What Obama’s Tech Startup Has to Teach About Adaptability

What Obama’s Tech Startup Has to Teach About Adaptability

USDS marketing chief and former head of marketing for Google X Janine Gianfredi shares her lessons on how to build adaptable teams, even in the most rigid and regulated environments.

On her first day at the U.S. Digital Service, Janine Gianfredi knew the team’s website needed an overhaul. As the agency’s de facto CMO and former head of marketing for Google X, Gianfredi needed to figure out how to tell the new org’s story in a way that would attract top technical talent away from Google, Facebook and the like. Sure, USDS had been hailed in Fast Company and elsewhere as President Obama’s elite startup squad building a better government with tech. But anyone who went to its website saw something much more bland and bureaucratic.

“We completely redid all the content — the language, the tone, the design — and we felt really good about it,” Gianfredi remembers. “But because this is the federal government, we had to vet every piece of content through multiple stakeholders – communications, ethics, policy – and there was a ton of debate on what was acceptable. Many changes were requested. We wanted to say no. We couldn’t. It was the world’s best exercise in adaptability.”

That word has become key, not only for Gianfredi, but for all USDS team members who often parachute into long-standing agencies (think the Department of Defense and Veterans Affairs) to shake things up and build new systems. Of course, adaptability doesn’t always mean being overruled. But it does mean listening, adjusting, and trying again in a very specific way — a way defined by learning and resilience. Used correctly, it’s a tool that helps you win over time and with grace.

“Every act we take at the U.S. Digital Service these days is an act of adaptability,” she says. “We thought USDS was going to be about the government adapting to new technology. But more than half of it is us adapting to the culture of government and how it works. A lot of process and policy is there for a reason. But we only find that out when we ask and push.”

This is a familiar experience for a lot of startups. Maybe it’s not government they’re dealing with, but it’s certainly the culture of often monolithic industries they’re trying to change — whether it’s energy or banking or even food service. It’s doubly true for companies operating in regulated environments. “We have to adapt to what’s already in place in order to push it forward,” says Gianfredi. “Adaptability is being told no and figuring out what’s next. It’s not just about beating your head against the wall. It’s asking why the wall is there. What’s it holding up?” In this exclusive interview, she draws on her experience working at the White House, to offer all startup professionals a clearer window into what adaptability means and how you can cultivate it in your own companies and careers.


The first step to building an adaptable team is to isolate the qualities of adaptable individuals. Because USDS depends on technology professionals serving tours of duty sometimes as short or three to six months, Gianfredi has seen a breadth of people come through and either adjust flexibly or not — allowing her to build a profile of adaptable professional.

“Surprisingly, the number one quality is that they’re stubborn — or, as you might put it, determined to the point of stubborn,” she says. “They’re the person who tells you that there’s a solution to every problem. In an interview, they’ll use words like that. Uniquely, they might not know what precisely needs to be done — but that can be good because they aren’t overly committed to one path. They know there will be dozens of hurdles, but they never let go of what they’re running toward.”

Stubbornness manifests as an unwillingness to give up. This doesn’t mean it has to always go their way, or that they’re uncompromising. Rather, they’ll bend and change course in service of the North Star that they’ve selected for themselves. They’ve been able to clearly articulate what the end objective is and why they’re passionate about it. They’ll do what it takes to get there.

Adaptable people have to be optimistic. I don’t think anyone who’s adaptable lacks this trait.

“Why would you keep struggling so much if you didn’t believe in your eventual success?” Gianfredi says. “Look for people who believe in themselves and their goals so much that they’ll tell you, ‘Of course there’s a way.’ It’s not just that they believe in their solution, they believe in their own ability to come up with another solution that will get the job done.”

When interviewing for adaptability, you want to look for this type of self-belief reflected in past experiences. When did the person forge ahead with a plan against the odds or when it was risky? When did they assume responsibility for the success of a project because it mattered to them so much? When did they take on a leadership role because they trusted themselves to do it right? Ask them these questions. Adaptable people will have top of mind answers that showcase not only their self-belief, but the awareness that that was crucial to their success.

“Adaptable people are incredibly supportive of others — they do it because they want to, because they derive enjoyment being helpful, and without need for reciprocity,” Gianfredi says. “If you want to build a team that can pivot and stay nimble and recover from failure, you need to stack it with people who have demonstrated above and beyond support of colleagues or friends in the past. Working on a team like this means that people have to spend a lot of time picking each other up. They have to spend a lot of time listening to each other about how bad that meeting was, or how frustrated they are or what went wrong that day. It has therapeutic value that fortifies everyone. It’s something I see every day at USDS — not people complaining, but leaning on each other in a way that makes it possible to get out there and do it all again tomorrow.”

