How To Succeed As An Executive Assistant

photo by Steve Wilson

Everyone knows good help is hard to find. If you are an executive searching for a top-flight assistant - or even the other way around - it helps to know what you are looking for.

A friend of mine recently interviewed for a position as executive assistant to a CEO, and since I also happen to be the head of a company, she turned to me for some insight. She especially wanted to know what I consider to be the five most important attributes of an outstanding assistant.

I had to stop to gather my thoughts. Although I am my company’s CEO, I do not have an executive assistant who goes by that title. However, several members of our firm’s administrative staff perform those functions for me within the scope of their other duties. Moreover, a number of our firm’s clients have been CEOs and other top-level executives, so I have worked closely with EAs for many years. (For clarity, note that throughout this blog post I use “EA” to refer to executive assistants, though elsewhere on our website it generally refers to the Internal Revenue Service’s “Enrolled Agent” credential.)

Executive assistants, like administrative assistants generally, share some traits with the secretaries who were their historical predecessors. Yet the position looks different today. Yes, some EAs do field their boss’ phone calls or manage their calendars, but they may also attend meetings or negotiations, analyze business documents, prepare research reports and supervise more junior staff. Each executive will need a slightly different skill set from an assistant, depending on the industry, the company and the executive’s personal work style. Although the precise duties vary, the best assistants will typically display many of the same qualities.

Some of the EAs with whom I have worked have been remarkably skilled. Fans of USA Network’s drama “Suits” will recognize Donna in many of the characteristics I discuss, and not without reason. I see a lot of Donna in many of the EAs I know, minus the slinky designer clothes, questionable office banter and entangling personal relationships that are much more common on TV dramas than in real life.

So which five qualities are at the top of my list for an EA who is destined to be a star?

1. Loyalty. An outstanding assistant must be committed to the success of the enterprise as a whole, and to the executive’s efforts to guide it. The best EAs will not hesitate to give their boss an honest opinion, whether to agree or disagree, but they will never criticize or undermine their bosses behind their backs.

2. Discretion. A high-level EA will inevitably have access to highly sensitive information, including information about the company itself, its clients or customers, and fellow employees. The assistant’s boss must trust that the EA will never share or use this information inappropriately.

3. Judgment. An executive assistant is the gatekeeper for much of the information flowing toward his or her boss. He or she must discern which items require immediate attention, which can wait and which should be redirected to someone else’s desk. Perhaps most important, excellent EAs know when to ask their bosses for guidance. Some of this judgment comes with experience, but some is simply a cultivated sense of how to properly evaluate the boss’ priorities. A smart EA will also know when something is worth handling differently than usual.

4. Initiative. To maximize both their assistant’s efficiency and their own, accomplished executives want to drop as many problems as possible into the assistant’s lap. Assistants must be prepared to tackle a wide array of challenges, from regular tasks to rare and complex projects they have never encountered before. By the way, bosses also appreciate assistants who, when alerting them to a problem, simultaneously offer a potential solution.

5. Accuracy. Top executives usually care a lot about details, but their jobs do not allow the time to get deep into the weeds. They rely on others to present information clearly, concisely and - above all - accurately. After all, you can’t make good decisions on bad information. The strongest EAs are masters of detail.

You will notice I did not include items like “organization,” “effective communication” or “time management.” That is because those sorts of skills are basic requirements, not distinguishing traits of a star performer. A disorganized assistant to a top-level executive does not stay in that job very long.

Today’s executive assistant need not type letters or learn stenography. I think of the position in much the way Eleanor Roosevelt is sometimes portrayed in her working relationship with her husband - someone whose loyalty is unquestioned, ready to act as eyes, ears and troubleshooter.

The best executive assistants make themselves equally indispensable. They also have one more characteristic I have not mentioned: They are often choosy about who they work for. If you are lucky enough to find one of these high-powered assistants, you need to know how to get the most out of that individual. Or else you should ask your new assistant to show you how it’s done.