It's About Time:Every Second Counts When You're Obama's Scheduler

By Shailagh Murray
Washington Post Staff Writer
Monday, December 22, 2008; C01

A week before the election, Alyssa Mastromonaco was sitting at her desk at Chicago campaign headquarters, watching Barack Obama deliver a speech in Chester, Pa.

Uh-oh, she thought. It was pouring rain and the boss was shivering. As Obama hurried offstage, his trusty "Ms. Fix-It" started to count: Five, four, three, two . . . ring!

"Who thought this was a good idea?" Obama barked into Mastromonaco's ear. She tried to reassure him that at least the footage looked terrific, she recalled, "and then he hung up on me."

Mastromonaco can't control the weather, but she can handle just about anything else. Obama's campaign was a marvel of strategic logistics, with an upbeat former high school band president as its chief engineer. For two years, under every conceivable circumstance, Mastromonaco kept the planes, trains and luxury buses -- always ESPN-ready and stocked with organic tea -- running more or less on time.

The 32-year-old improvisational ace booked Obama's cherished gym sessions and organized the huge rallies that became the campaign's trademark. She compiled guest lists for backstage visits and determined whose phone calls would get returned. She kept Obama's secrets and took his grief.

And now Mastromonaco, who once studied French, Japanese and Bernie Sanders at the University of Vermont, is heading to the White House to be Obama's official gatekeeper there. Her title stays the same -- director of scheduling and advance -- but the job is infinitely more complex and more confining. Like other campaign aides who are making the transition, Mastromonaco is bracing for culture shock.

"We were so efficient," Mastromonaco said. "That's why the government feels a little weird right now."

Working in Chicago the past two years after decamping from Obama's Senate office, Mastromonaco, who's single, commanded a corps of savvy young people who made big things happen fast. She patched together flights and call lists via BlackBerry with a few hours' notice. Mastromonaco had weeks, not months, to plan Obama's overseas trip in July, an ordeal that involved eight advance teams and 15 events in five countries -- with no official U.S. government help.

If she thought Obama's delivery was flat, or that he was neglecting a certain constituency or issue, she told him so. Likewise, when the candidate started to slump, he could lean on Mastromonaco to make adjustments, so he could sleep more or stop by Chicago to see his family.

"When he thinks his life is out of control, or there's too much going on, he calls Alyssa," said Pete Rouse, Obama's Senate chief of staff and a senior campaign adviser, who also is White House-bound.

In her new role, Mastromonaco will execute elaborate protocols that have been in place for decades, and her immediate staff of about 35 will include a "diarist," responsible for recording every one of Obama's moves -- the telephone calls, the meals, the basketball games. Each step in the White House scheduling process, from request to approval, must be documented in writing. Decisions are made by committee -- a very large committee of administrative heavyweights from the national security and domestic policy offices, speechwriting, catering, the first lady's and vice president's shops, the Secret Service and so on. Advance teams involve casts of hundreds, swarming into each of the locales, here and abroad, that a president will visit.

The process is "very regimented, very bureaucratic," said former White House aide Bradley Patterson, author of "To Serve the President," about the machinery behind the man.

In the Bush White House, for instance, nine people -- including political boss Karl Rove when he was still on staff -- meet weekly to sift through some 1,000 requests and decide where the president should go. A confidential electronic calendar charts everything in the mix for the next 18 months to two years; wall boards in the scheduling office document flow charts for each day over the next four months. "There are no surprises!" said Patterson. "No one wants to be surprised."

"The flow of communications seems daunting for sure," said Mastromonaco, who has been debriefing current and former White House staffers, including Betty Currie, who worked for President Clinton. "We really had it down to a science in the campaign, and getting to know a load of new people and prove yourself once again is an exhausting thought."

Because she didn't travel with Obama or speak to reporters, Mastromonaco was the least-known member of the senior campaign team. But she became closer to the candidate personally, and played a more influential role in developing and executing campaign strategy, than did some of her more visible colleagues.

Her credits include all of Obama's high-profile appearances, from his announcement speech in Springfield, Ill., to the Berlin rally before 250,000 to the Denver convention speech and the election night celebration in Chicago's Grant Park. She choreographed Obama's 2006 book tour, his debate "camps" and the secret negotiations that led up to Sen. Joseph Biden Jr.'s selection as his running mate.

