Scheduling the President

Mastromonaco (right) meets in the Oval Office with President Obama and senior adviser Valeria Jarrett. Photo: Pete Souza

It wasn’t hard getting Alyssa Mastromonaco ’98 to agree to an interview about her experiences working for Barack Obama and as director of scheduling and advance for the White House.

The problem was finding a time when she wasn’t too busy to talk. Mastromonaco got a taste of just how hectic her job is when she tried to schedule something for herself. After I first reached out to her by snail mail, we settled on a date for a telephone interview.

We didn’t end up talking until about three months later.

We first had to postpone our interview when her daily meeting with the president was moved to the same time. No way I could argue with that; I have a healthy sense of my place in the world. On another occasion when we planned to talk, she sent an e-mail asking to reschedule: “I’m so sorry, the Nobel Peace Prize has made today completely insane.” I hate it when that happens.

For a couple of days, it looked like Obama’s visit to a Madison middle school last fall to announce funding for education reform would allow us to meet in person, but then Mastromonaco had to “bounce off the trip” to Wisconsin to plan a presidential trip to Asia. At this point, I think we both wondered if we would ever speak or if we were doomed to an eternal game of e-mail tag.

Two months later, the planets aligned and she called. But about thirty minutes into our conversation, she stopped short and asked, “Can I call you back in twenty minutes?” We didn’t speak again for another five weeks. In that time, Mastromonaco planned a surprise birthday party for First Lady Michelle Obama (“You’d be surprised how complicated that is … somehow we kept it all a secret,” she says) and traveled to Haiti to help coordinate federal agencies engaged in relief efforts following January’s massive earthquake (she was sleeping on the floor of the U.S. Embassy when an aftershock hit).

Through it all, Mastromonaco revealed herself as an enthusiastic Badger and hard-working public servant who learned many of the same lessons at UW-Madison that I did, including one of the most important: never give up.

Published in the Summer 2010 issue