This level of support also cultivates trust — another must if a team is going to adapt successfully. People can’t be tripping over each other. They can’t be wasting time on territorial disputes or political concerns. They have to be able to divide and conquer, and trust each other to do the best possible job. “The key to this is to let people share their successes and failures in a way that’s not overproduced,” she says. “When you make a big deal out of it, it seems less genuine or less honest. Carving out more unstructured social time, where leaders set an example of confiding in the team about their wins and losses works the best in my experience.

The only way someone is going to adapt to their own wins taking months or years, is if they know that’s how it went for someone else they really respect.

Adaptable people gravitate toward diverse teams. And this doesn’t just refer to race or gender. It means a variety of backgrounds, family structures, childhood experiences, educational pedigrees, former industries. They generally like being pushed out of their comfort zones in a way that changes their view of the world and forces them to accept new thinking. They like to be challenged by the unknown and nudged out of their status quo. Being in an environment with people radically different than themselves reliably delivers this experience.

Again, if you’re looking to hire adaptable people, you might ask in an interview: How diverse have teams you’ve worked on been? How were they diverse? (You want people to recognize the influence of disparate backgrounds.) When did your colleagues challenge to accept different points of view based on their personal experiences and what did you think of that? When have you been pushed the farthest outside your comfort zone in a work context? When has someone else’s perspective meaningfully changed a strongly held opinion of yours?

If you’re running a startup, you dwell in a reality of constant change. For most people, this is really exhausting. It requires constant revision of beliefs, habits, ideas. Your goal as an organization should be to build teams that find constant change to be exhilarating — not scary or tiring. Do they gain energy and momentum? Do they expand and brighten? Or do they contract and seem more deflated telling the story?

Janine Gianfredi

Lastly, adaptable people practice in their personal lives. “Usually, it’s a positive indicator if we’re talking to someone who said they taught themselves how to code or to cook or to rock climb,” says Gianfredi. “For me, it was yoga that challenged me to do something regularly that I hadn’t done before and to push my boundaries just a little bit in my everyday life. People who do things where they regularly fail and try again outside of work — they’re much more likely to adapt. It seems like a small thing, but gradually, you’re normalizing being flexible, being okay with discomfort, trying new pathways to the same destination.”

The cool thing about this quality, is it’s also a tactic for growing your adaptability if that’s an area you want to work on. It might not seem like fixing bikes or trying to do a longer handstand has anything to do with your ability to be gritty on the job, but you’re using and exercising the same neurons. Doing one in your personal life will strengthen your ability to withstand pressure and innovate in the toughest of quagmires at work.


There are three things that Gianfredi has seen kill adaptability stone dead faster than anything else:

Hierarchy. This one isn’t so surprising, and it’s clear how she’s discovered this, having come up against government bureaucracy at its thickest and least wavering. But she also believes this happens at startups much more easily than people think, and before anyone notices. To keep pernicious hierarchy at bay, she recommends looking out for these early warning signs:

  • Your CEO has become more of a persona than a person. People poke fun at or commonly discuss only his or her key traits, without real knowledge of who they are or what they care about.
  • People are less approachable. You or your colleagues find yourself hanging back from going up to someone in person, or fish for any alternative to asking for help.
  • More people start troubleshooting on their own rather than casually socializing problems with their teammates or friends to find a quicker answer. This happens because they feel like they can’t afford to be wrong or they’ll lose ground in their org.

Slowly but surely, hierarchy squeezes adaptability out of any team. The culture becomes brittle as people become less risk averse — afraid of losing their place in the pecking order — people know and trust each other less to come up with collaborative solutions, and they stop valuing the reward of good ideas or problem solving over material or professional gain. It’s a killer.

Conflating process with bureaucracy. They aren’t the same things. “In order to be anti-bureaucratic, a lot of small companies and orgs throw away all process. They say they don’t want red tape, they’ll just stay flat,” says Gianfredi. “What they don’t realize is they’re often making their lives harder than they need to be.”

Bureaucracy refers to unnecessary rules that flow down an organization without adding real benefit. Process can offer massive benefit.

For example, documenting tools people should use and methods that have been proven to work can accelerate a lot of productivity, reduce duplicative efforts, save time, and more. Office hours and stand-ups, when conducted in this spirit, can do the same thing.

“Remember, adaptability takes a lot of energy — you have to be actively conscious of preserving your team’s energy so they can adapt,” she says. “A lot of process can be used to cut out steps and make things clearer to save a lot of this energy.”

USDS saw this play out in extreme fashion. Of course the knee jerk reaction to working with the federal government was to avoid bureaucracy at all costs. Whenever anyone proposed a new system or process for escalating issues, or even the simplest of policies, there’d be a backlash. Gianfredi agreed to a large extent, until she saw the need for process in action.

“We’re a lot different from other government agencies in that we love our team members to talk about what they’re doing all the time — at events, to the press, on Medium. Honestly, I’d love to see the government put more real people forward to talk about why they value their work,” she says. “But I did realize how hard this was to organize.”

In short order, she learned there needed to be a balance between stringent talking points and radical candor.

