The Room Where It Happens: 6 Revealing Books by Presidential Staffers

May 15 2019
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We all want to know what it’s like to work in the White House and to be in The Room Where It Happens. We don’t all want to endure the grueling campaigns, partisan battles, and policy debates that go with that territory, however. Conveniently, that’s where political memoirs come in. They’re an easy way to satisfy our curiosity about how our democracy works without ever having to set foot in Washington, D.C. And whereas elected officials can offer one side of the story, their staffers see things from a whole other perspective. From them we can get the inside scoop about everyday life in the West Wing. With that in mind, here are six books by former presidential staffers sure to please any armchair politico.

West Winging It
by Pat Cunnane

Everyone starts somewhere, and for Pat Cunnane, that meant a warehouse job he couldn’t wait to escape. So how exactly did he end up becoming President Obama’s Senior Writer and Deputy Director of Messaging? Cunnane chronicles this extraordinary career path in his memoir, WEST WINGING IT, a book aptly described as a mix between The West Wing and The Office that highlights the mundane and extraordinary moments of the administration alike. Plus, woven throughout his story are fascinating memories of his boss outside the public eye that only a senior staffer could tell.

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West Winging It
Pat Cunnane

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Yes We (Still) Can
by Dan Pfeiffer

Best known these days as a cohost of the podcast juggernaut Pod Save America, Dan Pfeiffer rose to prominence as President Obama’s White House Communications Director and then his Senior Adviser for Strategy and Communications. Before that, though, Pfeiffer was just an idealistic young political operative hopping from campaign to campaign, soaking up all the experience he could along the way. He reminisces about it all in his compelling memoir, which also offers a thrilling firsthand account of Obama’s 2008 presidential run, thoughts on what happened in 2016, and suggestions for Democrats in future elections.

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Yes We (Still) Can
Dan Pfeiffer

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MENTIONED IN:

The Room Where It Happens: 6 Revealing Books by Presidential Staffers

By Heather Waters | May 15, 2019

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Treating People Well
by Lea Berman and Jeremy Bernard

Who better to write a social etiquette guide than two former White House Social Secretaries?! Lea Berman and Jeremy Bernard—who served in the George W. Bush and Barack Obama administrations, respectively—bring their extensive knowledge of office manners to bear in this practical how-to. Full of personal anecdotes and life lessons from their time serving the president and navigating D.C. politics, the book dispenses tried-and-true advice that can help you succeed in any social situation, whether you’re struggling to get along with coworkers or need pointers on how to make friends in a room full of strangers.

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Treating People Well
Lea Berman and Jeremy Bernard

Two White House Social Secretaries offer “an essential guide for getting along and getting ahead in our world today…by treating others with civility and respect. Full of life lessons that are both timely and timeless, this is a book that will be devoured, bookmarked, and read over and over again” (John McCain, United States Senator).

Former White House social secretaries Lea Berman, who worked for Laura and George Bush, and Jeremy Bernard, who worked for Michelle and Barack Obama, have learned valuable lessons about how to work with people from different walks of life. In Treating People Well, they share tips and advice from their own moments with celebrities, foreign leaders, and that most unpredictable of animals—the American politician.

Valuable “guidance for finding success in both personal and professional relationships and navigating social settings with grace” (BookPage), this is not a book about old school etiquette. Berman and Bernard explain the things we all want to know, like how to walk into a roomful of strangers and make friends, what to do about a colleague who makes you dread work each day, and how to navigate the sometimes-treacherous waters of social media.

Weaving “practical guidance into entertaining behind-the-scenes moments…their unique and rewarding insider’s view” (Publishers Weekly) provides tantalizing insights into the character of the first ladies and presidents they served, proving that social skills are learned behavior that anyone can acquire. Ultimately, “this warm and gracious little book treats readers well, entertaining them with stories of close calls, ruffled feathers, and comic misunderstandings as the White House each day attempts to carry through its social life” (The Wall Street Journal).

