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Ethan Bull 10 min read

Top 10 Questions To Ask When Hiring an Executive Assistant

There comes a time when business leaders recognize that balancing their growing workload is causing them to drop the ball professionally and personally.

The first question that we encounter when speaking with CEOs, c-suite executives, business owners, and non-executive board members who are considering adding daily executive support like a fractional executive assistant to their lives is: What will an executive assistant do for me?

We guide our clients to start thinking from a different perspective- one that allows them to see that there is an attainable reality where they don't have to be constantly "doing everything" to keep their business running.

The most important question you can ask yourself is: What do I need out of an executive assistant?

From there, you will be able to determine whether or not it's time to delegate parts of your workload to an experienced executive assistant to elevate your professional and personal life.

From our experience, those CEOs, c-suite executives, business owners, and non-executive board members feel immense pressure to "do it all themselves." We've seen that they have a hard time letting go of tasks, calls, meetings, and many other more complex business functions that can be easily handled by an experienced executive assistant. However, this habit of taking on too much is hard to break, and often times the thought of onboarding an executive assistant feels like another task being added to their ever-growing list.

Not sure if you need added support as you grow your business or serve on several director boards?

Here are our top 10 questions to ask yourself if you're considering hiring an executive assistant: 

  1. Does your stress level rise when you think about your schedule?
  2. Does your email inbox contain more than 50 messages or date back more than one month?
  3. Do you overpay or settle for second-rate flights and hotels because you book last minute?
  4. Are you constantly interrupted by emails, texts and DMs during calls and meetings?
  5. Are all of the payments coming into your business logged and processed?
  6. Do you have reminders scheduled ahead of significant events to allow ample time to plan?
  7. Do you want to throw an event but have no one to handle the research, details and logistics?
  8. Do you ever miss an email from a client, prospect or customer?
  9. How much time do you spend volleying emails back and forth to get something on the calendar?
  10. Would you like someone serving as your personal single point of contact to handle all of
    the above and more?

If the questions above resonate with you, then it's time to hire an in-person, remote, or virtual executive assistant

A strong executive assistant will be able to handle all of the tasks that slow you down or give you anxiety, as well as act as your project manager, chief of staff, personal assistant, and executive support all-in-one. Your future executive assistant should be able to manage your calendar, organize your schedule, book cost-effective travel, manage your staff, throw an event, and elevate your personal and professional life. They'll be able to handle:

  • Resolving double-booked meetings
  • Adding meetings to your schedule while you’re on a flight
  • Relieving your anxiety by organizing your weekly, quarterly, and annual schedules
  • Flagging messages for follow-up that you otherwise might miss
  • Canceling your hotel room before the deadline
  • Delivering an easily accessible agenda for the conference you’re attending
  • Managing flight and hotel refunds
  • Planning out your commute so that you are early to flights, meetings, and events
  • Contacting the necessary people in the event that your flight is delayed or your ride has put you behind schedule
  • Reminding you of event details and attire for networking events
  • Organizing your business and personal calendars in one place so you can easily view them side by side
  • Blocking out time in your calendar for important meetings that require preparation in the days prior



We get the hesitation that comes with handing your work off to someone new

Our team at ProAssisting consists of seasoned remote executive assistants who utilize our highly detailed Client Onboarding Process to allay that hesitation. We only partner our clients with top-level executive assistants who have years of experience onboarding numerous executives and business leaders.

We use our Client Onboarding Questionnaire to lessen the learning curve on getting to know
your preferences, personal information, VIP contacts, and a whole host of other information that smooths the onboarding process. We also provide our new clients with tips and tricks to get everyone around them to lean into their new assistant and fully utilize the range of support they can provide.


If you would like to view our Onboarding Questionnaire that we provide to our new clients, you can download it below.


Onboarding Executive Assistant | Download Free Questionnaire | Remote Executive Assistant


Ethan Bull

Co-Founder of ProAssisting

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