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Ethan Bull 11 min read

How to Find the Right Executive Assistant

How to Find the Right Executive Assistant 

This article is adapted from The 29-Hour Work Day.

In the early 2000s, Ethan worked for one of the largest, most high-profile advertising agencies in the United States. Their offices were located in Manhattan and were run by a celebrity in the field. He had a brash personality—a “true New Yorker”—was opinionated and not afraid to yell. Consequently, at that time, many on his leadership team ruled their departments in a similar style.

Ethan entered the company as the assistant to the man leading the digital and direct/print production portion of the agency. He was a man who yelled—a lot! To say he was demanding would be an understatement. So perhaps it’s no surprise that, prior to Ethan’s arrival, he had gone through thirteen assistants in the previous twelve months.

That last line is not a series of typos—the man literally had thirteen assistants in twelve months. Yes, you could say he was a bit of a tyrant. However, in the end, Ethan got the last laugh; he stayed with the company longer than his principal did. You could also say that if Ethan’s principal had been a little pickier and taken the time to find the right EA for him from the beginning, he would not have spent so much time looking for others—time he could have spent on activities that would positively impact the company’s bottom line.

Granted, it can be difficult to find the right EA. Everyone looks almost too perfect on their resume. So, here are some key considerations to keep top of mind when recruiting an EA.

Look Beyond First Impressions

As with a resume, that first handshake and the first conversation you have may not give you an accurate portrayal of your candidate. Their speaking voice and the way they make eye contact and hold their posture during the initial interview will be done with utmost care to present to you the person you want to hire—not necessarily the person they really are.

Gruff people can pull off polished and charming for an interview. So, go beyond that first impression and ask questions aimed toward revealing what may be behind the veneer. 

1. How did they manage their previous principal's time? Can they give an example of when it was more tricky than usual?

2. What about an example from when they had to play the role fo gatekeeper? How did they deal with the senior leadership team wanting to see the executive without an appointment of checking with them first?

3. How did they handle a crisis or problematic situation? 

Listen to the answers and look for clues that tell you whether this person used EA superpowers to achieve the best results for everyone. And, if not, were the results they achieved accomplished with panache and confidence? Or with abrasive assertiveness? Based on their answers, you should ultimately ask yourself: is this the kind of person I want representing me and my company?

Something to keep in mind as you are interviewing is that a pause before answering is not a negative. EAs often perform so many functions and have been through so many different scenarios that they may need to stop and think about specific examples to pull from a vast array of experiences. 

So, instead of asking them, “What did you do at Company X?” instead ask, “Tell me what your responsibilities were when you first started.” Then, when they have answered that, ask them what their responsibilities were when they left (or are currently fulfilling). Compare and contrast the two, and you will be able to fill in the blanks for a full scope of their capabilities.

Additionally, pay attention to the way a candidate answers your questions. If you have to continue to pull a thread to get them to tell you their story in a succinct way, realize that is probably how they will interact with your clients and staff members. Such a communication style makes it difficult to create personal connections and partner with others.

Be Casual

We always suggest that principals try to have at least one interview that is more casual than an in-office meet-and-greet. Meeting over breakfast or lunch can be ideal because it will give the principal a better idea of what the person is really like. Your office, with a desk between you, will set up a psychological barrier that may prevent the candidate from giving you a full picture of who they are and what kind of character they possess. Whereas breakfast or lunch meetings tend to remove that barrier so you get a fuller, more real picture of them on which to base your hiring decisions.

At these meetings, consider their tone of voice—are they at ease having a general conversation? Do they easily make eye contact? How do they treat the staff at the restaurant? Are they pleasant to them? Does it seem as if this person will be congenial to work with? Being able to communicate clearly and effectively, to carry on a free-flowing conversation that doesn’t feel forced or stilted is so very important—especially in today’s world where so much interaction is done via phone or video conference.

In such a casual situation, you can also see how open someone is to criticism. A technique we use to check on that is to challenge people about how their resumes differ from their LinkedIn profile. Watching how they react to such a question in a relaxed atmosphere will reveal just how they will handle mistakes or corrections. 

Of course, the danger in such meetings is that the person may feel too comfortable and overshare personal information. That is yet another red flag. If they do not have the discretion to maintain a sense of privacy and confidentiality with their personal business, then you know they will not have it to maintain yours.

Your Gut Will Know

Often, you’ll know you have found the right EA because you will feel it in your gut. There have been times when we have found assistants that seemed perfect on paper—they had the skills, they had the experience, but our gut told us something was off. 

Every time we ignored our gut because a candidate’s on-paper information was just so very good, we regretted it. So listen to your gut. If your first instinct is to say “yes,” then it is probably right. Likewise, listen if your gut tells you “no.” In the long run, you will save time and aggravation if you have the wherewithal to sit and touch base with your instincts—and follow through on what they say. 

It’s often better to take your time when hiring an EA. A sense of urgency may cause you to discount any potential negatives in a candidate that could wind up causing you to let them go in just a couple of months and start the hunt anew (as with Ethan’s principal, who had to go through the search thirteen times). 

As Dr. Stephen Covey says, “What is important is seldom urgent, and what is urgent is seldom important.” It is more important you find the right person than it is that you find the first one to fill a vacancy.

For more advice on finding the right EA, you can find The 29-Hour Work Day on Amazon.

Ethan Bull is a co-founder of ProAssisting, a next-generation remote executive assistance firm for business owners and C-suite executives. With a background in hospitality and expertise in the EA space, Ethan has held a variety of senior positions, including Director of Administrative Services and senior EA to the president and CEO at Rochester Regional Health.

Stephanie Bull is ProAssisting’s co-founder and the former EA for J. Crew’s CEO and the CEOs of two multibillion-dollar hedge funds. Before developing ProAssisting, Stephanie proved herself an expert in the field and a vital addition to the C-suite by fulfilling a variety of roles, including chief of staff, estate manager, and investment liaison.

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Ethan Bull

Co-Founder of ProAssisting

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