20 Interview Questions to Ask When Hiring an Executive Assistant in 2024

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A man smiling while being asked executive assistant interview questions on a video call.

What executive assistant interview questions should I be asking potential candidates?

You’ve done it. You’ve scrolled through digital stacks of resumes and you’ve narrowed it down to a select few. They’ve got impressive resumes and well-written cover letters, but now the next step is the initial interview. You might even have a few interview questions for your job candidates ready. Maybe you’re completely new to this and you don’t even know what to ask. 

Whatever the case, we’re here to help with 20 questions covering topics like skills, experience, behavior, and career goals. 

Interview Questions to Evaluate Candidates’ Skills and Qualifications

1. Can you describe your previous experience as an executive assistant & the specific tasks & responsibilities you handled?

This question gives you a great overview of their experience and what they can bring to the table. This gives you a chance to compare their answers to what they’ve written on their resume and cover letter. You can also ask about specific experiences they’ve listed on either of these application documents. It’s important to keep note of this because this sets the expectation of what they can deliver. 

2. How do you prioritize tasks when faced with multiple deadlines?

An executive assistant (EA) should be no stranger to juggling tasks. This question gives you insight into their work and productivity habits and their discipline when it comes to getting things done. It also reveals their ability to judge which tasks require more time and effort to complete. Do they know how to categorize tasks, divide their efforts, and set apart adequate time for each? Time management and organization are two qualities that are crucial to prevent dropping the ball.  

3. Describe a situation where you had to handle confidential information. How did you maintain discretion?

It isn’t uncommon for executive assistants to handle sensitive company, partner, or customer data. Based on the way they answer this question, you’ll know if they are someone trustworthy. Even the way they talk about the topic itself can already clue you in. Are they aware of secure methods of storing and sending data? Are they familiar with confidentiality agreements? 

Two women handling confidential documents.

4. How do you handle situations where an executive is unprepared for a meeting?

This isn’t to say executives are sloppy or uninvolved. The reality is, sometimes these high-ranking businessmen are constantly jumping from one important thing to another. I mean, that’s one reason they would need an EA in the first place. 

This is about seeing how resourceful and adaptable EAs are. Can they condense information and get executives up to speed quickly? 

Also, on top of these general executive assistant interview questions, feel free to take opportunities to ask follow-up questions like:

  • What other steps (if any) have they taken preemptively to help their boss? 
  • Were they able to find a way to reschedule the meeting? 

5. What software tools do you use in your daily tasks as an executive assistant? How proficient are you with them?

In this age, proficiency in software is almost a “must mention”. Executive assistants have more on their plate than most assistants do and software can definitely improve their productivity and accuracy. If they know how to automate certain tasks, this means they have more bandwidth to focus on more complex ones. You can also find out if they are familiar with tools you already use internally. More than that, this gives them an opportunity to offer other technical solutions with their own expertise. 

6. Tell me about your previous experience with event planning/managing a calendar/managing an inbox.

This can show you how they organize, coordinate, and plan.They must be able to plan things months in advance. Scheduling must happen in a way that executives can complete all their obligations without one single day being overbooked. 

This also shows how effective they are at managing internal and external communications and replying to key personnel. 

7. How do you ensure effective written communication on behalf of an executive?

Here’s where a resume cover letter can be a great way to tell how effectively someone communicates. You can assess their tone, level of professionalism, etiquette, clarity, brevity, and general writing prowess. 

You can also ask if they have experience with email management. If so, this could mean they have experience responding to people of various positions. The ability to adjust tone based on who they are speaking to show valuable flexibility when communicating. 

8. What strategies do you use to manage travel arrangements, ensuring efficiency and cost-effectiveness?

Travel can get expensive and hectic. Would they think of ways to maximize all the traveling happening? Like, for instance, would they consider registering you for a frequent flier program or other passive benefits?

It’s important to have complete accommodations and comfortable travel arrangements. However, they must also know the limits of what’s modest and what’s bordering on lavish. Though, this does vary depending on the preferences of the executives. 

9. What is an accomplishment you’re proud of?

This not only shows you what they are capable of but also shows you what they value. In fact, we’d say this is one of the most insightful executive assistant interview questions you can ask. A good follow up question could center around why that accomplishment made them feel proud. This reveals what lessons they learned from that experience. Were they proud because of the hard work it took to get there? Was it because they valued helping the company succeed? Was it working alongside other talented individuals as a team?

5 hands piled on top of each other as a symbol of teamwork.

Behavioral Interview Questions to Assess Candidates’ Experience and Behavior in Certain Scenarios

10. Tell me about a time when you had to step in to represent an executive in a professional setting.

Sometimes executives cannot be present for certain meetings. They may task their EA to give a presentation, relay information, or stand in on their behalf. An EA also relays information back to the executive. 

