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Obama CTO Harper Reed on Keeping Sane in a High-Pressure Environment

Reed discusses taking an Internet vacation after helping reelect President Obama and other ways to decompress after a big project.

The 2012 Presidential Election, in some ways, was like every other election that came before it. There were last-minute political ads, experts making wide-ranging predictions, and a nation watching anxiously to find out who would be its leader for the next four years.

But after the normal pontificating, celebrating, and hand-wringing a completely new narrative started to emerge: the president was reelected, in part, because of a superior technology team, a dream team of Silicon Valley and startup veterans. A team led by CTO Harper Reed.

The high-pressure role was quite the change for Reed. In 2009 he was selling t-shirts as CTO of Threadless, an indie t-shirt e-commerce retailor. By late 2012, he had a played significant role in reelecting the President of the United States.

We spoke with Reed about going from the startup world to politics and what it was like to manage a massive enterprise like a presidential campaign.

The pace of the campaign was probably a little bit of a shock at first when compared to your time at Threadless. How did you adjust?

There was a point when I was like, “What’s this feeling? What is happening?” And my wife is like “You’re stressed out, chill out man, it’ll be fine.” And I was like, “I don’t understand.” Because at my last job [at Threadless], I built t-shirts. You are not stressed with t-shirts. I just had to change how I acted a little bit. I started looking for diversions where the diversion wouldn’t be affected if I stopped doing it, like playing Minecraft with my brother. So if suddenly there was an emergency or if I was very busy, I didn’t feel like I was like messing up something by quitting or not participating.

So when the campaign was over, I imagine it went from running 24 hours a day to zero. What was that adjustment like?

I realized that I was really addicted to information. It sounds silly to say, but I was addicted to the importance of the role. I worked with this great team to do the most important thing that I have ever done. So suddenly taking that away was like, “Hey, wait a minute, I’m still here, I still want to do this.”

I had days when I would pull my phone 50 times in one minute and there wouldn’t be any email. Then I realized: I’m not that important when I’m not the CTO. I’m just a normal kind of guy. I decided to spend the week without Internet as kind of a cleansing thing. I realized that people aren’t worried that I’m gone from the Internet. When I was gone, I got like four emails I needed to reply to, and then a whole bunch of shit that I didn’t read. That was really a positive experience.

I had days when I would pull my phone 50 times in one minute and there wouldn’t be any email.

Plus, breaks that like can act as way to help your mind accept you’re doing something new now. A little bit of before and after.

We are weird ego people. I don’t like to admit that but I think technology is a lot about ego. I think startups are a lot about ego. You see this a lot when people don’t know how to delegate. I had the same problem [with not delegating] in the beginning of the campaign, but then you realize that you are not as important as maybe you thought you were.

It sounds like you did not fully realize what you needed in your work life and personal life until you were under pressure.

Totally. From a self-discovery point of view, this was an amazing experience. Though, there is a point at which I was really, really stressed and I really didn’t know how to deal with it.

Why do you think you were so stressed?

Probably because we all think we are super-people. A friend of mine owns a restaurant in New York and she was talking about how her growth as a chef had 100 percent to do with delegation. She has two or three restaurants now because she finally learned on how to delegate in the kitchen. For me, delegation was not that big a deal. But I knew, if we fucked it up, we would not re-elect the president.

I don’t like to admit that but I think technology is a lot about ego. I think startups are a lot about ego.

Describe the difference between working at a startup versus a presidential campaign.

There is a duality there: you want to make sure that you are aggressively able to get things done and able to be agile. But a campaign is so much like a huge IBM-sized company. I had never worked in an organization that big. The challenge for me as the CTO was to ask: “How do we have that healthy disregard for reality that startups often have so that they can be agile and innovative?” I do not think we failed at it, but I do not think it was done as well as it could have been done. It’s incredibly hard. Think of all the corporations that want to be as fast as a startup, but can’t be.

In what ways did you manage the frantic pace of the campaign in both your personal life and with your work?

For sure, this was not your ideal work environment. We worked 18-hour days for a number of months with no break and that isn’t normal. From a professional standpoint, we had really good team dynamic that relied quite a bit on the “retrospective” meeting at the end of a project that allowed us to stop and say: “What was it like to launch? What did we do right? What did we do wrong?”

Since we were practicing kind of a startup ethos of iterative development, we could usually see immediately what went wrong and what was right, and it was incredibly valuable. Just being aware of how things are going, and talking about it quickly, I think is incredibly important.

Is that because a retrospective keeps everyone on the same page?

It’s not just that. People forget to acknowledge, that especially in technology, work kind of hurts. People have feelings and it is important to talk about those feelings and address them. If you’re in a room and you say, “Okay, we launched today. How do you feel about that?” Then your team says, “I did not like it when this happened. I struggled with it and I was little bit unhappy that we put down this task, but I was super excited about this.” We just had a conversation, a real conversation, about real feelings.

People forget to acknowledge, that especially in technology, work kind of hurts.

And if people feel neglected, especially when they are putting in 18-hour days, it’s not going to work out.

It allowed us to be very aware of what is going on and not have to beat around the bush when someone felt we were doing the wrong thing, it allowed us to be direct and helped everyone handle stress. One time, [engineer] Mark Trammel actually stood up in a meeting and sung the Frank Sinatra song “My Way” to make a point. And everyone in the whole team started singing along. It was really funny.

How about you?

How do you deal with fast-paced work situations?

Sean Blanda

Sean Blanda is a writer based in New York City and is the former Editor-in-Chief and Director of 99U. Find him on Twitter: @SeanBlanda.

Comments (5)
  • Danny Halarewich

    Great thoughts from Harper. He’s a smart cookie.

  • Joe

    The only reason he was reelected is because 52% of Americans are useful idiots.

  • Diana Larsen

    As a co-author of “Agile Retrospectives: Making Good Teams Great”, I am gratified to read that Harper found value in holding regular, ongoing retrospectives for his campaign team. Many teams benefit from taking the time for retrospective meetings to continuously learn about and improve their work.

  • Rabin Acharya

    Ego, a seed of Start-ups; and Inability to Delegate, a recipe of failure. I totally dig it.

  • Jeff Slobotski

    Great piece Sean – Harper’s the real deal.

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