Few figures in American politics have managed to capture the public’s imagination quite like Barack Obama. As the 44th President of the United States, he led the nation with a unique blend of charisma, intellect, and an approachable demeanor. However, what was it really like to work for him in the White House? Insights from former staffers paint a picture of a leader who was both demanding and deeply caring.
During his time in the White House, Obama lived with his family, including his wife Michelle, daughters Malia and Sasha, and mother-in-law Marian Robinson. Despite the privileges that came with being the First Family, Obama was not one to indulge in the royal treatment that some might expect. Stephen Rochon, who served as the director of the Executive Residence and White House Chief Usher, shared that the Obamas preferred a more laid-back approach. Unlike other presidential families who often relied on a constant stream of staff assistance, the Obamas valued their privacy and independence.
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This preference for a low-key lifestyle didn’t mean that Obama was laid back when it came to his work. In fact, he was known for his high expectations of his team. Former White House Press Secretary Jen Psaki recounted in her memoir, “Say More: Lessons from Work, the White House, and the World,” that Obama maintained a calm and cerebral demeanor. Unlike some leaders who might shout orders, Obama’s rare moments of raised voices were particularly impactful, leaving staffers feeling a sense of urgency to avoid mistakes. Psaki noted that his disappointed reaction to errors reminded her of her mother’s disapproval, which only heightened the seriousness of the situation.
Obama’s former staffers couldn’t have asked for a better boss
Despite the pressure, many staffers had nothing but praise for Obama. They acknowledged that while he was a tough boss, he was also the kind of leader who genuinely cared about their well-being. His approach to leadership extended beyond mere policy decisions; he offered life lessons that resonated with his team. Former Deputy Chief of Staff for Operations Alyssa Mastromonaco described Obama as a “cool boss” in her book, “Who Thought This Was a Good Idea?: And Other Questions You Should Have Answers to When You Work in the White House.” She recounted how he would take a personal interest in her life, even playing matchmaker by suggesting potential dates.
The personal touch didn’t stop there. When Mastromonaco’s beloved cat passed away, Obama reached out to console her. “I heard we lost Shrummie today,” he said, expressing his empathy and sharing that the mood on Air Force One was somber. His ability to connect on a personal level made a lasting impression on his staff.
Obama’s commitment to the health and well-being of his team was also notable. A fitness enthusiast himself, he encouraged his staff to prioritize their health. He was known to be supportive of team members stepping out of meetings to hit the gym, fostering a culture that valued wellness. In a lighthearted moment, he even offered to connect a senior adviser with his personal trainer when he noticed the adviser had gained a few pounds.
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Beyond the humor and camaraderie, Obama imparted wisdom that his staff carried with them long after their time in the White House. Pat Cunnane, a former senior writer and Deputy Director of Messaging, recalled one of Obama’s favorite sayings: “You’ll never have a better opportunity to do more good for more people than you do right now.” This mantra resonated deeply with his team, serving as a reminder of the impact they could make during their tenure.
In summary, Barack Obama’s leadership style was a unique blend of high expectations and genuine care. He created an environment where his staff felt valued and empowered, balancing the demands of the presidency with personal connections that left a lasting impression. As former staffers reflect on their time with him, it’s clear that Obama was not just a boss; he was a mentor and a friend who inspired those around him to strive for excellence while maintaining a sense of humanity.
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