How to Hire a Great Executive Assistant

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Written By 33Vincent

Truly world-class Executive Assistants are rare. Many initially think that Executive Assistants simply take over smaller administrative tasks like ordering supplies or scheduling meetings. While that’s true, a great Executive Assistant is much more like a partner and gatekeeper to their senior manager, rather than simply a task taker. They manage their executives’ day-to-day with ease and accuracy while also elevating their work to the next level—all while making their boss look great. It’s easy to find an assistant, but hiring a truly great Executive Assistant is hard.

Luckily 33Vincent is here to help! We’ve sifted through thousands of applications, sample projects, references, and trial periods in our pursuit of truly exceptional Executive Assistant talent. Even after all of that, we still only end up placing around 1% of our candidates!

Today we’re going to share some of our expertise so you can learn how to find and hire an Executive Assistant that is truly exceptional yourself.


How to Find an Executive Assistant

1. Evaluate Your Organizational Needs and Cultural Fit

No two Executive Assistant positions are alike. Some organizations need specialized skills from their EAs, while others may require a more specific cultural fit. It’s not uncommon to need an Executive Assistant that has a certain number of years in logistics or CRM support. Similarly, we’ve found that company culture can also make a big difference in desired traits. The needs of a nimble, fast-changing startup are often not the same as a large, established corporation. You should start your search for your world-class Executive Assistant by deciding which skills, traits, and talents would be best suited to your organization.

2. Create a Candidate Profile that Highlights Core Competencies and Qualifications

Once you’ve got an idea of the types of skills and background you’re looking for, create an “ideal” candidate profile. In later steps, we’ll use this profile to quickly and efficiently rank your candidates’ fit with your organization, so don’t hold back. List out all the competencies and qualifications of your dream assistant. It also helps to rank these from most to least important, which will help you narrow the field later.

3. Create a Compelling Executive Assistant Job Description

Next, you’ll need to create a compelling job description so your position stands out against the hundreds of others that your dream Executive Assistant is sorting through. Be sure to keep in mind steps one and two when creating your job description, so right away you can begin appealing to the right candidates. You don’t want to present your organization as difficult, but you shouldn’t sugarcoat the tougher parts of the job either. Here you want to be as straightforward as possible while still being your own best cheerleader. The goal is to get your candidates excited about applying, while still providing them with a clear picture of what the role will entail.

Here’s an excerpt of our Executive Assistant job description, which has helped us find high-caliber EAs for years:

  • Does an organized inbox make your heart skip a beat? Does a color-coded calendar make you grin from ear to ear? You may be in the right place. Matched with a high-caliber Executive, your role is coordinating chaos: your client’s gatekeeper, sounding board, cheerleader, detective, and you aren’t afraid to provide recommendations and accountability. You speak up in order to make your clients' work better.

4. Create a Distinctive Job Posting, Utilizing Your Network and Outside Job Boards

Now it’s time to take the job description you just crafted, and create a job posting that will attract great candidates. Front-load the posting with information about your organization so the applicants can get a clear picture of who they’re applying to—just like your job description above will give your Executive Assistants a clear idea of what they’re applying for.

Always be sure to light up your own social channels, encouraging your colleagues to share your job postings and asking your networked peers if they have any good recommendations. If they’ve worked extensively with an Executive Assistant, chances are they will. In fact, we at 33Vincent initially grew almost exclusively through happy clients ourselves!

Finally, be sure to post on outside job boards. There are many to choose from, and we find it’s most helpful to post our Executive Assistant positions in several different places. However, sorting through numerous job posting sites and downloading applications is no easy task. We recommend you request your potential Executive Assistants to apply via a link inside the job posting or to send their materials to a specific email instead of using the defaults provided on job sites. This will allow you to instantly weed out those without the attention to detail that world-class Executive Assistants must have, and also save you a lot of time hopping from site to site in the process.

5. Narrow Down the Candidates

As the applications begin to roll in, it’s important to notify candidates that their application has been received. Even an automated notification has been shown to keep jobs at the top of applicants’ minds, and you’ll need to be top-of-mind for the next step! After a couple weeks (or perhaps a month depending on how many places you posted your job) you should have a number of applicants you can now begin to whittle down.

Start by ranking your Executive Assistant candidates based on the dream profile you created in step 2 above. Once you’re confident you have your candidates ranked from top to bottom, send the bottom 50% a notice that they were not chosen for the position.

6. Perform a Skills Test and Phone Interview Screen

Now, perform a skills test with the top 50% of candidates. At 33Vincent, this takes the form of a sample project. Be sure to choose a test that is comprehensive and utilizes the top 4-7 skills or qualifications you’re interested in seeing from the candidates.

After that, you can narrow down even further based on how those skill tests turn out. Divide your candidate pool in two again, and you should be left with the top 25% of candidates. Be sure to go back and turn off your original job postings if you feel like you already have enough candidates as well!

From here, it’s on to the first phone screen.

