How to Interview an Executive Assistant (And What It Takes to Find Top Talent)

If you were to ask a hiring manager or recruiter, “What’s the most important step in evaluating executive assistant candidates?”, most of them would say the interview. 

And in the traditional process of posting a job description, reviewing applicant resumes, and interviewing a handful of the most promising candidates—the interview is the most revealing step of the hiring process. 

However, based on our experience assessing tens of thousands of executive assistant candidates, relying solely on resumes and interviews when hiring an executive assistant (EA) often leads to poor outcomes. Many people with an adequate or even impressive resume can speak well in an interview but not end up working out well once they’re on the job.

So while interviews are important, they’re not sufficient for ensuring you make a good hire because they’re based on hypothetical discussion—not concrete evidence someone will perform well in practice. 

Among other key steps like performing thorough reference checks, you also need to see samples of candidates’ actual work in order to be certain they can do the types of tasks you want them to do (more on this later).

Whether you’re a hiring manager preparing to interview EA candidates for an executive at your company, or an executive planning to interview and hire an EA on your own, this article will provide you with key insights on how to properly interview EAs. 

We’ll cover:

• The key qualities to look for when assessing and interviewing EA candidates
• Best practices for interviewing executive assistants
• Examples of structured interview questions to ask candidates
• How to execute work sample tests and reference checks to more thoroughly vet candidates
• The hiring methodology we’ve built for finding top-level EA talent (and how our executive assistant service works)

Note: Our unique hiring methodology enables us to find world-class executive assistants for our clients. We hire roughly 1 out of every 1,000 candidates. If you’ve been wanting an assistant but haven’t had the time to hire one, click here to get started. You can try an assistant for a month or two and see how you like it. For testimonials from our clients, check out our homepage.

Before the Interview: Understanding the Key Qualities to Evaluate in Executive Assistant Candidates

Executives and hiring managers generally have an intuitive sense of the qualities and skills they’d like their EA to have. For example, they want someone with soft skills such as: 

• Communication skills
• Organizational skills
• Trustworthiness to handle confidential information
• Ability to work as a team member

And they also want someone with certain technical skills such as:

• Mastery of scheduling and email management
• Competency with learning software programs
• General computer skills

These are all valid qualities and skills to look for. However, people who hire executive assistants also tend to pay attention to other variables that aren’t actually that useful and don’t predict success in an assistant role. For example:

• Prior years of experience in an administrative assistant or executive assistant position. (Because EAs require generalist skill sets, it’s unnecessary to rule out people who don’t have past experience as an assistant. There are many individuals without past assistant experience who have the necessary qualities and skills to excel in the role. In fact, we often find the best candidates don’t have past experience as an assistant.)
• Whether they’ve held a previous position at a blue chip company or brand name. (Just because someone has worked at a known company doesn’t tell you anything about whether they have the right qualities for being a top EA.)
• Whether they went to a good school (Same as above. Just because someone went to a good school doesn’t mean they have the necessary qualities and abilities that make a great assistant.)

Over the past 4 years running our remote executive assistant service, we’ve learned that the key qualities that predict success in an executive assistant role are:

1. Problem-Solving Ability: How smart are they? Can they figure things out in new and complex situations? 
2. Key Character and Behavioral Traits: Are they highly motivated, resilient, organized, detail-oriented, etc.?
3. Communication Ability: How well do they write and communicate? Can they communicate on your behalf or alongside you with key stakeholders (executive team members, board members, investors, etc.)? 
4. Tech-Savviness: How comfortable are they with learning new technologies and software? How quickly can they pick up and learn the programs that modern companies use to run their businesses? (e.g. Notion, Asana, Superhuman, Calendly, Excel, Zoom, etc.)

If you can design your hiring process to rigorously vet candidates based on these qualities and abilities, you can find top talent who will excel as your EA (and in some cases be absolutely transformative for you and your business). 

The interview process, which we’ll discuss next, is one key aspect of this vetting process.

Best Practices for Interviewing Executive Assistants

When creating your executive assistant interviewing plan, it’s important to create two different types of questions:

1. Structured Questions: A strategic set of questions that you ask to every interviewee which allows you to cross-compare answers from candidates.
2. Personalized Questions: A set of questions that is unique to each candidate based on their individual backgrounds.

Let’s look at each. 

Creating and Asking Structured Questions

Busy executives often take an off-the-cuff, unstructured approach to interviews. They have an interviewee’s resume in front of them and simply ask them questions about it, probing them to discuss their background and whichever areas seem interesting or problematic. 