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MENTIONED IN:

The Room Where It Happens: 6 Revealing Books by Presidential Staffers

By Heather Waters | May 15, 2019

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Who Thought This Was a Good Idea?
by Alyssa Mastromonaco

Imagine a political memoir written by Mindy Kaling and you’ll have a pretty good picture of how relatable and entertaining it is to read Alyssa Mastromonaco’s account of working at the White House as Deputy Chief of Staff for Operations... What, you need more incentive to check this one out? Okay, okay: It should also be said that Mastromonaco—who’s also an alum of the Obama administration and member of the Pod Save America podcast family—shares memorable anecdotes about everything from meeting the queen of England at Buckingham Palace, to crusading for feminine hygiene product dispensers in the West Wing, to coordinating Hurricane Sandy disaster relief.

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Who Thought This Was a Good Idea?
Alyssa Mastromonaco

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MENTIONED IN:

The Room Where It Happens: 6 Revealing Books by Presidential Staffers

By Heather Waters | May 15, 2019

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Madam President
by Nicolle Wallace

Another former White House Communications Director, Nicole Wallace skipped releasing a memoir in favor of writing a series of thrillers with a political bent influenced by her time in the George W. Bush administration. In her novel MADAM PRESIDENT, the MSNBC host spins a yarn about a reality in which the 45th president of the United States is a woman named Charlotte Kramer who has given the press permission to film a day-in-the-life documentary about her administration. Unfortunately, that very day, the country is attacked, and she and her staff must rise to the occasion even as they manage personal and professional secrets that could have a profound impact on everything and everyone they care about.

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Madam President
Nicolle Wallace

For fans of “Scandal”

Charlotte Kramer, the 45th President of the United States, has all the zeal, exploit, and secrets of “Scandal's” Olivia Pope. On the very day a network news is invited to document a day the life of President Kramer, five major attacks are leveled on US soil. Will the president’s secrets remain hidden in the face of the country’s possible downfall?

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You Can't Be Serious
by Kal Penn

Kal Penn has been on my radar since I was a teenager, when he appeared in movies like Harold and Kumar Go to White Castle and Van Wilder. If I’m being honest, though, it wasn’t until he joined the Obama administration as Principal Associate Director in the White House Office of Public Engagement that I considered myself a fan. In his memoir, You Can’t Be Serious, the actor-turned-political-staffer writes about how he achieved career success in two such different fields—and a few others, besides. Whether you come to it for insights into Washington, D.C. or Hollywood, or just out of curiosity about a man who’s done a lot of aspirational things in his life, this book’s sure to be pure entertainment.

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You Can't Be Serious
Kal Penn

In this refreshingly candid memoir, Kal Penn recounts why he rejected the advice of his aunties and guidance counselors and, instead of becoming a doctor or “something practical,” embarked on a surprising journey that has included acting, writing, working as a farmhand, teaching Ivy League University courses, and smoking fake weed with a fake President of the United States, before serving the country and advising a real one.

You Can’t Be Serious is a series of funny, consequential, awkward, and ridiculous stories from Kal’s idiosyncratic life. It’s about being the grandson of Gandhian freedom fighters, and the son of immigrant parents: people who came to this country with very little and went very far—and whose vision of the American dream probably never included their son sliding off an oiled-up naked woman in a raunchy Ryan Reynolds movie…or getting a phone call from Air Force One as Kal flew with the country’s first Black president.

With intelligence, humor, and charm on every page, Kal reflects on the most exasperating and rewarding moments from his journey so far. He pulls back the curtain on the nuances of opportunity and racism in the entertainment industry and recounts how he built allies, found encouragement, and dealt with early reminders that he might never fit in. And of course, he reveals how, after a decade and a half of fighting for and enjoying successes in Hollywood, he made the terrifying but rewarding decision to take a sabbatical from a fulfilling acting career for an opportunity to serve his country as a White House aide.

Above all, You Can’t Be Serious shows that everyone can have more than one life story. Kal demonstrates by example that no matter who you are and where you come from, you have many more choices than those presented to you. It’s a story about struggle, triumph, and learning how to keep your head up. And okay, yes, it’s also about how he accidentally (and very stupidly) accepted an invitation to take the entire White House Office of Public Engagement to a strip club—because, let’s be honest, that’s the kind of stuff you really want to hear about.

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MENTIONED IN:

The Room Where It Happens: 6 Revealing Books by Presidential Staffers

By Heather Waters | May 15, 2019

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