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Top 15 Executive Assistant Interview Questions: Uncover The Best Fit For Your Team

The phrase “hire slow, fire fast” is common in the business world. But sometimes the “hiring slow” part is tough, especially when you’re trying to fill an executive assistant position.

When you need an EA, you tend to need one yesterday.

Because your executive assistant will be so integral to you, connecting with clients and team members as well as accessing information that requires a high-trust level—you need to make sure they’ll be a good fit right from the start.

At Boldly, we’ve been hiring remote executive assistants for over a decade and have learned a thing or two about finding and interviewing candidates.

Here are 15 executive assistant interview questions to help you identify the best candidate, plus tips on how to end an interview and what to do next.

Understanding The Role Of An Executive Assistant

Before you can start interviewing, you’ll need to write a good executive assistant job description.

An executive assistant handles a broad range of duties that range from admin to deeper integration into projects.

This includes:

  • Managing your calendar, including setting up meetings, coordinating events, and arranging travel.
  • Sorting and responding appropriately to communications, such as email or phone.
  • Arranging and managing travel plans.
  • Responding as or on behalf of you to clients and team members.
  • Managing internal processes.
  • Bookkeeping, such as expense reports.
  • Providing research and materials needed for projects and presentations.

An executive assistant is more than someone helping you complete a task list. They are highly integrated into your team and the way you work, meaning that operations and workplace culture can be affected positively or negatively by who you choose as an EA.

If you’re wondering what executive assistant interview questions to ask, we’ve grouped them into categories to make it easier to see what you’re looking for as the candidate responds.

Key Experience-Based Executive Assistant Interview Questions

Determining the level of experience and proficiency of a candidate go hand in hand.

Interview questions for executive assistant to the CEO need to pinpoint C-Suite experience, specifically. Not all executive assistants have C-Suite experience, nor have they all handled the role the same in previous positions. Some may have experience, but not extensively.

Here are several executive assistant job interview questions that do more than provide a listing of skill sets (which you can easily see on a resume) and give the candidate a chance to provide context for their experience.

Sample Executive Assistant Interview Questions

  1. Can you describe your experience with managing schedules and handling confidential information?
  1. Share an instance where you had to make a decision on behalf of your executive.
  1. What strategies do you use to manage heavy workloads and tight deadlines?

Experience-based questions are what we tend to think of when we think of hiring questions, as they are a bit easier to quantify.

Read more: How Much Experience Should Your Executive Assistant Have?

Assessing Executive Assistant Working Styles And Compatibility

Less easy to discover is how well a person will fit in with workplace culture, as well as fitting in with your working style and personality. Amazing experience and long lists of skills won’t overcome a personality or culture clash.

Sample Executive Assistant Interview Questions

  1. How do you prioritize tasks when everything seems urgent?
  1. Describe your communication style. How do you ensure clarity and efficiency in your communications?
  1. Can you give an example of how you’ve adapted your working style to complement different executives?

Pay attention to the dynamics of the interview itself. If you prefer someone more assertive or outspoken, a candidate who is soft-spoken or more cautious may not be what you’re looking for. If you prefer someone more thoughtful before taking action, someone who snaps off an answer immediately might indicate someone fast to act and not what you’re looking for.

An executive assistant is someone you need to be able to completely trust, and that won’t happen if your personalities aren’t a good fit or your working styles are at odds.

Setting Clear Expectations: Questions To Ask

Some of the most important executive assistant interview questions to ask are about expectations. Fantastic experience and great compatibility, but very different expectations, are a roadmap to disaster.

Sample Executive Assistant Interview Questions

  1. What are your expectations regarding availability outside typical working hours?
  1. Can you discuss your approach to handling sensitive or confidential information?
  1. How do you approach continuous learning and professional development in your role?

An executive assistant candidate must be on the same page as you when it comes to what you expect them to accomplish or there will be significant frustrations.

It’s better to lose an excellent candidate now, because of differing expectations in time or responsibility than down the road when they’ve already been onboarded.

See also: 5 Keys To Revolutionize How You Work With An Executive Assistant [Goals + Examples]

Identifying Red Flags: What To Look Out For

Red flags are difficult to spot because the candidate isn’t going to offer them up. They might not even be aware of them, or aren’t aware that the way they worked with a previous executive would not be acceptable with you.

Sample Executive Assistant Interview Questions

  1. Have you ever faced an ethical dilemma at work? How did you handle it?
  1. Can you describe a situation where you had a conflict with a colleague or executive? How was it resolved?
  1. Tell me about a time when you missed an important deadline. What happened, and how did you manage the situation?

Watch for inconsistency in responses, both in these questions and throughout the interview. Take note of whether a response is direct and forthcoming, or hedged and evasive.

Pay close attention to how a problem, and its solution, is given context. When they describe scenarios involving previous employment, do they lack discretion in doing so? Do they seem to lack problem-solving skills or an understanding of why a solution worked?

Red flags aren’t just what they’ve done or might do. It may also be in experience gaps that keep you from knowing how they will respond in a particular situation that will happen frequently.

Scenario-Based Questions For Real-World Insights

Presenting scenarios to find out how the executive assistant candidate would respond are a great way to not only see how they think and respond, but also to get insight into how they view the context of an issue.

Sample Executive Assistant Interview Questions

  1. How would you handle a situation where two high-priority meetings overlap?
  1. Describe a time when you had to manage a crisis or unexpected challenge.
  1. If you noticed an error in an important document after it was sent out, how would you handle it?

Scenario-based questions show you how they respond under pressure with real conflicts to sift through. They are different from traditional executive assistant interview questions in that instead of focusing on behavior (past experiences), they present hypothetical future experiences that do a good job of assessing a candidate’s capability in high-pressure moments (which they will experience as an EA).

Closing The Interview: Next Steps And Feedback

How you close the interview matters whether you choose to hire the candidate or not. Remember, your reputation as a professional is also being evaluated by the candidate.

  • Before closing the interview, allow the candidate to ask you questions. Not only does it give them a sense of ownership of their own interview, but you’ll likely learn something important simply by the questions they ask.
  • Tell the candidate what they can expect next from you. Whether it’s offering them a position or informing them otherwise, they should have a clear expectation of what’s next — ideally with a timeline. It can be as simple as: “We’re hoping to fill this position within the next few weeks, so I’ll be in touch soon. When possible, provide honest but discrete feedback in a reasonable so they can learn from the interview and move forward if the position isn’t offered.
  • Be sincere and professional as you thank them for their time. Whether you’re conducting a remote interview or in-person, it’s important to compile your notes while the interview is still fresh in your mind before interviewing another candidate.

The truth is, great candidates with amazing experience, ethics, and qualifications may not be a good fit because of compatibility, not because of quality. Acting professionally and reasonably is important no matter the outcome of the interview.

How To Skip The Executive Assistant Interview

Short on time? Tired of interviewing or stuck on finding the right fit?

If you need a hire immediately or are looking to bring on several EAs at once, you can find highly qualified executive assistants through the best remote executive companies (although you’ll want to be mindful of legal compliance when you’re considering a remote staffing solution).

At Boldly, you can get ridiculously talented, high-level executive assistants—without the hiring or interviewing. Here’s how it works.

About the author Katie Hill is a Content Writer at Boldly, which offers Premium Subscription Staffing for demanding executives and founders. When she isn't writing about remote work or productivity, she can be found adventuring in Colorado's backcountry.

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