Hiring an executive assistant is a high-stakes decision for any founder or executive. The right person will be your right hand; they’ll manage your schedule, streamline operations, and give you back your time. But how do you know if a candidate truly fits the executive assistant role?

In this guide, you’ll learn how to leverage executive assistant interview questions to get the right person for the job. Also, we’ll cover how to structure an executive assistant interview and potential red flags to watch out for.

Let’s get started!

TL;DR – Interview Questions for an Executive Assistant

Hiring an executive assistant is more than just getting someone to whom you can delegate tasks. You owe yourself an executive assistant you can trust to take the lead even in high-impact situations.

We have compiled 10+ questions to ask an executive assistant to help you cover key areas, including:

  • Background and career path
  • Project ownership and problem-solving
  • Calendar, email, and time management
  • Communication and confidentiality
  • Tools, technology, and adaptability

But if you are experiencing scheduling bottlenecks and need an executive assistant to hit the ground running, work with us.

At ProAssisting, we have 5+ years of experience helping busy executives and founders hire experienced executive assistants who wear multiple hats, including business partner, chief of staff, assistant scheduler, project manager, and personal assistant.

Schedule a one-on-one consultation to learn how our ProAssistants can support you!

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Why Hiring the Right Executive Assistant Is Critical

Once you land the right executive assistant, you can never go back. They take the administrative overheads off your shoulders so you can have more time to pursue high-impact goals or take a break.

Below are the key incentives of hiring a full-time or fractional executive assistant:

  • Freed-Up Time: The be-all and end-all of hiring an executive assistant is to ‘get your time back.’ The right EA can save you 15-20 hours weekly, which lets you focus on your core business functions.
  • Professional Representative: You want to feel comfortable having your EA interact with everyone within and outside of your business, including clients, vendors, associates, and all other stakeholders.
  • De Facto Project Manager: A good executive assistant will also double up as your pinch hitter, handling projects and responsibilities outside of their EA role to make your day less stressful.
  • Streamlined Communication: The right executive assistant provides a single point of contact for anyone seeking information or clarification from your office/role.
  • Business Partner: Lastly, the best-fit executive assistant will feel like an associate or strategic partner. They’ll quickly learn how you think so they can provide high-level support and help make plans while maintaining confidentiality.
Senior team reviewing printed financial reports in office boardroom.

How to Structure an Executive Assistant Interview

Remember, the executive assistant you hire will often be the ‘face’ of your business. So you want an assistant with whom you are comfortable interacting with your staff, and sometimes, family and friends.

The best guarantee of getting the right executive assistant is to make the interview process as thorough as possible.

Here are some practical tips to help you structure your EA interview:

  • Start with Small Talk: Use icebreaker questions to build rapport with the EA candidates. This also helps you get a feel of how they’d have similar small talk interactions with your clients, vendors, and other executives. For example, you could ask what they think of the weather or how many kids they have.
  • Educational Background: Check the candidate’s educational background and how it aligns with the EA role. Usually, it is not compulsory that a candidate must have gone to college, but they should at least be getting certificates or enrolling in courses relating to EA-focused software or skills relevant to working in a service-based business.
  • Career Trajectory: Review each candidate’s career story in detail and seek clarification about gaps in their resumes. Also, drill down into the bullet points about their duties and responsibilities in the last two or three EA roles. Finally, find out why the left or want to leave their current role.
  • Tasks, Projects, and Responsibilities: Ask the candidates to share some memorable challenges they faced when working for previous principals and how they overcame them.
Business professionals in a meeting discussing documents.

Top 15 Executive Assistant Interview Questions

Ready to find a ‘mini-me EA’ who can juggle calendars, guard your time, and think several steps ahead? These 15 executive assistant interview questions will help you identify which candidate is truly executive-ready.

Background and Career Path Questions

Ask these questions to evaluate the candidates’ experience level, executive exposure, career goals, and alignment with the role.

Here are some practical questions about educational and career background:

  1. Please explain the gaps in your work experience. Why did you leave your last two employers, and why are you looking to get back to EA work?
  2. Walk me through your experience as an executive assistant. What were some of your key responsibilities and achievements?
  3. Tell me about a past role where you supported a C-suite executive. What was the scope of your responsibilities?

