This is the most powerful 30-year-old in Boston

His dream to play second base for the Red Sox didn’t work out. So Dan Koh became chief of staff for Mayor Marty Walsh instead.

Dan Koh at work at his City Hall office. —Jean Nagy / Boston.com

Dan Koh has achieved more by 30 than most people achieve throughout their entire career. In addition to an undergraduate degree from Harvard, and an MBA from Harvard Business School, Koh formerly served as chief of staff for Arianna Huffington and general manager of HuffPost Live.

The Andover, Mass. native talks about the path he took to his current role as chief of staff to Boston Mayor Marty Walsh, his hectic daily schedule, and the coolest job he ever had (hint: it wasn’t his current one.)

1. How did you end up with this job?

Koh: I got lucky – extraordinarily lucky. I had worked for Mayor Menino for a year before going to New York to work for Arianna Huffington. And when I was working for Mayor Menino, the chief of staff was a guy named Mitch Weiss. When Mayor Walsh was elected, he didn’t have a chief of staff candidate, and he asked Mitch for recommendations, and Mitch recommended me.

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We just immediately found commonalities. He said ‘Why do you want this job?’ And I said ‘I really care about the people of Boston.’ It was just a naturally flowing conversation. Quite frankly, he’s just a guy you can sit and have a great conversation with. He’s just so real. And I’d like to think I’m like that, too.

2. What drew you to him?

Koh: He came across as genuinely caring. As someone who is interested in public service, that aspect of people who are politicians in the best sense – and not in the sense that is now stereotyped in society – was really something that appealed to me. A lot.

I think a lot of people – whether you’re from a rich family on Beacon Hill or whether you’re from a working-class family in another neighborhood – all can feel some kind of commonality with him. We come from very different backgrounds. I was fortunate enough to have a set of parents who were both doctors. I was raised in an affluent suburb. I didn’t have a very difficult upbringing. I had a brain disorder, ADHD, but in terms of my economic status, it was very different from the mayor’s upbringing.

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3. What do you think voters see in him?

Koh: They think he’s genuinely doing the right thing for the city and that he doesn’t have ulterior motives. And in my conversations with him, late at night or on the weekends, or driving in his car, I’ve never once heard him saying something that would be equivalent to what you’d hear Kevin Spacey saying on House of Cards.

Every time I’m talking to him and he’s eating lunch, he offers me some of his sandwich, and I’m like ‘no.’ That’s just who he is.

4. You were only 29 when you took your job as chief of staff. How do you think being young has been an advantage? How has it been a disadvantage?

Koh: He didn’t think he had much literacy in the whole innovation community. So I think he saw I could bring to the table a set of perspectives he didn’t have. And I feel like I’ve been able to educate him on a lot of stuff. Uber is a classic example. He now has a driver, so Uber is not something he would use on a day-to-day basis. He says ‘Talk to me about Uber. What makes it so popular?’ and I can take out the app and show him. And it blew him away when he saw it. And he’s like ‘I completely get this.’

So those kinds of things, whereas the first brush would have been to listen to the loudest voice in the room, which might have been another constituency, he very much kind of relies on me to give him that education.

Koh uses his iPhone to keep track of a running list of things he needs to discuss with Mayor Walsh. —Jean Nagy / Boston.com
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5. You once said that early on you warned Mayor Walsh that you would make mistakes. Have you kept that promise?

Koh: There are millions of times where I forgot to loop in a cabinet chief or forgot to tell the mayor about something, or announced something inadvertently. I think most importantly in my role, you just own up to your mistakes as quickly as possible. I’m going to screw up. I have and I will again.

I think the natural knock on a young person in a job like this is: that he or she doesn’t have the experience to make the right decision, or that he or she compensates for that by being arrogant and throwing weight around in a way that’s not collaborative.

The thing I was most scared and most cognizant of was coming in and waving around HBS cases that I read, and saying ‘You need to do this. I read it in a textbook.’

6. What’s your average day like?

Koh: I’m usually up by 6. I look at the news clips for the day. Those are sent to me around 5. I’ll go onto the Globe and the Herald and Boston.com and read the top stories of the day. At 6:45 every morning, the mayor and I have a standing call where we talk about the news, reactions to it, responses, and plans. And then we come up with a general plan for the day – what we need to get done. From 7 to 7:45, I typically go to the gym.

