Best Interview Questions for Remote Executive Assistants

The Best Interview Questions We Always Ask to Hire Ridiculously Talented Remote Executive Assistants

Interview Questions Executive Assistant

If you asked me how many Executive Assistant candidates I have interviewed and hired in my career, I would reply that I have lost count.

As a senior Talent Acquisition Specialist at Headroom Assistance, I have had the opportunity to interview hundreds of aspiring and senior assistants. Through my years-long career, I figured out exactly what makes a great EA. So I’ve decided to share a list of the 10 best executive assistant interview questions I always ask that will help you find the perfect candidate for your company.

Let’s dive into it!

The best interview questions to ask when hiring a Remote Executive Assistant

First and foremost, I always ask about a candidate’s motivation. Why do they want this role? Why our start-up or scale-up company? Like interviewing for any other role, I’m looking for a clear answer that shows that they are motivated by our company’s mission, working style, and values.

I also ask candidates about their work ethics and how they handle pressure. Providing a practical example from their previous job (like one of our Senior EA did during their interview) can be a great way to showcase this. In other words, I want to know what they think they can bring to the table and how our company can fit into their bigger career goals.

This is the first step to filter out people who don’t have a real career drive. From experience, I met several VA/EA candidates who saw the job just as a temporary gig, as a side-hustle until they would find something else. And that’s not what I’m looking for when recruiting a premium assistant.

Here are 10 key questions I find particularly helpful:

  1. What do you believe are the most important qualities for an executive assistant to have?

    A great way to see how a candidate understands the role and priorities of an executive assistant and what qualities they believe they need to succeed in this position. It also gives me a good insight into their values and work style. They may prioritize different qualities based on their own experiences and preferences.

  2. How do you manage competing priorities and deadlines?

    Executive assistants need to master the art of juggling tasks and prioritizing. Asking this question helps me understand how the candidate approaches prioritization and time management. What I expect is them highlighting their organizational skills, ability to prioritize, and strategies for ensuring nothing falls through the cracks.

  3. Can you give an example of a time when you had to handle a difficult situation on behalf of your executive?

    This is one of my favorite questions to ask: it helps me assess the candidate’s problem-solving skills and ability to handle high-pressure situations – because when stuff hits the fan, I need to make sure they will keep their cool!

    It also gives good insight into their communication style and how they interact with their executive when things go south. A good candidate will be able to give me a specific example of a challenging situation they faced, describe how they handled it, and the outcome using the STAR structure.

  4. How do you prioritize your workload?

    EAs must manage a virtually endless list of tasks and competing priorities while ensuring that their executive’s needs are met. So I need to make sure the candidate’s organizational and time management skills are on point. A good candidate will have a clear system for prioritizing tasks and will be able to explain how they ensure that urgent tasks are completed first.

  5. Can you describe your experience with calendar management and scheduling?

    Here we’re looking for solid experience using calendar software and will be able to describe how they manage scheduling conflicts. Effective calendar management and scheduling are essential skills for an executive assistant. Ask this to find out the candidate’s ability to manage complex schedules and inboxes, coordinate meetings, and ensure that their executive is on time and prepared for each appointment.

  6. What do you want to achieve in this role?

    What are their career goals and their motivations for applying for this position? This question will give you some insights into the candidate’s personality and work style. A good one will have a clear idea of what they want to achieve in the role and should explain how their goals align with the company’s mission and values.
    You can read how Headroom EA Marylva sees her career development as an assistant.

  7. Suppose you had to hire a candidate for this position, what points would you pay attention to?

    I often ask this questions to see if the candidate really understand the skills and qualities required for an executive assistant role. It also gives me insight into their recruiting and hiring skills (you never know, they might need to help with job descriptions and hiring new colleagues). A good candidate should be able to identify the most important qualities of an executive assistant, such as communication skills, attention to detail, and adaptability.

  8. What has been your greatest learning in career or life, and who is your role model?

    With this question, we’re diving deeper into the candidate’s personality, values, and resilience. It provides insight into their ability to learn from challenges and their level of self-awareness.

  9. Name three of your favorite traits you have and one you wish you had.

    This applies to any candidate and is a great question to assess their self-awareness and ability to reflect on their strengths and weaknesses. Because nobody is perfect!

  10. Can you give me examples of when you’ve had to exercise discretion and confidentiality?

    As an executive assistant, your candidate will have access to sensitive information. Make sure they have experience handling confidential information with discretion and professionalism.

How to Interview an Executive Assistant – proven & tested by a pro EA recruiter

When interviewing an executive assistant, the thing to look out for is excellent communication skills, someone who is organized and detail-oriented, and can handle multiple tasks at once. Pay close attention to their past experiences and how they have handled challenging situations. Also, make sure to ask questions that are specific to your company and the role that the executive assistant will be filling:

Is the EA expected to assist the CXO only, or the entire team? Do you need them in the office or remote? What type of tasks will they be responsible for? Based on the answers, you might need an EA with a specific set of skills and backgrounds – so I recommend you keep in mind what the job description is while doing interviews.

At Headroom, we also try to include a short assessment or test to evaluate a candidate’s skills. This can be an excellent way to verify that they possess the necessary skills to succeed in the role.

Skills to look for in an A+ Remote Executive Assistant

In addition to the above questions, I always need to evaluate a candidate’s ability to work remotely. Here are some critical skills to look for:

  1. Experience working remotely and managing remote teams
  2. Proficiency with remote collaboration tools like Zoom, Google Meet, Notion, Trello, and Slack
  3. Top-notch written and verbal communication skills
  4. Strong organizational and time-management skills
  5. Self-motivation and the ability to work independently

I’ve hunted for top EAs for years now and I can confirm: finding the right executive assistant can be a daunting task. But if you ask the right questions during the interview process, you can make sure that you are hiring the best candidate for the job. Just use my executive assistant interview questions as a guide to help you find the perfect fit for your company.

Alternatively, you can consider outsourcing the hiring, training and managing to a full EA service!

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