“So we started writing down rough rules around when someone should speak or publish, how they might express interest in it, and how they might get the support they need to feel comfortable about it,” says Gianfredi. “Yes, it was definitely process. Now we’re at a point where people need approval before speaking or publishing, but it actually saves everyone time. No one has to be scared. It made life easier.”

Don’t make bureaucracy and process synonymous. You’ll be cheating yourself out of efficiencies you don’t even spot yet, because you’re ironically so locked into a mentality of remaining “flexible.”

Saying nothing after ‘no.’ U.S. Digital Service. employees hear this word a lot. Government projects are complicated, with many interdependencies – things change a lot, and the team experiences pushback regularly. Their first recourse, naturally, is to not take no for an answer and try to push ahead another way. But sometimes a ‘no’ stands firm. This can be crushing, but it doesn’t have to mean total failure with zero gain. Adaptable organizations always make sure something comes after ‘no.’ Most of the time, this should be a credible, complete answer to the question, “Why?” Fortunately (and perhaps surprisingly), this actually does happen at many government agencies.

“Sometimes when we get told no and ask why, the answer is really really good,” says Gianfredi. “We work with people who have been in government for 30 years, but they’re also reformers trying to get stuff done. They’ve just seen a whole lot and know what works and what doesn’t. So we have to really listen and seek to understand. The worst is when we don’t even have the chance to ask ‘Why?’”

You want to build a team where it's always possible to get back to the source of a decision.

It can be even harder to clear a pathway to "why" at startups. Everyone is moving so fast. Time is scarce. There’s no room for asking questions. Just accept the no and move on, people think. This isn’t good and it will start hurting your ability to adapt. People have to be able to get to the source of a "no," fully understand it, and determine whether they can approach from another angle.

On top of that, sometimes even questioning a "no" topples it. Maybe it was based on a myth, or on "the way things were always done." If you can tear down false reasons for "no," you’ll have increased your org’s adaptability by an order of magnitude. If anyone at your company says there’s no time to ask questions, especially "Why," that’s your canary in the coal mine. Make sure there’s always at least one conversation after "no."


So now you have adaptable people, and you know what to watch out for, how can you create an environment every single day where adaptability is celebrated and thrives? Here are the attributes that Gianfredi has seen adaptable orgs have in common:

They have great documentation of what went wrong.

“If people in your org can point to the things, the moments, the decisions that didn’t work well and what happened afterward — how everyone recovered, or figured out a different way or got around something — you’re in really good shape,” she says. “If, on the other hand, everyone is just positive and you’re only dissecting the wins, you’re not helping yourself.” Whenever something goes wrong or fails spectacularly, investigate and write it down. You’re giving the future of your business a blueprint for how to be flexible and adapt to the next stage.

People ask questions at inappropriate times.

This is really a bellwether for whether you have a rigid or inquisitive culture at work. Don’t look only at how often people ask questions, but actually when. Are people so comfortable being curious and questioning authority that they’ll interrupt a staff meeting or blurt something out during an All Hands? This is actually a sign of health, of people proactively pushing back and wondering how things work. “Start counting the number of questions that get asked in your regular staff meeting, and set a threshold for yourself,” says Gianfredi. “Is this number fluctuating? Make sure it doesn’t go down over time.”

Employees have ample opportunities to stretch their minds outside of work.

This doesn’t necessarily mean some crazy offsite where everyone has to learn to potato sack race or garden. In fact, groupthink activities like this don’t fit the bill. Instead, you want to give people the time and space to pursue hobbies they individually value. “This is something I really respect about the culture at USDS People work really hard, but they have boundaries and feel like they can pause and have something else significant that they’re working on in their lives.” This maps to firing up those neurons of adaptability mentioned earlier. The best environments encourage goal setting and pursuit outside the office.

They have values that point to the next step.

This dovetails with having something come after ‘no.’ Too many startups create a list of “core values” that simply reflect the qualities they like their employees to have. But creating values is really an opportunity to help guide people through the way you want them to make decisions and adapt to situations that arise. For example, the U.S. Digital Service values are:

  • Hire and empower great people.
  • Go where the work is.
  • Find the truth. Tell the truth.
  • Design with users, not for them.
  • Optimize for results, not optics.
  • Create momentum.

Each of these serves as a signpost keeping people on course if they hit a roadblock or closed door. It all starts with hiring the right people who are passionate and motivated to do the work. But, for example, if you have a hard time getting to the cold, hard truth of a situation, the next best step is to look to end users and what it is they truly want. Then, the best way to serve them is to keep positive outcomes for them in mind, not how it will look otherwise internally or externally. Lastly, the value to “create momentum” reminds everyone to stay biased toward action even if the inertia of working at the federal level can seem overwhelming. There’s always new ways to create momentum and break new ground.

We want our values to remind people what they should do next to keep moving forward.

Photography by Joni Cooper.