At 8:30 every morning, I have a standing meeting [at City Hall] with the chief of policy, the chief legal counsel, the chief of operations and the CFO, where we talk about everyone’s concerns for the day, and also whatever I’ve talked about with the mayor. Then we come up with a general plan for how we think things are gonna go. So that’s from 8:30 to roughly 9:30. That’s my most important meeting of the day, because everyone gets on the same page. Depending on where the mayor is – he’s in and out three or four times a day … He usually leaves City Hall around 6:30 or 7. I usually stay for another half hour, wrap things up, then go home and have dinner. And then I’m back on email. Around 10:30 every night, the mayor and I have another call. Usually by 11 or 11:30, I’m in bed. Then it starts over all again the next day.

7. There have been a lot of portrayals of chiefs of staff in movies and on TV. Which is closest to your style?

Koh: There’s a deference you need to have to the executive. He’s the mayor. But I’m not doing my job if I’m not pushing back on the mayor. If I think he’s making a mistake, I need to say so. As the chief of staff, I think if you really feel strongly about something, you need to really not be afraid to push. Leo McGarry does that very well on The West Wing. There’s a certain amount of a professional relationship there, where he says ‘Yes Mr. President.’ I always call him ‘mayor.’ One hundred percent of the time. [But] if I called him Marty every time, he would not be fazed.

Having said that, when Leo McGarry disagrees with President Bartlet, he fights him. And I do that to Mayor Walsh. We rarely raise our voices at each other, but in a heated exchange, sometimes I need to fire back, because it makes that kind of long intense discussion come to a better end. And he didn’t hire me to have someone who just says ‘Get it done.’

8. Were you raised in a politically active household?

Koh: My dream growing up was to be second baseman for the Sox. I was in denial for a while. My dad was very active in anti-tobacco efforts. He was commissioner of public health in Massachusetts from ‘97 until 2003. He gave me the coolest job I’ll ever have. I was 13, doing sting operations in an unmarked police car, trying to buy cigarettes. I look young now – when I was 13, I looked eight. And I was astounded by how many people sold me cigarettes.

It inspired me. I learned there’s a reason why laws exist. And there’s a reason why advocates exist. There was a board of health meeting when I was 16. They were trying to decide whether to ban smoking in restaurants in Andover. I managed to raise my hand and said that I really thought we should be banning smoking. And in the end they banned it, and they cited my testimony as one of the reasons. I was like ‘Oh my god. I’m not even old enough to vote, and I’m affecting public policy.’

Koh in the Mayor’s office. —Jean Nagy / Boston.com

9. Voter turnout was incredibly low in the most recent city election; how do you get people excited and engaged?

Koh: I’m in this business — and the mayor is in this business – because we believe in what politics and public service can do to really help people in the most concrete ways. When someone gets a call from the mayor when their loved one dies. When the mayor refuses to back down from a lawsuit from Steve Wynn even though it would probably be easier for us to do that. That’s why I believe in government. We need to get the message out to people that that’s what we’re about, so that they make the time to vote, to be involved.

10. You’re one of the most powerful people in a city that has a reputation for racism. What are you doing to change that about Boston?

Koh: I think the mayor’s office can play a huge role. I think some of this is societal. I think some of this is historic with our history of busing and the riots and the memories that come from that. To an extent, as this generation becomes more influential in the city and the attitudes and memories from that generation tend to fade, I think that’s helpful. But the mayor is not relying on that to wait it out so to speak. He actually did two things to try to address this head on.

The first thing was internally looking at our staff, and understanding the diversity of our staff and where we need to go. The city of Boston is a majority-minority city – I think it’s 54 percent minority now. Our work force was about 39 percent minority. So the mayor hired a chief diversity officer in the city – the first one the city has ever had to really take this issue head on.

Second thing, externally, we have partnered with the Rockefeller Foundation. They have given us a large grant to hire a chief resiliency officer. Resilience is typically looked at as when a disaster hits, how ready a city is. We redefined it. Our disaster – metaphorically – was the race riots that we still are embarrassed to talk about. So the chief resiliency officer will facilitate conversations around the city about things like busing, and have proactive conversations that aren’t just Mattapan to Mattapan, or Southie to Southie, but Southie to Mattapan.

This isn’t going to fix things overnight, but the mayor believes that the more we really talk about the issues we still have and the lingering effects of the policies we used to have, the more we can continue to heal.

Know someone in Boston who you’d like to see featured in a future Q&A? Email me at sargent@boston.com.

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