Hindsight 2020: Reflections between Big Tech and Government
A candid deconstruction of 10 lessons learned from the other side of the aisle.
From 2018 to 2020, I took a civic leave sabbatical from Microsoft to serve a “digital tour of duty” as a White House Presidential Innovation Fellow (PIF). I leaned into government at a time when the digital demands of the 21st century seemed too big to ignore, and the stakes in our country felt higher than ever. Little did I know, 2019 would be an onramp, and 2020 would become the greatest modern-day test of our democracy — socially, politically, and logistically.
In hindsight, leaning into service was the best decision I could’ve possibly made. I’ve now wrapped up my fellowship and also officially left Microsoft. When people hear about my background, they can’t help but curiously ask about my experiences. This is my retrospective comparing the two cultures, and this is a follow-up to my original post on making the leap:
Here we go…
1. “Diversity” is not our biggest problem.
When I moved to DC, I began working alongside one of the most diverse teams. My PIF cohort consisted of 17 fellows. We came from different walks of life, socio-economic backgrounds, parts of the country, industry domains, and we were all at different stages of our personal and professional lives. There were only two things that connected us: being American, and showing up to serve.
Don’t get me wrong, there’s still plenty of work to be done on equity. But when I came into the office every day, I had the opportunity to learn from doctors to veterans. This was easily the most diverse team (in every possible way) I’ve ever been a part of — and that was truly refreshing coming from Big Tech.
2. Everything is at least twice as hard. It hardens you.
Below is a screenshot of a database I encountered during my time in government. I took the screenshot with a time stamp because I was in such disbelief that a system so archaic could still exist.
In another example, I once asked where I could find an org chart while visiting a field office. The staff member showing me around pointed to this whiteboard:
It had name magnets and was the only source of truth for the division. These are just two examples where federal workplace practices have never (like literally never) been upgraded or redesigned for productivity.
You’re also considered lucky if you’re set up with your laptop within 3 weeks (not kidding). Public speaking requests need to be submitted 6 weeks in advance for approvals, and it took me 4 months to get a software license for Balsamiq at my agency. Trust me when I say everything is at least twice as hard. But there’s a powerful silver lining to this.
If you can ship software here, you can ship software anywhere.
Government leaves no room for excuses. It shows you (and everyone around you) what you’re truly made of — as a product manager, as a designer, and as a collaborator. You quickly realize who can make lemonade out of lemons, and who’s faces are still wincing. It humbles you, and it hardens you. Also, if you’re the type of person to claim you thrive under ambiguity or love tackling big challenges, a stint in government will definitively test that… much more so than in Big Tech.
3. “The competition” is ourselves.
The Federal Government owns 100% market share of its civic services. Think about that for a moment. From a product perspective, you’re not fighting for a fragment of consumer market share within a segment. You may actually be the sole agency, owner, creator, and gatekeeper of an entire societal system — like the Census Bureau, or the IRS.
What might take you three months to ship in the private sector, may take you three years in government, but when it ships — it is instantly “a thing” and the impact is huge. There’s no growth team. You simply do your best, and when you launch — millions of people will depend on your product overnight. And while it might have taken you years to build, it may equally take decades to replace or dismantle. So with that in mind, you design much differently. You make different tradeoffs and take different calculated risks.
4. Success is defined differently.
One thing I love to hate, but hate to love about the private sector is the sheer clarity of the bottom line. Employees, managers, and shareholders are bonded by the one and only universal truth — we serve the bottom line. Because of this painfully clear objective, decisions can be deliberated objectively and strategically (and too often mercilessly). And while you can set user engagement metrics, or happiness scores, they all take second place to quarterly earnings.
In government, success is a much bigger picture on a very different timescale. They say, it’s easy to start things, but it’s hard to sustain them. Success in government is not merely about launching a campaign or introducing a new process — it’s about driving lasting systemic change. It’s about effectively building upon an enduring body of work. Success isn’t measured by dollars. Success isn’t confined to an annual review. One of my greatest successes has simply been telling my story and inspiring a few others to take the leap and join me along the way. Perhaps this legacy will make a more lasting impact than any of the work itself.
5. I miss the Corporate Kool-Aid and surprisingly, the reorgs.
I never thought I’d say this, but I really, really miss the Corporate Kool-Aid. As it turns out mission statements and inspirational quotes are critical in aligning tens of thousands of employees. Who would’ve thought?
In government, there’s often no shared vision or organizational alignment. Each division has their own interpretation of what “making a difference” or “being effective” means — and everyone is making localized decisions on what they believe is best. To make matters worse, the government is about 100 years behind on a reorg.
Job fields haven’t been updated since the 60’s, so you won’t easily find job descriptions that line up for modern disciplines like design, product management, or data science. The way the early civic tech movement has expanded is through a series of loop holes and hiring authorities to bring in more “IT Specialists.” This is clearly a problem, and many incredibly smart people are trying to overhaul it… but there’s still so much work to do here.
Looking back, I experienced 5 reorgs in my 5 years at Microsoft, and they were frustrating. Sometimes I had to change buildings, sometimes I had to change managers. But reorgs represented the act of housekeeping. We take out the trash, and rename our teams. Because they were so frequent, reorgs felt redundant, unnecessarily disruptive, and superficially political. But most often — the outcome was extremely clear. Like it or not, there’s now a new order and a new direction to execute against. In hindsight, I took reorgs for granted. I never thought I’d say this, but I think the greatest opportunity for impact in government might just be a massive reorg.
