the office

The Subtle Art of the Executive Assistant

New York Stock Exchange in 1966. Photo: Leonard Freed/Magnum Photos

One afternoon, I ran into Emily in the office kitchen. Emily was the executive assistant to the CEO of the company in downtown New York where we worked. Like all of the CEO’s assistants past and future, she was offensively overqualified for her position (in her case: double major at an Ivy League school, fluency in four languages).

It was 11:30 a.m. when I found her maneuvering a cake out of the refrigerator and onto a stand. There was a board meeting that day. Emily (a pseudonym) had somehow figured out that it was a key investor’s birthday — and that the investor followed a vegan, gluten-free diet and disliked chocolate. She had obtained a vanilla cake meeting the above requirements as well as a glass stand in the precise Pantone shade that was our company’s color, and she had coordinated with the office facilities staff to have the cake positioned at the end of the board’s private lunch buffet as a surprise.

The goodwill generated by this gesture would accrue to her boss, the CEO, which was Emily’s intention and, in fact, her job. “But how did you know to do all that?” I asked, once she’d gotten the cake on its pedestal. She erased a smear of errant frosting with a Q-tip.

“Oh, you know.”

Humility is another requirement of executive assistants. Inside that “you know” existed a process that Emily enacted a dozen times a day: locating an opportunity (birthday), considering angles of attack (wrapped gift? Personalized bottle of Champagne? Cake?), weighing risks. One of the risks here was that she hadn’t cleared the cake with our CEO in advance; she had calculated that bothering him with cake trivia was less desirable than risking disciplinary action if the investor hated the cake.

When I found Emily in the kitchen, it was exactly one hour before lunch. She had set a timer to remove the cake from the refrigerator so it would be an optimal temperature when served — firm enough to maintain its shape in case the investor wanted to Instagram it but not so cold that it would be unpalatable.

In these ways, an executive assistant occupies a peculiar place in the modern office. She is her boss’s social ghostwriter and clairvoyant, the composer of birthday cards to his wife, the culler of his email, the stocker of Tide pens and mouthwash and Advil. She knows which foods give the CEO gas. The role requires extreme intimacy paired with utter deference. It has less in common with the average 21st-century knowledge worker than with a domestic servant in Edwardian England (if a domestic servant had the power to destroy her boss’s life by leaking an email). The job used to be called “secretary” or “executive secretary.” Now, it has been nominally upgraded in many places to “chief of staff.”

It is fashionable among organizations like the one where I worked to promote the appearance of a flattened structure. “There’s no hierarchy here,” the CEO liked to say. In his eyes, this was true. Instead of having a corner office, he sat at an unguarded desk. Employees did not have to penetrate layers of doors and personnel to reach him; they could walk up and say hello. But, of course, nobody did. The trappings of prestige had been eliminated, but that just left employees to infer boundaries, and everyone erred on the side of caution.

Except Emily. Curiously, the bearer of this entry-level job was the only person in the company authorized to interfere with the CEO at any time and in any state. With his assistant, the CEO maintained a strange pantomime of helplessness — a manufacturing of the notion that without Emily, he wouldn’t know how to make a call or locate an email. Both parties knew that he could easily do these things and that it was simply not worth his time to do so. But in an age when job and identity are entwined, it’s painful for two people to acknowledge that one is more valuable than the other. So when Emily delivered his lunch in a meeting, he gave her a “What would I do without you?” look, and she lobbed back an “Oh, nonsense” look, and a form of dignity was maintained.

An executive assistant’s job, in other words, is to make herself irreplaceable. The problem is that this rules out any chance of career advancement. If the CEO can’t live without Emily, why would he ever promote her? A second paradox embedded in the job is that the skills required of an executive assistant — a strategic mind, iron discipline, a talent for empathy, and a knack for crisis mitigation — are identical to the skills of a capable CEO. Such talents can be directed at a birthday cake or a ten-year growth plan. It often occurred to me that if the CEO were to die in a tragic accident, Emily would be best qualified to replace him. I wonder if the thought ever crossed his mind.

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The Subtle Art of the Executive Assistant