Working Forward: Ross Dakin, Senior Advisor, Microsoft New York

From waiter to White House — it’s all about people

My first “real job” was at a local Italian restaurant in San Diego, where I bussed tables for three years during high school.

On my first night of work—having no experience—I loaded a tray full of eight water glasses, walked over to a table, and spilled them all onto a customer’s lap. I was devastated; I knew I would be fired.

Later that night, Javier (the restaurant owner) approached me in the back of the restaurant.

“What do you do when you fall off a bicycle?” he asked.

I paused, wide-eyed, then replied, “Get back on?”

With a nod, Javier walked away, and that was the end of it. To this day, he remains a mentor and one of my closest friends.

That job taught me so much about effective leadership, team dynamics, engagement with the public, and—above all—how to treat women and men working long hours in the service industry with respect and an appreciation for the distinction between “server” and “servant.”

Everyone should work in food service at least once—I’ve found no better lesson in empathy.

Technology is easy; culture is hard

Fast forward a couple decades—last year, it was my honor to serve as a White House Presidential Innovation Fellow in Washington, D.C., where again I found service and empathy to be at the heart of my job. This program (affectionately abbreviated “PIF”) was created to provide an avenue for bringing modern methodologies and best practices from the private sector into the federal government.

While there is a technology flavor to the PIF program, its greatest strength lies in the beginnings of culture change that it has brought to the federal workforce (agile development, human-centered design, an embrace of failure and an appetite for experimentation, etc.), and the key to changing that culture has been the employment of deep empathy for career federal employees. Understanding their procurement, budgetary, and security requirements helped us best facilitate the shedding of the business-as-usual mindset (“but we’ve always done it that way”) in favor of an open-minded curiosity for novel and alternative approaches.

One manifestation of this was the warming of government to modern cloud technologies despite unfamiliarity and natural skepticism. By empathizing with their encumbering bureaucratic constraints, we (and our friends in 18F, USDS, and other groups) were able to help many agencies navigate their way toward adopting cloud services for their technical needs. It’s been very encouraging to watch more and more agencies trust their missions (from food stamps to national security) to Azure and other cloud service providers.

None of that would have happened without first building trust and understanding between our group and the civil servants with whom we worked—it all starts with people.

The real heroes

As a side note, I cannot overstate how amazing career government employees are. The vast majority of everyone I met during my time in D.C. had the highest levels of work ethic, integrity, and true passion for public service. While participants in programs like PIF, 18F, and USDS perform short-term “tours of duty” to help modernize government (sometimes in highly visible ways), the career government employees of all levels who dedicate their lives to public service are very truly deserving of the highest praise and recognition.

The challenges I mention arise from the fact that our government is an enormous organization that necessarily has many regulations unique to the charter of providing for every single person in our country, often requiring stability that results in a natural isolation from the ways of the ever-evolving private sector. In this and other respects, it was very illuminating to appreciate the critical differences between running a business and running a nation.

Speaking of business

Many PIFs remain in government after their fellowships end, either as White House advisors, at other technology-focused groups like 18F or the US Digital Service, or within executive agencies in such roles as Chief Technology Officer, Chief Data Scientist, etc.

I opted to return to the private sector because I realized that it’s just as important for people with government experience to be in private companies as it is for people with private sector experience to cycle through government. When both sides of the table share experience with each other, we can begin to collaborate from a place of common understanding and accomplish much more than we could accomplish without the benefit of having gained insight beyond our respective silos.

This continues to be true for me personally, as my time as a PIF informs my current role at Microsoft a great deal: they share many attributes (both are small groups within large organizations, both are undergoing periods of reinvention) and their associated challenges and opportunities. While not public service, the Microsoft TCE team strives to generate public good in many of the same ways that I did as a PIF (identifying strategic partnerships, leveraging our unique scale, employing best-of-breed technologies, etc.), and I am grateful for both the opportunity to have served in my governmental capacity and to continue applying the learnings I gained there in the private sector.

Stronger together

Both my time as a PIF and with Microsoft TCE have opened my eyes to many astoundingly unfortunate conditions that exist in our country. The fact that 19% of American kids grow up in poverty is unacceptable. It’s 2017—we can do better.

This is why private sector programs like Microsoft’s Tech Jobs Academy, public sector initiatives like #CSForAll and TechHire, and public/private collaborations like The Opportunity Project excite me so much: the keys to economic advancement should not be the zip code you grew up in or being of a privileged demographic, but a strong work ethic and the daring to chase big dreams.

Both public and private sectors share a role to play in advancing economic opportunity, and the most progress can perhaps be made when they function together in collaboration.

Success and humanity

With the shared responsibility of generating public good comes a shared challenge: what is “success” when the goal is not simply to make money?

If we impact the lives of 10 people, have we been successful? Must we impact a thousand people to be successful? A million? What depth of impact is required to achieve success? How should we quantify the level of impact?

These are questions without right or wrong answers. They’re questions that are highly subjective in nature. When much of a technologist’s career involves black-and-white programming, these questions present an interesting gray area that must be navigated with an element of gut feeling, ethics, and intuition that a computer cannot provide.

This is the human side of technology—it’s truly all about people.

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