6. No one “owns” anything, and power is relative.
In the private sector you have an clear chain of command. If you have an issue, you escalate it to your manager. If your manager can’t resolve it, they escalate it to the director. If that still fails, it goes to the corporate vice president, and on the rare occasion, up to the CEO. In government, I expected this same pattern. To my surprise, decisions are made all over the place, and power is relative. Most decisions get made in middle-management and within each horizontal layer of ownership. You have tremendous soft power by owning the pen and making localized decisions in your organization.
7. You can’t tell what’s real.
In Big Tech, there’s usually a source of truth somewhere. Whether it’s a backlog in VSO, Asana, or Jira, there’s usually a Kanban board of truth. Every company adopts this practice differently — whether they’re Tickets or Tasks, Stories or Epics. The most valuable benefit of this process is having a centralized plan for what’s happening. But Government has no such process… so initiatives and agendas are scoped at every scale possible, and you can’t tell what’s signed off versus what’s an unbaked proposal. Remember Fyre Festival? Yeah, Government is kind of like that. Be warned about “this new major initiative.”
Not knowing what’s real and what’s fake makes your job twice as hard. And there’s also a limit to how much truth-seeking and report-finding one can handle, so at some point you begin exercising actions and decisions based on the imperfect information you have. It’s both terrifying and exhilarating.
8. Working with a pre-digital workforce.
There’s no easy way to say this, other than professional ageism is real. I was weirdly caught in-between two cultures that are diametrically opposed on whether or not age is a qualifier for what you bring to the table.
In Big Tech — the fountain of youth is powerful. Fresh grads are coveted, and new ideas are embraced. And quite frankly, everyone is a little panicked about when they will become irrelevant or when they’ll be lapped by the next wave of rising stars. In a competitive tech sector market, everyone is fighting for their products and their team to win. This means, we’re not actually in a space race for technology — we’re actually in a space race for fresh talent. And it shows. New hires are showered with swag, benefits, free food, colorful offices… and more. Every accommodation is optimized for the new generation — not the old one. Pictured above is my Microsoft Corporate Vice President in an Incredibles outfit. Those were the days!
Government however is the opposite. Years of experience is the hallmark of ability and earned respect. There’s a weird sense of people needing to “do their time,” and working up the ranks. This ideological clash was hard to miss, especially for me, as a young, Asian-American woman in a GS-15 role. I felt this bias towards age and seniority all the time. It created for a weird dynamic, but it taught me a lot about building trust, earning respect, leading with humility, and honoring legacy.
The ageism is bi-directional. On the one hand, young technologists are quick to dismiss the wisdom of baby boomers — an arrogant misperception. On the other hand, baby boomers have not done a good job preparing the next generation for the challenges they will soon inherit — a shortsighted reality. With over 30% of federal employees being eligible for retirement by 2023 (nearly one in three employees), we’re on the cusp of a monumental workplace shift. As it turns out, the biggest threat to our government may actually be ourselves… and the path to catalyzing digital transformation may actually be about catalyzing workforce transformation.
9. You know people are “here for the right reasons”
Age aside, there’s a profound bonding in showing up to serve. Whether you moved cross-country, took a pay cut, or both — there’s a baseline of giving each other the benefit of the doubt. Because no matter who you are, or where you’re from — it took sacrifice to be here. And that is a powerful foundation of trust that is rare to find in Corporate America. Technologists who show up to serve are not here for the bonuses or the frills — in fact, even the water is not free (literally). The buildings are seriously so old that they advise against drinking the tap water without a filter… And if you want in on the water cooler, you’ll need to hit up Nannette (instructions below).
As a millennial, there was nothing my parents could have said or explained to prepare me for this profoundly humbling lesson on workplace privilege. For tech millennials, capitalism has only done us dirty. And there’s always something to be learned when you put yourself in the position of others. I highly recommend it.
10. It’s not about you.
In Big Tech, it’s common practice to have weekly 1–1s with your manager. There’s also an expectation that this time is your time. Not time to discuss project updates or blockers, but time dedicated to discussing your career growth, trajectory, to solicit feedback, and talk about your personal plan. While not all managers are created equal, they have a vested interest in your career, and there’s institutionalized work put into growing each and every individual. Managers don’t have time for this in government, because… well, it’s not about you.
By the end of my first year in government, I experienced career ego death. For once, my career wasn’t about me — it was about being of service to everyone else. I was serving the US Department of Veterans Affairs (VA) when COVID-19 hit. The VA is the largest health care provider in the nation, and it serves as the country’s backup health care system during national emergencies. I spent my first year ramping up, building relationships, and developing a strategy — and by spring of 2020 there was no time for much else but to serve… To serve our country in its greatest time of need, to serve my teammates under greatest time of pressure, and to serve our Veterans in greatest time of vulnerability.
Putting myself in a position to serve others has had a profound impact on my worldview and approach to work. It gave me purpose during a time of crisis, and it grounded me during a time of uncertainty. I came to government with the intention to serve, and to be a part of something bigger than myself. I couldn’t have predicted or even imagined how 2020 was about to unfold. In hindsight, there might not be have been a more intense moment in modern history to see and experience (from the inside) how our government responds in true crisis. I got what I wished for, and so much more.
Your time to rise
This Friday, May 14th, 2021 is the last day to apply to the upcoming cohort of Presidential Innovation Fellows. I hope this article shed some light on the experience itself. Besides the challenges that come with the job, serving in the United States Government during COVID-19 has truly been one of the greatest honors and experiences of my personal and professional life. While I left this position to tackle other problems, I believe there’s never been a greater moment in time for technologists, innovators, designers, and leaders to rise to the challenge. It’s not for the faint of heart. But the reward is truly in the work — Apply today.