However, the problem with not using a structured set of questions is that they end up with no way to cross-compare the answers of interviewees. By preparing a set of common questions that every candidate answers, you can cross-compare responses and get a more concrete sense of which candidates shine in key areas.

To create structured questions, you should take into account a) the key qualities we mentioned above that you should be evaluating candidates on (problem solving, communication, etc.) and b) specific qualities or things you’re looking for in your ideal candidate.

So, for example, if reliability is really important to you, you might prepare a question to help determine whether or not candidates possess that trait (e.g. “Can you give me some examples of work scenarios that demonstrate your reliability?”). 

It’s useful to brainstorm 10 or so questions, and choose a handful of your favorites that you’ll ask every candidate. 

Creating and Asking Personalized Questions

Like structured interview questions, personalized questions for each candidate should also be prepared ahead of time. 

These are an opportunity to probe interviewees about past experiences you’re curious about, or any possible red flags—such as gaps in their work history.  

For each candidate, brainstorm a handful of these, order them based on priority, and ask them as you see fit on the day of the job interview. 

Examples of Structured Executive Assistant Interview Questions

Below are 4 common questions you can ask EA candidates. And while they may seem generic on the surface, they’re common questions for a reason. Each serves a specific purpose and draws out valuable information about the candidate.

1. What’s the hardest problem you’ve ever solved at work?

Per our emphasis on assessing problem solving ability in candidates, which determines an EAs ability to take on new and complex problems without much guidance, asking this question ensures that you directly address this key ability.

By asking it to each candidate, you can compare and contrast answers, revealing which candidates have more sophisticated, thoughtful, or detailed answers—hinting at which ones may be the best problem solvers of the group.

2. What would your previous manager describe as your biggest strength and biggest weakness?

When someone can candidly describe what their biggest weakness is and give a convincing response, they demonstrate a willingness to be honest, the ability to be self-reflective, and a willingness to grow. In addition, they indicate they’re likely to be more accepting of and responsive to critical feedback. All of these qualities are widely valued by executives and potential employers.

By pairing this with asking about their biggest strength, it provides the opportunity to understand what that candidate’s superpower might be, hinting at the areas you may find them most useful (and whether or not their strengths might match your greatest needs).

3. Where do you see yourself in 5 years?

By asking about where candidates see themselves going in the future, you can see the extent to which they’re ambitious and goal oriented. Someone who thinks ahead and plans for the future is often likely to perform according to those goals for growth.

On the other hand, if someone is uncertain about their goals, or not clear about where they’re headed, they may be less serious about the role or less interested in growing as a professional—both of which tend not to lead to great outcomes when hiring EAs.

4. Why do you want this role and why would you be a good fit for me?

Finally, this question puts candidates on the spot and prompts them to give you their most compelling pitch as to why you should hire them. It allows you to see how much thought they’ve put into understanding the role of an executive assistant, specifically as it relates to your business and individualized needs. 

At the same time, it helps you weed out candidates who may not be as committed, or may not have put as much thought into what it would mean to take on an executive assistant job with you.

How to Execute Work Sample Tests and Reference Checks

As we mentioned above, while interviews are necessary, they aren’t sufficient for thoroughly vetting EA candidates. In this section, we’ll briefly cover two other key steps worth prioritizing in your hiring process: work sample tests and reference checks.

Work Sample Tests

Unlike interviews, work sample tests require EA candidates to show you their work. They go beyond the theoretical and hypothetical discussions in an interview, and allow you to see the quality of their output in real-world situations.

While it takes additional time and effort to come up with the exercises, explain them to candidates, and review each candidates’ deliverables, it’s likely the best tool that employers have to ensure they hire someone who has what it takes to perform in an EA role.

When designing work sample tests, consider the specific things you want them to do on the job, and create your tests based on those tasks and activities. For example:

• Travel arrangements: If you want them to make business travel arrangements for you, you might have them draft an itinerary, or research flights and places to stay, and deliver you a document organizing their findings and suggestions.
• Email management: If you want them to manage your email, you might give them a series of email scenarios and ask them to explain how they’d handle each one. 
• Lead generation: If you want them to help out with lead gen, you might have them create a prospect list of potential customers, asking them to do research and find contact information for companies that fit your ideal customer profile. 

By reviewing deliverables of each candidate based on 3 to 5 work sample projects, you’ll gain a much clearer idea of which candidates do the quality of work you’re looking for.

