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How To Find A Reliable Remote Executive Assistant

Written by: Sandra Lewis

The questions of how to achieve increased efficiency, greater productivity, and less overwhelm are on the minds of business owners, entrepreneurs, and executives daily.

One of the most popular options for achieving all three is to delegate, particularly to a trusted executive assistant. And as remote work has continued to become the norm, finding a remote executive assistant has made the process of using a talented administrative professional easier than ever.

However, one thing that can really dampen your enthusiasm for bringing on a remote executive assistant is not being able to determine with confidence that the person will be a reliable teammate and a skilled professional.

Luckily, there are a few key things you can look out for to give you confidence. With these things in mind you really can hire a reliable remote executive assistant, someone who can help you achieve your goals for successful delegation.

Run through this list of questions when interviewing candidates or looking into remote executive assistant solutions to test whether or not they’ll adequately live up to your expectations. After all, the worst thing is wasting time in a process that’s supposed to bring you max efficiency.

What’s Their Experience?

Is this a side-gig?

When speaking to the remote executive assistant or remote staffing provider, ask the question, “is this a side-gig for your remote executive assistants or is this something they do as a career?”

Because many remote EA’s work fractionally, a lot of companies or solutions let them sign on to do the work as a side-gig to their other job(s). This can cause some issues when it comes to availability, dedication, and retainment. And those issues can end up costing you, the client in time and money wasted.

Before you sign onto any solution or bring someone on to work with you, be sure they’re focused and dedicated to the work.

What’s their track record?

Another factor to consider in the remote executive assistant’s experience is whether or not they have a successful track record, and what type of clients they’ve worked for in the past.

Is there a past list of clients of a similar caliber as your business? Are they familiar with your industry (which will help shorten their learning curve) and are they at the experience level you need?

For example, someone who is going to be running the back end of your business and communicating with clients on your behalf should ideally have a solid 7+ years of experience under their belt.

If you’re just looking for someone to schedule a meeting now and then and take on some simple research, you could look for someone with much less experience. (Check out this article delves deeper into how to find the right type of remote executive assistant for you.)

As a last step, check references (make sure they are professional), ask for past examples of successes and check out the online reputation of your remote executive assistant or staffing provider. This will give you great insight into how reliable they have been to clients thus far. (Websites like are a great place to start.)

Are They Happy?

When we talk about remote executive assistant solutions or providers, we’re referring to companies that manage the process of bringing on your remote executive assistants. Most virtual assistant companies hire their team as contractors (Except Boldly, who hires them as W2 employees, which we’ll discuss in further detail below.)

Considering your remote executive assistants’ happiness at their current company is of vital importance when weighing how reliable they will be for you. Do you know the company is investing heavily in keeping them satisfied in their role and therefore helping to retain them? If not, is it worth it for you to begin working with someone who may leave in the very near future?

What are the Glassdoor reviews like for the company you’re working with? Do their people seem genuinely happy and satisfied?

What are the values of the company or solution you’re planning to work with and does their culture match your own? If you feel the values and culture of the company or solution that the remote executive assistant works for aren’t a good match with yours, odds are the assistants themselves won’t be a great match either.

Do They Feel Secure?

As we mentioned, almost all remote staffing companies who offer executive assistance hire their team as contractors (except Boldly). This is something you need to think about from a few different angles, as feelings of instability can often lead to unreliability in any team member.

Ask these questions:

  • Since this person is a contractor, do they have clients coming and going at all times with no continuity? Or is their work pretty stable, allowing them to make a predictable income.
  • Does the provider allow for clients to use rollover hours? Rollover hours can cause a lot of instability. (This article discusses why rollover hours for clients of remote executive assistants can cause scheduling problems for both parties.)
  • Where is the remote executive assistant getting their benefits? Do they have the health coverage they need? Are they covered by liability insurance?
  • And perhaps the biggest question to ask to protect yourself as a client: are they working compliantly?

What’s Their Pay?

If you’ve never worked with a remote executive assistant, you may be thinking about starting with a less expensive option just to get your feet wet. However, if you’re looking for a true partner in a remote executive assistant, someone you can fully trust and fully rely on, then the old adage “you get what you pay for” really rings true.

Read more about how much you should pay for an executive assistant.

If you want someone high-quality you can work closely with for the long-term, going with the cheapest option can often lead to frustration, wasted time, and an overall unpleasant experience.

To avoid your search for a reliable remote executive assistant becoming a bigger headache than it’s worth, you need to calculate the value of that remote executive assistant to you and pay accordingly. (Note that you’ll already be saving quite a bit in hiring a remote assistant or fractional executive assistant, as hiring someone in-house on average costs $4k and takes around 52 days!)

Perhaps the biggest factor in determining if you will have a reliable remote executive assistant is to think about retention and how it fits into your ROI. Put quite simply, investing in someone who is going to stick around for the long-term will give you a better ROI in the end, as this person will learn your business, learn your needs, and begin to anticipate what you need before you even have to ask.

If that is the type of person you are looking for, you may want to consider using a subscription staffing solution.

Finding A Reliable Remote Executive Assistant Through Subscription Staffing

If you’ve decided that you do want a true partner and a trusted and reliable remote executive assistant, using a subscription staffing solution might be right for you. Subscription staffing through Boldly ensures that our remote executive assistants will be reliable teammates for our clients by doing the following:

  • Employing our team as W2 employees which makes them a compliant long-term solution, gives them the stability of employment plus benefits
  • Continually investing in their happiness as employees so they can be the best possible resources for our clients, and also stay with us for the long-term
  • Paying a wage that is higher than our competitors, and offering our assistants paid time off, paid holidays and other benefits
  • Only hiring executive assistants with 7+ years of professional experience (or more!)
  • Putting our executive assistants through a thorough vetting process, hiring only 0.001% of candidates who apply.

If you’re interested in learning more about how to find a reliable remote executive assistant, subscribe to our blog using the form below. If you would like more information on how to get started with a remote executive assistant from Boldly, get in touch!

Topic: Remote Executive Assistant

Updated on October 12th, 2023

About the author: Sandra Lewis is the Founder and CEO of Boldly. She's passionate about helping Businesses, Organizations and Executives increase productivity and move their work forward with the right skills and resources. Setting an example of the efficiencies gained working remotely, she’s been leading her entire team on a virtual basis for the past decade.