This serves several purposes. First, you want to make sure the candidate actually knows what they’ve demonstrated in the skills tests. It’s easy in today’s information age to simply Google the answers and respond in kind. Be sure to ask what, how, and why questions in response to their answers to really get a grasp of what they’re saying—and to ensure they have that grasp as well!

Besides testing their actual knowledge, the phone screen is also a great view into their personal communication style and how they respond to pressure as well. Look for candidates that have personal goals and are lifelong learners. Answers here are a good glimpse of whether or not they’ll fit with the company culture. Make sure to screen out those who seem like they’re simply regurgitating the original job post.

And always, always, be sure to take notes on their answers! Good notes will allow you to craft personal questions, which is extremely important in the final interview.

7. Draft Insightful Interview Questions and Conduct Interviews

From here, it’s on to the in-person or video interviews. It’s important to start off the interview by setting a good tone: be enthusiastic with your candidates, and let them know you're excited to interview them! Match their level of enthusiasm, mirror their social gestures, and repeat back things they say when appropriate. This will help them settle in, and calm candidates give more accurate answers.

Start off by asking the candidate to walk you through their last 10 years or so of job experience: what their roles were like, what they learned, where they excelled, and most importantly, where they failed.

Everyone asks the question, “What are your most important strengths and weaknesses?” and every candidate prepares for them. The best way to steer away from those cookie-cutter answers is to work those questions in discussing their previous job history. It’s also important to remember some strengths and weaknesses can change depending on what their position at the time was.

Of course, some weaknesses will be red flags (like those that conflict with the top 4-7 skills you're looking for), but the primary purpose of the strengths and weaknesses questions are to gauge the candidates’ honesty. A truly great Executive Assistant will know exactly what their weaknesses are, and will have developed ways of dealing with them.

Here are some example questions during each job in their history:

  • What were the specific duties you were hired to complete? How did you complete them?
    The object here is to understand their initial goals and if they completed them. Keep your ears open for insight into what their performance may have been like at that past position.

  • How did your work in that position affect your executive's productivity and focus?
    A great Executive Assistant will have a good understanding of exactly how their work acted to benefit their previous executives!

  • What achievements are you most proud of from that role?
    Here you want to listen for the experience that backs up the skills they claim in their resume.

  • What are some challenges you’ve run into with your previous Executives? How did you navigate those challenges?
    Everyone runs into challenges now and again. However, how an Executive Assistant overcomes those obstacles is key to understanding if they’re a good EA—or truly great!

  • What were the low points during that job?
    Every job has its low points, and everyone makes mistakes. If they can’t tell you any low points, keep pushing until they give you something. Ask for their largest mistake, duties they didn’t like, things they might have done differently, or what the culture was like and how they felt about it.

  • Why did you leave said job?
    Did they leave that job in search of a raise? Were they recruited? Were they fired? How did their boss react? Get a feel for how they have planned out their career, and whether or not they were valued by their bosses before they left.

As you continue through the job history, take note of self-improvement. An ideal candidate should learn and grow with each job experience. A negative experience with an employer here and there shouldn’t automatically disqualify someone who’s gotten this far—in fact, being honest about negative experiences is a plus—but keep an eye out for continued clashes throughout various jobs, as that may signal an issue.

Finally, plan out more in-depth follow-up questions based on the notes you’ve taken from the phone interview. These questions might cover specific skills or qualifications, or “What if X happens” type questions. You can also try to follow up on things that might have caught your attention during their job history as well. When in doubt, probe deeper.

Always keep in mind that people will usually volunteer more information if you simply remain quiet. If you want to know more about an event or a skill, simply don’t say anything after they’ve finished.

8. Conduct a Full Reference and Background Check

After you’ve weeded out even more candidates based on the in-person interview, you should be left with a few candidates, including the one that will likely be your rockstar Executive Assistant! Now is the time to follow up with those references.

In addition to asking about their general performance, be sure to ask questions about specific events or instances the candidate mentioned as well. Keep in mind that it might have been a while since they worked for their references, but they should still remember some of the highlights. Listen for any inconsistencies, as that may be a sign the candidate was not being totally forthright about their experiences.

9. Finally Make Your Offer and Negotiate Salary

After all the references and background checks have been completed, it’s now time to select and hire your final candidate! Go back to the very beginning of this list, and compare your candidates side by side. Choose which one has the best skills and qualifications for your organization.

Sometimes, it’ll be very hard to decide between two or three candidates, and an additional interview might be required. In more rare instances, the in-person interview and reference check might cast doubt on your candidates. Don’t lose hope! The right candidate is out there, it just might take some work to find them.

When negotiating salaries, it also helps to start off with an acceptable range in mind. Make a note of your minimum and maximum offer before you begin.

By following all of these steps, you’ll be able to hire a great Executive Assistant!


Don’t Have the Time for All Those Steps?

A great Executive Assistant is an invaluable asset. If you need a world-class Executive Assistant ASAP, or simply
don’t have the extra time to devote to finding the perfect candidate, try our Executive Assistant Search today!

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