There’s a great deal of trust put into an EA if they are to be a mouthpiece for those in top positions. Thus, an EA must be knowledgeable and well-researched on the topic. They also need to be a good spokesperson. They should be ready to answer rudimentary questions about the topic. 

11. How do you handle challenging personalities at work?

When you’re working with a team, not everyone is going to be equally enthusiastic or cooperative. Sometimes there can be a difference in opinion or idea when beginning a project. 

Butting heads can happen, but how will they be able to mitigate work conflict? This is one of the most important executive assistant interview questions.

Assess their responses and ask yourself:

  • Would they be able to keep a cool head and stay calm? 
  • Could they still communicate effectively to get deadlines met? 
  • How would they resolve conflict if it were to occur? 
  • Would they try to fix things with the person privately or go directly to HR? 

All of these are an important glimpse into their people-skills, values, professionalism, attitude, and compatibility with your company work culture. 

12. How do you handle difficult or demanding requests from other employees or executives?

This question is not simply to gauge their ability to work within a tight timeframe or under pressure. An executive assistant should be capable of handling a comparatively heavier workload than other assistants. However, it’s also about their ability to assess how plausible these demands are. Can they give a more realistic timeframe based on their experience? Are they able to communicate honestly if something is unrealistic in that time period?

However, this also reveals what their first response would be. It’s not a very good sign if their first instinct is to try and push the deadline. 

13. Can you describe a challenging situation you’ve faced as an executive assistant and how you overcame it?

This is your opportunity to evaluate their problem-solving skills, resourcefulness, and creativity. In fact, depending on the situation they describe, you can get a good feel for their soft skills, personality, and tenacity. 

Challenges also teach people something. How did they make sure that this never happened again, or how did they equip themselves afterward? 

14. Describe a time when you had to handle conflicting priorities in your work as an executive assistant.

There will be times where deadlines or tasks clash with one another. In these instances, you need someone who knows which ones take precedence over others. This can reveal their thought process and critical thinking abilities. Do they have strategies or solutions they use to help them with things like this? 

For instance, the Eisenhower Matrix or Urgent-Important Matrix is a valuable concept for any executive assistant to know. It helps sort tasks based on importance and urgency.

Eisenhower Matrix for executive assistant task management.

Additional Interview Questions to Evaluate Candidates’ Fit for the Company Culture

15. How do you stay organized in a fast-paced work environment?

With a lot to get done and with limited time, it can be easy for organization to take a back seat. It can snowball into disorder very quickly unless it’s managed. This question helps give you insight into how candidates maintain order through healthy habits or the help of software. It isn’t so much about doing everything to avoid disorganization. Rather, it’s about what they do to ensure it doesn’t stay that way and cause issues down the line.

16. How do you handle stress and pressure in your role as an executive assistant?

Morale and mental health play an important role in the workplace. The lack of a healthy outlet can be detrimental. You can ask them to describe a stressful situation and evaluate their stress response and coping strategies. A negative stress response could affect both their health and their work in the long term. 

This is one of the executive assistant interview questions that can also turn into an opportunity to build rapport with your potential hire. You can also take this opportunity to reassure your candidate that you care about a healthy work environment.                      

17. Can you provide an example of a time when you collaborated with a team to solve a problem?

”Works well with others” should be a requirement. After all, they are likely going to manage or oversee several departments of assistants. You can ask them about their role in the project and the experience of working with others. How did they overcome obstacles? How did they celebrate? Was there some kind of debrief after? 

Some insights you can glean based on their answers: 

  • Their leadership ability/ ability to delegate 
  • What they contribute to a team 
  • Their ability to take suggestions and manage people 

18. How do you anticipate the needs of an executive and proactively assist them?

The main thing this question gauges is their ability to take initiative. Initiative takes foresight and observation. Are they sharp and attentive? Do they bring attention to potential problem areas and come up with ideas to solve them before they arise?

Questions to Assess Candidates’ Long-term Goals and Career Aspirations

19. Where do you see yourself in the next five years in your career as an executive assistant?

Note their career goals and milestones. Where do they see themselves in the long term? Do they care about building their career in this field? Is this job a good stepping stone towards those goals? Does their mission align with the company’s?

20. What motivates you to continue growing and improving in your role as an executive assistant?

Driving force is important. It can mean the difference between a job-hopper and a partner. Are they in it for the money and benefits or are they growth-minded? Do they care about building a career? Are they passionate about this or are they just trying to make ends meet? Would they be a good fit for your company’s mission-vision and culture?

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Since being founded in 2020, Outsource School has helped 1,000+ business owners hire 2,000+ virtual assistants for their companies.

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The interview process can be nerve-wracking for both parties. Sometimes the difference between a good answer and a great one lies with how you frame the question. We hope these executive assistant interview questions will serve as a useful template for that next job interview. 

If you want to know why we use Slack to interview, click on over.

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