She's made her share of mistakes. Early on, Mastromonaco booked a private plane for the wrong day. Obama shrugged it off and flew commercial. Days of ridicule might have been avoided had she caught the faux presidential seal before it was unveiled at a June event. At the end of the Europe trip, a visit to Landstuhl Regional Medical Center in Germany was abruptly canceled after U.S. military officials argued that Obama would be visiting the hospital as a candidate, instead of as a senator.

But over two years, "she just hung the moon," said campaign manager David Plouffe. "Every time we had a high-wire act, Alyssa would come through." Her plans to get Obama into as many markets as possible between the South Carolina primary and Super Tuesday -- just 10 days -- were, said Plouffe, "a thing of beauty."

* * *

Her first memory of event planning is from nursery school. Her signature blend of extroverted insistence on organization and political savvy asserted itself when she threw an elaborate party for one of her teachers. She called a meeting with her fellow 4-year-olds and gave each of them an assignment: cupcakes, streamers, balloons.

"The teachers scolded me for organizing a rogue party!" Mastromonaco remembers. "But I had all bases covered."

The daughter of a business consultant and a high school teacher, she grew up in Rhinebeck, N.Y., and started in politics on the fringe, while she was studying French and Japanese at the University of Vermont. It was 1996, and Rep. Bernie Sanders, the frumpy and somewhat prickly socialist since turned senator, was seeking a fourth House term. He showed up at her dorm to campaign; she decided to intern for him.

"He would ask about my life, and talk to me about what was happening in Washington, D.C.," when she drove him to events or hung around the office, she said. "Even though I was just a sophomore in college, he treated me like I had a brain and something to contribute."

One of Mastromonaco's jobs was to call voters in the Northeast Kingdom, the most conservative part of the state. It wasn't an easy sell, but the small-town girl with a head full of Baudelaire found this all fascinating. "I became obsessed with Bernie Sanders and politics," she said.

She transferred to the University of Wisconsin and changed her major to political science, and in 2000 -- after a pleading letter and three interviews -- Mastromonaco persuaded Sen. John Kerry's Boston office to hire her as a $19,000-per-year staff assistant.

It was not a glamorous job, but it was revealing. She learned she could keep a secret when Kerry landed on Al Gore's vice presidential short list and Mastromonaco helped to see Kerry through the selection process, without feeling compelled to tell all her friends. And with her amazing memory and unflappable demeanor, she was a natural at logistics. Sending Kerry around the country to campaign for Gore, she found it thrilling to inform him, "This FedEx plane is going to pick you up in Miami and take you to Pittsburgh."

After Kerry's presidential campaign, Obama hired her to be his Senate scheduler, said Rouse, because the freshman senator sensed her political astuteness. Obama already had a high profile, and everyone wanted a piece of him. Mastromonaco's job was to turn down almost every request.

A year later, she became political director of Hopefund, Obama's political action committee, and dispatched both money and the senator to particular candidates for the 2006 congressional races. At every stop on the trail, Mastromonaco would line up a local official or two for her boss to meet -- just in case.

After that election, Obama started to think seriously about running for president, and Mastromonaco was part of the small group called together to walk him through the process. She created a mock three-month schedule to show Barack and Michelle Obama what a campaign would entail. When the senator decided to proceed, Mastromonaco was among his first hires. At first, Mastromonaco and Obama weren't an obvious match. She can be a bossy micromanager. She played flute growing up, not sports. And she carried the baggage of Kerry's losing campaign, with all of its leaks and infighting. "He's not D.C., and I seemed very D.C. to him," said Mastromonaco of Obama. "He would say, 'Why would you even want to do this job?' We didn't know each other at all. I had to convince him that I was a real person."

Their bond was forged when they started traveling together in 2006, and spent hours driving through congressional districts and to book-tour events. They would eat meals at Subway, stop for gas station snacks, and tangle over radio stations and the temperature (Obama likes the car warm). Eventually, Mastromonaco felt comfortable enough that she stopped carrying a Time magazine to disguise what she was really reading: Us Weekly, or Star, or some other celebrity rag. Soon they were flipping through the magazines together.

When her White House job became official last month, Obama issued an unusually effusive personal statement, describing Mastromonaco as a "talented and dynamic individual" with "diverse skills" who is "ready to work hard in service to the American people."

But starting Jan. 20, the formalities begin, and it's all fodder for the White House diarist.

"You always have to remind yourself, he's the president-elect," Mastromonaco said. "I used to call him Barack. He wants me to keep calling him Barack. But it doesn't feel right anymore."

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