Project Ownership and Problem-Solving

These questions help you assess the candidates’ organizational skills, ability to multitask under pressure, and strategic thinking in prioritization. They’ll also help you gauge each candidate’s foresight, initiative, and ability to be a true partner to an executive.

Example questions include:

  1. Share an instance where you had to make a decision on behalf of your executive. What was the outcome?
  2. Tell me about a time you had to step into a leadership role unexpectedly. What was the experience, and how did you ensure all stakeholders were informed and deadlines were met?
  3. Give me an example of a time you anticipated a need for your executive and proactively addressed it. What was the outcome?
Woman in headset taking notes during a video call at home.

Calendar, Email, and Time Management

Your aim for these questions should be to understand each candidate’s ability to customize support based on individual executive needs. Also, evaluate each candidate’s communication finesse and capacity to balance an executive’s personal work rhythm with urgent business demands.

Consider the following questions:

  1. Describe a time you had to manage multiple conflicting priorities and tight deadlines. How did you prioritize the tasks and ensure everything was completed on time?
  2. Give me an example of when you had to manage an executive’s schedule where their preferred working style (sacred ‘work out’ times or specific focus blocks) conflicted with an urgent external request. How did you find a resolution that honored their preferences while meeting business needs?
  3. How would you integrate email management with calendar planning to ensure urgent communications are addressed without overwhelming your executive?

Communication and Confidentiality

Communication and confidentiality questions help you assess the candidates’ interpersonal skills, emotional intelligence, and ability to adapt their communication for maximum effectiveness. Also, this is an opportunity to gauge whether candidates understand the impact of confidentiality, trustworthiness, and ethical conduct in the EA role.

Here are some guiding questions to consider:

  1. How did you handle communication and confidentiality as an executive assistant with your previous principal?
  2. What other ways have you seen communication and confidentiality handled in the past?
  3. Highlight a situation where you had access to highly confidential information. How did you ensure its security and discretion?
A busy professional working on a laptop, reviewing documents, and talking on the phone in a coworking space.

Tools, Technology, and Adaptability

Test the candidates’ openness to change, curiosity, and readiness to support evolving tech environments. Also, gauge each candidate’s strategic thinking and ability to match technology solutions with business needs.

Consider the following questions:

  1. On a scale of 1-10, how adaptable are you to new technology platforms and tools related to the EA role?
  2. How do you decide which tool or platform is best for a specific task (e.g., scheduling, tracking, project management)?
  3. Please explain your process when evaluating the category of a new tool, such as a CRM, project management platform, or calendar software, so you can effectively integrate it into an executive’s workflow.

Here’s the truth: conducting executive assistant interviews is hectic and time-consuming. Even then, you have no guarantee that the candidate you settle for will meet your support needs.

At ProAssisting, we help executives bypass this process by providing pre-screened EAs with at least 5+ years of experience supporting C-suites. Also, you can scale the level of support quickly by shifting from a fractional to a full-time EA without going through another round of interviews.

Book a free, no-obligation call today to learn how our ProAssistants can help you become more productive!

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Red Flags to Watch Out for During EA Interviews

Below are key red flags to look out for when hiring an executive assistant:

  • Lack of Empathy: Be wary of EA candidates who talk negatively about previous executives. Such candidates are high-risk as they could equally badmouth you in the future.
  • Lack of Confidentiality: While honesty is a positive trait in an executive assistant role, avoid candidates who readily share private information about past executives.
  • Poor Communication Skills: Watch out for EA candidates who cannot express themselves coherently or explain basic concepts logically. This is because they will likely struggle to articulate your business to clients, costing you business.
  • No Ownership Mindset: Candidates who blame others for their failure will likely avoid accountability and require micromanagement. Also, avoid candidates who lack initiative, especially in high-pressure situations, and only wait for instructions.
  • Job-Hopping Without Explanation: Candidates who change roles every few months are a red flag because you cannot trust them with long-term planning or leverage their skills for relationship-building. Also, they might jump ship during peak seasons, leaving you in a crisis.
A woman in a blazer conducting a remote meeting from a stylish café with a laptop and coffee.

