with middle schoolers, they'd be the best middle school team in the country. But in ultimate, you can’t create your own shot, you can't run with the disc, you can't throw it to yourself. Ultimate is inherently dependent on the whole system, and the best teams possess a codependency, trust, accountability, and shared desire to get to the highest level of performance.
In 2022, we have distributed workforces and asynchronous work. Take two businesses with 10 people each – one’s going under and one’s producing $100 million a year of revenue. What's the difference? At a foundational level, how the team works together is probably the difference. The secret sauce to making a business work today is creating an environment where the whole is always greater than the sum of the parts.
In the sports leadership conversation, you want to hire high-performing athletes who've led sports teams, because they know how to get elite performance out of the collective group, not just be a team player.

“The secret sauce to making a business work today is creating an environment where the whole is always greater than the sum of the parts.”

Sidebar: That's a good segue into something you wrote on LinkedIn, “focusing on delivering results through culture change.” Culture change is hard. This is something a lot of great leaders struggle with. How do you think about it?

John: I think it's important to think about culture as a set of behavioral norms. I've had conversations with disappointed leaders who say, “We hired a new head of culture and we still seem to have disgruntled employees.” Although their new head of culture is probably a rockstar, until you fix the underlying behavioral norm problem, talking about culture is just words. If we’re not prepared for the hard conversations about changing our own behavior to change that norm, we’re imagining a culture change that just isn't going to happen. Changing culture requires a high level of self-awareness and serious engagement… and sometimes really uncomfortable, tough action.

Sidebar: Great answer. Okay, So you're a member of Sidebar, which means you're committed to being the best leader you can be, what's something you're working on with your group right now?

John:  The group I'm in is a bunch of ambitious problem solvers, and a theme that comes up often is – what role do I play in the problem that I'm bringing to Sidebar? My group has helped point out my blind spots and added more inputs to my problem solving algorithm.
The thing I value most about Sidebar is that I have this thought partnership group without any proximity bias. I can't describe a work problem to my wife without her bias impacting the input. I can't describe it to my coworker. I can't describe it to my boss. I can't describe it to somebody who works for me. I don't have anybody in my life I can solve these problems with.
Our group provides critical-thinking pressure testing, from an unbiased place that doesn't allow us to discount or compartmentalize things. In a lot of ways, that unlocks an approach to a problem that we might not have considered before. You see people's eyes light up. They're like, “That's great, I’m gonna solve this problem now, I'll report back in two weeks.”

Sidebar:  Can you think of a specific instance where your Sidebar group changed the trajectory of your approach in the workplace?

John:  There have been a couple of cases where I was more of the problem than I thought. I butt heads with a peer of mine on this one topic, and every time we seem to get somewhere, we get stuck and go around in a circle. I can't see why I can't convince them to see it this one way. And somebody in the group was like, “John, it's not a zero sum game, it isn't binary… here’s how you might think about it instead.” I’ve realized that my system-thinking brain very much wants binary solutions to problems, however systemic and complex. It probably is the kind of advice I’d give to someone else in my situation, but for whatever reason, it can be hard to see our own problems that clearly. And what's been really fascinating to me about Sidebar is that in a lot of these cases, we are giving each other advice that we would give to ourselves. That sort of support system has been invaluable.

“We are giving each other advice that we would give to ourselves. That sort of support system has been invaluable."

Sidebar: Such a great answer. So you have four children. I want to know your biggest piece of advice for other parents navigating career advancement with a family?

I would say throw out the paradigm of the work-life balance. Work is one of the things in your life – it’s what you do to generate income for you and your family… and it creates purpose. Just like being a parent is a thing in your life. I would encourage people to figure out how all their important things fit together, not how to balance your professional life with your non-professional life. Because it’s rarely going to be balanced, and you’ll go insane chasing that balance.
Here’s a story: yesterday I ended up with the responsibility of picking up my four-year-old daughter from preschool at 11:30am. We’re renovating our house and not living there currently, so I was like, “I'm going to bring her by the house because we haven’t been home in a while. We’ll go for a walk in our neighborhood. And I had to talk myself into giving myself permission to do that – I actually blocked off my calendar from 11:30-1pm… most of that time would be my lunch hour anyway. Why do I think I need permission for that? In what world do I have to feel bad about that being something I'm able to give her in that moment? A lot of high performing professionals very much need to give themselves permission for that.
Further, leaders shouldn't build a culture where you have to give yourself permission for that. In my senior role, if I'm so bold to feel like I can give myself that permission, what about my peers or direct reports who don't feel bold enough to ask for that permission? They're just leaving that upside with their kid on the table, and they don't even know it. Someday your kid’s going to move out and then you're not going to want that permission anymore. Part of my responsibility as a leader is to proactively create the space where that permission is assumed and doesn’t need to be granted.

“Part of my responsibility as a leader is to proactively create the space where that permission is assumed and doesn’t need to be granted.”

Sidebar: That is such a good answer. I think that will resonate with a lot of people. Can you think of any life-defining moments or epiphanies that have shaped you into the person and leader that you are today?

John: In high school, I decided it was a good idea to go to the US Naval Academy. I didn’t have any family history of armed forces service, but it felt like a great learning and leadership opportunity. I thought, “It's only a 10 year commitment, how hard could that be? And it's free.” Feel free to call out which of those things my 17-year-old brain might have underestimated. And so I went, and I was there for about a month, and I realized that there was no way to go through the motions for your own leadership development exercise. There is only one way – you fully drink the kool-aid as a member of the US Navy. It became obvious to me that I wasn't going to do 10 years for my own benefit; I was only going to do 10 years for the benefit of the US Navy and the United States. I started to feel like a bad teammate, like if I'm not actually serving my teammates here, not fully drinking the kool-aid, I should leave. It was emotionally difficult to leave, but I took a year off and worked full time. That year reinforced that I wanted to go to college… and that led me to Tufts.

Sidebar: How are you misunderstood?

John: Oh, that's a good question. I often get earmarked as being the expert in a particular vertical, but not the whole picture. I am good at understanding enough about any vertical to become fluent in it, which is great, but can have unintended consequences.
For example, I'm sitting in an electric car talking to you right now. All of a sudden I’m marked as the electric car guy. Which means when we have a conversation about transportation, I get this projected bias, like John’s going to have a green opinion about this.
Well, I also have a Yukon with a big V8 that gets 10 miles to the gallon. Hearing that, you might say, “Wait, I thought you were the electric vehicle guy.” Who said I was the electric vehicle guy? When did we decide that?
I just love a good solution to a problem. So when I have to tow something or carry my family of six and all of our stuff on vacation for a week, the Yukon is perfect. But I don't drive that to work because it gets 10 miles to the gallon. And I'm allowed to have both of those opinions because I'm a problem solver, not because I am a SUV guy or because I am an electric car guy.
So let’s stop silo’ing people.

Sidebar: John, we loved this interview and your passion. Thank you so much.

John: My pleasure.

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Identifying and Nurturing Your Team Culture