Tackling the Tough Stuff: a Conversation with Mikey Dickerson, U.S. Digital Service


Anyone in the events industry can sympathize with Mikey Dickerson. As a member of the U.S. Digital Service, he specializes in fixing high-visibility problems — and tough ones at that. He shared his experiences simplifying technology challenges for the Federal government November 12 at “Yahoo Digital Democracy: The Yahoo News Conference on Technology and Politics.” During an onstage conversation with Yahoo journalist David Pogue, Dickerson discussed what it was like to turn around the troubled Healthcare.gov website in 2013 and 2014. Although he is a member of a governmental organization, his insights about fixing a visible problem also apply to anyone who produces high-risk events.

During his lively conversation with Pogue, Dickerson described how his life as a Google executive changed with one phone call in 2013. U.S. Chief Technology Officer Todd Park asked him to travel from California to Washington, D.C., to help fix the Healthcare.gov site that had faced withering criticism for being a dysfunctional mess.

“Thank you so much for helping,” Park said to Dickerson before he had even agreed to help. “Can you get on a plane tonight?”

The opportunity to help fix a massive problem that was affecting the lives of millions of Americans seeking healthcare was too compelling to resist. Dickerson flew out to Washington for what he thought was a three-day project. He ended up staying for months before deciding to become a member of the U.S. Digital Service, which acts as a SWAT team to addresses technology problems and improve public service sites.

The U.S. Digital Service has taken on immigration, education, Social Security, and Veterans Affairs. The service was responsible for the recently launched College Scorecard, which helps students evaluate their most appropriate higher educational choices. During the conversation, he shared some of the lessons learned fixing the Healthcare.gov site (and other sites) over a period of months:

  • Too many cooks in the kitchen can cause a disaster. When asked why Healthcare.gov faced dire problems when it went live in 2013, Dickerson indicated that the government had hired too many companies — as many as 50 — to build the site. “You can’t hire 50 different companies to do 50 different parts of the job,” he said. Having too many partners on the project created needless complexity and a poor user experience. Certainly anyone who has produced events can relate to this lesson learned. Although big-time events require a diverse staff of experts to pull off, partnering with too many specialty firms can create accountability issues, lapses in communication, and quality control problems. The key takeaway: Keep things simple.
  • When a big problem happens, you need to prioritize. Especially when he was part of the team to fix Healthcare.gov, Dickerson faced an overwhelmingly large number of problems, ranging from bugs in the back-end system to an overall confusing user experience. He had a team of designers and coders ready to address those problems. His first step was to rank the issues in order of priority and start assigning his team accordingly. For instance, the initial login experience was assigned highest priority status: not only was the login a person’s first exposure to the site, but also its clunky interface was a public symbol of the site’s shortcomings. Here again, anyone who produces events can relate. We always strive to keep glitches backstage. And when a problem arises — say a speaker is a no-show or a technical glitch strikes — a team needs to act not only quickly but also correctly.

Mikey Dickerson was not only an engaging conversationalist but also a compelling one. He exhibited a commitment and passion for solving problems that affect how people live. “Working for the U.S. Digital Service is an opportunity to solve big-time problems, which is a different kind of reward than selling ads,” he concluded.

For a complimentary 30-minute consultation on how to build your brand and inspire an audience through events and communications, please contact Brian Duffy by calling 630.427.4235 or by emailing bduffy@onesmoothstone.com


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