You may have never heard her name, but Alyssa Mastromonaco was one of the most important people in the Obama White House. She joined then-Senator Obama’s campaign in 2004, after working for John Kerry on and off for four years, and followed him from Congress to the White House for two terms. She spent two years as assistant to Obama and as director of scheduling and advance, and then became deputy chief of staff for operations at the White House from 2011 to 2014. Without her, very few things would have gotten done.
Mastromonaco’s new memoir, Who Thought This Was a Good Idea? (out today), details her life — from bagging groceries in high school in Rhinebeck, New York, to making sure the slogan “Change You Can Believe In” was painted in the correct typeface on a Boeing 757 for Obama’s campaign travels. She is also the hero responsible for the tampon dispensers in the West Wing women’s bathrooms — they didn’t exist before 2004. The women Mastromonaco worked with garnered considerable media attention last year when they shared their strategy of “amplification”: if one woman spoke up at a meeting, another would repeat her point, and make sure to say her name in order to give credit where credit was due.
Today, Mastromonaco is the president of global communications at A&E Television Networks, but she and Obama are still in touch. Obama apparently requested a copy of her book, and read through “at least part of it” on a trip back from Asia. (His review? “Not bad, quite funny.”) On the day of the book’s release, Mastromonaco spoke on the phone with the Cut about what it was like to work with Obama and what lessons she took from her years at the White House.
Wanna get into politics? Don’t get a big head.
“It doesn’t really matter where you start off in your career — instead, it’s all about cultivating your interests. If you’re in high school, volunteer for a campaign. Work for a state-level candidate. I felt lucky because when I started interning in politics, I had a real worm’s-eye view. I didn’t glamorize what I was going to do. I knew I was going to be answering the phones, cutting clips (a thing that doesn’t even exist anymore). I never had illusions of my own grandeur, and people promoted me for it. I was always mission focused, which is super important. Work for people you believe in, look for organizations that you feel passionate about. I’m out of politics now but I’m freaking out about it. I still try to be super active, as much as I can.”
Work for someone you believe in — but remember that you are not the star.
“People always ask me about my job working for Obama, how did you do it? The honest answer is that I really only worked for people who I believed in. If you win or lose, if you become president or not, you haven’t really lost. I believed in Obama so much, and I never thought he was going to run for president! What he said he was going to do, he tried in every possible way to do. I can’t remember if it was James Baker or Rahm Emanuel who said it, but they said the most important word in the chief of staff title is ‘staff.’ Nobody thought that they were a principle unto their own right. You didn’t go work for him because you thought he was your vehicle to the West Wing. The people who were there, were there win or lose — though, of course it’s nice to win. He was the kind of president that he told us he could be.”
Sometimes you need to tell the president No.
“Obama hated having to tell people no. He’d say to me, ‘Tell them we’ll figure it out,’ and I’d be like, ‘Right but we can’t, because you’re in Hawaii.’ Telling the president no wasn’t easy, but the only way to do it was if you had a lot of facts and reasons. ‘What do you mean I can’t do that?’ he’d say. ‘Well you can’t move that because of this, this, and this.’ The flip side of the coin was that he also hated to keep people waiting. If he’s not on time for something, it is purely because he has been overtaken by events. If we were running over in a meeting and we had constituency groups visiting from Illinois, he would try very hard to be prompt. ‘They came all the way from Illinois!’ I’ve always hated being late, too. Even now, I’m the worst person you could ever have to do a book tour. ‘Uh, you guys, I just MapQuested the schedule and your drive time is wrong.’ I cannot be late.”
Be yourself, but know your audience.
“The person who I am right now is basically who I was in the West Wing. The only time I calibrated a bit was when I would deal with the White House military office. They knew the real me by the end, but I was a 34-year old woman who didn’t have a military background. I wanted them to know that I deeply respected them and that I wasn’t some Sweet Valley twit. I’m not saying it’s right to be seen that way, but it was very clear that I was political, I wasn’t military. It didn’t matter. I wanted to show them respect.”
Never leave the house without these two things (as well as a tampon — they are few and far between in the White House):
“I always had those little pads that can get deodorant off your clothes, and Silver Linings, which are these gel inserts that cool off my hot feet. My feet always got really hot, so I’d take my shoes off most of the time. Once, I was sitting in my office and I walked over to Dan Pfeiffer to ask him a question, and the president walked by with a foreign official. He didn’t even say anything, he just shook his head at me.”
You don’t always have to be in the room.
“Whenever anyone asks me about the day Osama bin Laden was killed, I’m completely honest about where I was: I was on my couch, eating Chinese food. I saw a breaking-news alert from CNN that Barack Obama was going to be giving a statement from the East Room. I emailed some people. ‘What’s going on? What are we doing?’ and everyone was like, I don’t know. We literally found out from breaking news on CNN. The people who were in that room needed to be in that room. Obama didn’t treat things like inner circles of importance: That was a national-security operation, so that’s who was there.
That’s why it’s crazy to see Donald Trump bring all these people to travel with him. Who is watching the Oval Office? They also use all the rooms in the White House arbitrarily. When Obama gave a statement in the East Room, you knew it was a big deal. America knew it was a big deal. If it was a Rose Garden statement, it was a big deal. With Trump, it’s interesting because they believe all protocol is bad, so you can’t ever tell what’s going happen.”
Bringing more people in to solve a problem does not guarantee a fix.
“When I worked for the Kerry campaign, I think that the biggest thing that I learned was the more people that you throw at a problem doesn’t mean you have a higher likelihood of solving it. Chances are that there is something else that you should be looking at. Being egalitarian was David Plouffe’s thing. Hierarchies can happen on campaigns, but with Plouffe and Obama, they were like, no, actually, you need to work together to produce the best product with the amount of people that we have. More people doesn’t mean more success.”
There will be some extremely difficult days.
“I didn’t put it in the book, but hands down, the day of the Newtown shooting was the hardest day of my job. The one thing that I felt passionate about in writing the book is that I only wanted to tell the stories that I really considered mine. On days like that, with a 24-hour news cycle, you wish everyone would take a beat. The first report that we got was that there might have been a mall shooting in Connecticut. The story evolved to what had really happened in 45 minutes to an hour. That’s the time when you realize how important your job is.
That’s why I wish that Donald could demonstrate more compassion. Something like this will happen on his watch, something that requires him to be the consoler-in-chief. People need to believe that that depth and sincerity is there. On Saturday morning after the shooting, I told Barack, ‘I really think you need to go to the memorial service on Sunday.’ That’s a brutal thing for any person to have to do, let alone someone with all eyes on him. From the time we found out what happened, we were synced up to the FBI and DOS and the governor and mayor’s offices. I immediately went and worked for the governor’s office in Connecticut. ‘What can we do, what do you need from us?’ That was one thing that Obama always really cared about: How can we help the local officials on the ground?”
The transition out of politics can be a difficult one.
“It wasn’t really politics that was hard to transition out of, it was knowing that I had to prove myself all over again when I started in a new industry. I worked with Jon Favreau for 12 years. I never had to be the new person. I was good. When I got to Vice, though, I was new. And you know what? Millennials are tough. Millennials don’t care that you worked at the White House, that you had a long career in politics. The only time anyone cared was when I told them I had worked for Bernie Sanders at one point in my career. Then all of a sudden, I had a halo over my head.”