Reference Checks

Understandably, the practice of doing reference checks has become less common because a) people tend to only list references that will speak highly of them, and b) it takes time to communicate and schedule calls with references of every candidate you’re evaluating. 

If you have 5 candidates, that might mean 10 additional people to coordinate calls with and speak to, which many executives don’t have time for.

However, doing reference checks is still valuable because when you hear negative things from past employers about performance, it’s likely you’d experience the same issues if you were to hire them. A short call has a decent chance of sparing you a mis-hire.

In our experience, there are two key aspects of effective reference checks:

1. You use a structured set of questions like you do in the candidate job interview.
2. You give candidates less latitude in who they can list as references (e.g. specifying they can only list references of their direct supervisors from the last 3 positions on their resume).

For more information on how to do reference checks properly, including a series of example questions, check out our post on how to hire virtual assistants.

The Methodology We Built to Find World-Class Executive Assistants for Our Clients

Throughout this post, we’ve discussed how to interview and evaluate EA candidates more thoroughly by using structured questions, facilitating work sample tests, and performing reference checks. 

Through reading, it’s likely become clear that executing this process effectively takes a lot of time and effort, which is why we started our executive assistant service 4 years ago.

We wanted to develop a more thorough vetting process that yielded great outcomes for executives on a consistent basis, without them needing to do all the work of hiring internally. 

The methodology we designed focuses on evaluating candidates on the 4 key qualities we described earlier (the ones that have been found to predict success in an EA role): 

1. Problem solving ability
2. Key character and behavioral qualities
3. Communication ability
4. Tech-savviness

To measure these qualities, we use a tailored combination of the following:

• Quantitative assessments: Tests that allow us to evaluate candidates accurately on key generalist abilities. 
• Structured interviews: A strategic interview process to cross-compare candidates on the qualities and abilities that matter.
• Work sample projects: Mock projects to see the quality of their work, based on the types of tasks they’re likely to do in a VA role.
• Communication exercises: Exercises to evaluate candidates on key communication skills such as email etiquette. 
• Reference and background checks: A structured approach to interviewing candidates’ references.

As a result of our more thorough vetting process, we’re able to provide EAs that grow to manage far more than calendars and email inboxes. 

Generally, our EAs manage some combination of the following for our clients:

• Communications: Manage email, communicate on an executive’s behalf and alongside them with company staff members and key stakeholders, sit in on phone calls, etc.
• Scheduling and time management: Manage an executive’s calendar, schedule internal and external meetings and appointments, resolve scheduling issues, balance personal appointments with work meetings.
• Project management: Manage the CEO’s to-dos, ensure they stay up to date and on track with their key projects.
• Business operations: Help create, organize, and improve on internal business processes and standard operating procedures.
• Marketing and social media management: Create and schedule social media posts on top platforms like LinkedIn and Facebook, monitor engagement metrics, respond to comments, help grow an overall online presence. 
• People operations: Manage employee onboarding, assist in the employee recruitment process (e.g. reviewing resumes and cover letters for certain criteria), manage payroll, etc.
• Strategic planning: Work with the company leaders to define and come up with plans for new products, initiatives, and services. Project manage some or all of these new company programs. 
• Client services: Handle important interactions with clients. Provide ideas and feedback about how to improve systems and processes.
• Special projects: Manage a wide variety of unique projects depending on what your executive needs. For example, our EAs have worked on things like web design, video editing, designing Microsoft Office PowerPoint presentations, event planning, workflow design, building data sets, and more.
• Personal assistant tasks: Help make online orders, reservations, travel arrangements, and other accommodations for executives’ personal lives.

Want to Shortcut the Hiring Process? Try Our Remote Executive Assistant Service.

We serve C-level executives and entrepreneurs at fast-growing startups across the U.S.—in cities like Los Angeles, San Francisco, Boston, Austin, Miami, and New York—and internationally.

We require no long-term commitments and can work with executives in any timezone.

Here’s how to get started with us: 

• Step 1: Complete our form to let us know your needs. 
• Step 2: If you’re a good fit, we’ll set up a call to discuss our service with you.
• Step 3: Our team will hand pick an assistant who we think will be a great fit for you based on your needs.
• Step 4: Our talent team will guide you through the onboarding process over 2-3 weeks.
• Step 5: For a flat monthly rate, you get a world-class assistant that equates to a full-time employee (40 hours of remote work per week, with no long-term commitment needed).

If you’re ready to try a remote executive assistant that can be truly transformative for your business, click here to get started. For testimonials from our clients, check out our homepage.