Former White House Speechwriter Has A Problem With Michelle Obama Being A Demanding Boss


First Lady Michelle Obama has created a high-pressure environment and a few people who used to be on staff don’t like it. That’s one of the apparent messages from former White House speechwriter Reid Cherlin’s recent article on her called “The Worst Wing.”

It’s clear from his conversations with staffers that Obama is a perfectionist who demands high performance from her staff. “Former staffers describe a high-stress, high-stakes workplace,” he writes, “in which Mrs. Obama scrutinized the smallest facets of her schedule.” She conveyed that her time wasn’t to be wasted. “Mrs. Obama made it clear to her staff that…her time was a valuable asset and requests to use it would have to meet an exceptionally high bar,” he says. One ex-aide said the message conveyed about events was, “Don’t do it if it’s not going to be perfect.”

That certainly sounds stressful. One ex-aide told Cherlin that the situation “just made you super anxious.” But would the situation have been different if, say, they worked for the president? Or for a Senator? The nature of working in a high-stakes political environment is that you have to cope with a lot of intense demands.

Yet there’s something about Michelle Obama creating this environment that seems to grate at Cherlin.

Perhaps the problem is that people don’t like to work for demanding female bosses. No doubt her husband expects incredibly high performance from his staff and gets frustrated when his time is wasted. But the article hints at one potential problem for Michelle: a former employee told Cherlin that employees “don’t want to work for her; they want to be friends with her.”


This is a trap that ensnares many women in leadership roles. As sociologist Marianne Cooper writes, “decades of social science research…has repeatedly found that women face distinct social penalties for doing the very things that lead to success.” We stereotype women as warm, friendly, nurturing — but “if a woman acts assertively or competitively, if she pushes her team to perform, if she exhibits decisive and forceful leadership, she is deviating from the social script that dictates how she ‘should’ behave,” and that leads to a backlash. Americans prefer working for a male boss over a female one by 12 percentage points — although the good news is that a growing number say they don’t care. But the backlash doesn’t just come from male underlings. Two-thirds of women in a British survey said they preferred a male boss. Both men and women say they prefer a man to fill a senior executive role or to be president of the United States.

Another problem is that, it seems, she’s a perfectionist who doesn’t like to take risks or go off message. This may in part come from her time working as a corporate lawyer. One alum from her staff says, “[S]he’s a lawyer. She’s really disciplined. She cares about the details. She’s never going to wing it.” She has also always held herself to a high ideal. “She’s your ultimate straight-A student,” one former aide says, “she was used to being perfect.”

And it makes sense that Michelle Obama has had to hold herself to the highest standards and stay disciplined. Women and people of color have the odds stacked against them in the workplace, particularly in high-wage professions like the law, and Michelle Obama faces both sets of barriers. Black job applicants are half as likely as equally qualified whites to get callbacks or offers. In one experiment looking at women’s chances of getting hired for a math job, they were half as likely to get the offer based just on their gender. Nearly a third of women say they have experienced discrimination at work. It takes intense determination and peak performance to overcome those barriers as she has.

Michelle Obama also has to tackle these double standards in a role that is already rife with antiquated sexism. Cherlin acknowledges that “the position of first lady has become embarrassingly anachronistic,” filled with banquets and social engagements and representing an uncharted sea of how to take on an agenda with substance. In her book on the Obamas, Jodi Kantor writes that Obama “knew the history of first ladies — like Nancy Reagan and [Hillary] Clinton — who had been deemed meddlers, unelected figures who wielded unearned power.”

But like them, she came to the role with her own personal accomplishments and interests. Cherlin is clearly in the camp of those who were disappointed that she wasn’t able to transform the role to suit those accomplishments. He had hoped that her “political appeal and charisma would enable her to transform it into something that reflected the role of modern women as equal participants in the political process” — a daunting task given what has faced past first ladies who tried the same.


And even so, it’s hard to say that she has failed. Cherlin accuses her of “outlin[ing] a distinctly narrow vision,” but on her resume are Let’s Move, a campaign to tackle the problem of obesity among the country’s children, and Joining Forces, which helps military families and veterans. Next up is her new effort to tackle inequalities in our college system. While the article note that it has “so far fallen short of one of the strategic plan’s key recommendations — that it be supported with substance, like proposals for legislation or policy changes,” it has only been public since November. And as some have noted, like MSNBC’s Melissa Harris-Perry, simply being mom-in-chief is a radical act for a black woman, busting the Mammy stereotype.