What about the worst-case scenarios--what you've called "boil the ocean" projects that never get done?

The way information technology is budgeted is two years out. If you look at agencies right now, they're probably working on their 2014 budget for information technology. Yet the way technology moves is so fast that in two years you'll probably have a next version of the iPhone or Droid or BlackBerry.

Because there is this structural problem of how budget is allocated, agencies try to "boil the ocean." Their view is "If I'm going to get one bite at the apple every two years, let's try to do everything at once."

I think procurement in the federal government is broken. It favors incumbents and the status quo over the lean start-ups in terms of its archaic procurement rules and regulations. Most start-ups will tell you they will never come to the federal government and bid because they would go bankrupt trying to understand the procurement process.

Procurement is worse in federal IT?

Congress funds it bureau by bureau, department by department, agency by agency. So you have these sort of vertical lines of funding where IT is most efficient horizontally.

The one area where I wish we'd made more progress was with Congress on actually reforming that. Imagine if we had a committee of technology within Congress that would appropriate centrally. That would be the biggest game-changer in federal IT.

Did you have a problem with individual employees wanting to stick with the obsolete systems they knew well?

What was happening was the opposite. People were asking the right question--which is "If I can get on Expedia or I can get on OpenTable and it takes me minutes to do this, why does it take me half an hour to book a flight on this e-travel system we have within the government?"

That's the "shadow IT" phenomenon you've talked about--workers resorting to consumer tools to get their jobs done.

I think it's a factor everywhere--federal, state, county, city, you name it, even Fortune 500 enterprises. They're all going through it.

My view is that most organizations should get out of the business of issuing end-point devices such as computers and smartphones. That's why I've advocated for a cloud-centric architecture, where security should be at the cloud level.

What is it about IT that makes people complain about it so much?

In psychology, there's this principle of locus of control. Essentially, as humans, the more you feel you have control over your decisions, the happier you will be. What happens is that a lot of users hate IT because they're forced to take these vanilla boxes.

There's no competitive advantage to forcing people to standardize. Imagine if you could just say, "Here's a stipend of $1,500--go buy your laptop, go buy your mobile device, go get whatever plan you want."

Where does your interest in government come from?

I went into government because I wanted to have an impact and I believed there was a way to really drive change with information technology within the public sector.

I am actually not one of the people who are pessimists when it comes to government and technology overall. I believe that there's some amazing stuff happening.

You haven't spent too many years in any one job. What's led to that quick turnover?

It's the approach to the job. What I mean by that is that when I took the White House job, there were two ways to do it: treat it like a marathon over a course of multiple years or treat it like the race of your life. At the White House, I was showing up at 4:30 in the morning, leaving at 10 pm, and doing that pretty much every day except Saturday.

You had to work Sundays but not Saturdays?

Not Saturdays--I took Saturdays off.

Between your tenures in Arlington and in Richmond, you worked at a start-up, Evincible Software, and then founded and ran a small shop called Creostar. How do you compare working in the public and private sectors?

It was an amazing experience to be part of a start-up and to try to build within the private sector. At the same time, the public sector's potential scale of influence and impact is unparalleled.

I would imagine that at many meetings you've been the youngest manager in the room. Did you encounter any tension from that?

I remember walking into each of those roles, and I was definitely the youngest person in the room.

In my first set of meetings when I was in Arlington, when I was sitting down with other CIOs, there was probably a sense of "Well, we've worked in this role for 30 years or so. Who's this new person coming into this role and how is he going to drive or tell us what to do?"

My approach to that was to roll with the assumption that at the end of the day it's not your age, your ethnicity, or your sex that matters but your performance. I always doubled down on making sure that my performance would speak for itself.

How do you assess the health of the Washington tech industry?

If you look at what's happening in Boston and Austin and you look at the Bay Area and then Washington, the reason you don't see as much innovation on the Washington side is because of the way the government buys large-scale technology.

Venture-capital and private-equity guys will tell you they encourage all their start-ups to stay as far away from government as possible. The sales cycles are too long, and they basically burn all their VC money trying to go after one contract.

What have you learned about change and how people resist it?

It's very much like the human body. Change is viewed as a foreign object or a virus, and all the white blood cells in your body attack it. People are very, very comfortable with this notion of continuing the status quo.

At the same time, a lot of people don't realize that one of the fundamental laws of physics is that everything moves toward entropy, toward disorder. So you have an impact--but in order for it to be sustainable, you've gotta make sure the pressure continues.

This article appears in the May 2012 issue of The Washingtonian.