What a Great EA Interview Answer Looks Like

Now that you know which red flags to avoid, it is equally important to know what makes a good answer during EA interviews. The responses should demonstrate initiative, clarity, and confidence. Here’s what to look out for:

  • Conversational: The candidate should speak naturally, confidently, and come across as genuine and approachable. Also, while preparation is good, the answers should not feel rehearsed.
  • Clear Answers: The responses should demonstrate the candidate’s ability to convey information logically. For instance, answers that follow the STAR (situation, task, action, and result) method suggest a candidate will also excel at written and verbal communication.
  • Follow-Up Questions: A good interview answer could include a follow-up question as the candidate seeks clarification about the role. It shows the candidate is already thinking critically about how they’ll support you.
Two professionals collaborating on a laptop, reviewing financial charts and reports over coffee.

Interview Tips for Founders and Executives

Your approach when interviewing EA candidates should basically be, “These are my issues; how would you solve them?”

Here’s my cheat sheet when interviewing candidates for an executive assistant role:

  • Prioritize C-Level Experience: Find out which candidates have experience providing C-level support and narrow down how they’d leverage their executive assistance skills to free up your time or address scheduling bottlenecks.
  • Check for Discretion: Always assess the EA candidate’s understanding and perception of confidentiality. What does it mean to them? How far are they willing to go to safeguard private information?
  • Have a Good Interview Strategy: Just like the candidates prepare for the interview, it is also paramount that the hiring executives plan how they’ll facilitate the session. For instance, you could ask some of the questions compiled in this guide for deeper insights into different candidates’ suitability for the EA role.
Close-up of hands writing in a notebook during a meeting.

Frequently Asked Questions (FAQs)

Got pending questions?

Let’s answer commonly asked questions about executive assistant interviews.

What Should I Look for on an Executive Assistant’s Resume?

Here are the main things to look for on an executive assistant’s resume:

  • Experience in the executive assistant role.
  • Proficiency in EA-related tools like G-Suite, MS Office, and Slack.
  • Achievements or impact statements on how they helped previous executives.
  • Essential soft skills like time management, discretion, adaptability, and attention to detail.

How Long Should an Executive Assistant Interview Last?

There’s no specific timeline for how long an executive assistant interview should last. It depends on the role’s specific needs, the number of interviewers, and whether the candidates will undertake practical tests. However, most interviews last between 30 and 90 minutes.

How Much Should I Pay an Executive Assistant?

There’s no one-size-fits-all amount regarding how much you should pay an executive assistant. You must account for the executive assistant’s years of experience, work hours (full-time vs. part-time), work arrangement (in-office, hybrid, or remote), tech stack (knowledge of relevant platforms like Notion, Slack, Asana, and other CRMs), and level of support. With ProAssist, you’ll pay a fixed monthly retainer starting at $3,300.

What Are Good Icebreaker Questions for EA Interviews?

Icebreaker questions are a great way to lower tension in the interview room and get a first impression of the EA candidate. Some good icebreaker questions for EA interviews include:

  • What’s your favorite hobby, and how often do you indulge?
  • Suppose you could instantly master a new skill. Which skill would you choose?
  • Which state would you choose if you could live anywhere for this role?

Conclusion

Hiring an executive assistant is the first step toward getting up to 15 hours of your time back every week. The right match becomes integrated into your executive roles, so they feel like an extension of you.

However, the best way to land a resourceful executive assistant is by conducting a thorough interview.

But if you are currently overwhelmed and cannot spare time for executive assistant interviews, consider partnering with ProAssisting.

Our ProAssistants have at least 5 years of experience supporting high-level executives. Also, we maintain a 3:1 executive-to-assistant ratio, ensuring your assigned ProAssistant is available whenever you need them.

Ready to reclaim your time at a fraction (50 to 80% less) of the cost of hiring an in-house PA? Schedule a free consultation with us today!