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How To Hire A Rockstar Remote Executive Assistant In 2024

Today, the case for a remote executive assistant is simple to make.

As we head towards an uncertain economic future, demands for performance continue to grow. Now more than ever, you can’t afford to be buried in an endless list of tasks and administrative duties. With the rise of fractional executive assistants (who can support multiple executives) combined with the quality and flexibility of premium subscription staffing, senior executives and business owners like you can find experienced assistants you can trust to save you and your team valuable time.

In this article, we’ll help you:

  1. Understand what preferred skills a great EA will have
  2. Define the type of person to look for
  3. Find qualified candidates quickly (without a painful application process)

Table of Contents

The Many Roles A Remote Executive Assistant Fills

While often used interchangeably, executive assistants are not the same as administrative assistants, virtual assistants, personal assistants, or even an office assistant. (Read more about the difference between a virtual assistant vs. an executive assistant.)

EAs handle a wide array of advanced duties and fill many administrative roles. They’re the Swiss Army knives of the workforce, whether they’re a full-time employee or a shared EA.

But what sets a rockstar remote executive assistant apart is their ability to handle high-trust tasks that rely on nuance, industry knowledge, and long-term relationships with other leaders.

Sure, scheduling meetings is on their resumé, but so is responding in your name to the CEO of a Fortune 500 company. So is leveraging project management expertise to reduce friction in key processes. So is ensuring that the right people get follow-ups on a multi-million dollar proposal or grant.

The best high-level EAs will immediately provide value to your bottom line.

12 Things A Remote Executive Assistant Can Do (More Than Just Email!)

Chart showing 12 things an executive assistant can do besides sending emails -- from managing schedules to bookkeeping and more.

  1. Schedule Meetings
  2. Expense Reports
  3. Research
  4. Travel Arrangements
  5. Event Coordination
  6. Email Filtering
  7. Call Screening
  8. Personal Tasks
  9. Manage Internal Processes
  10. Appointment Setting
  11. Bookkeeping
  12. Email Inbox Management

What Traits Make Someone A Successful Remote Executive Assistant?

Great remote executive assistants share common traits and interpersonal skills.

Having worked with top 1% EAs for over a decade, we’ve found 9 traits that set the best apart:

  1. Creative problem solving
  2. Social and emotional intelligence
  3. Anticipation of needs
  4. Resourcefulness
  5. The drive to see others succeed
  6. Attention to detail
  7. The ability to prioritize
  8. Excellent communication skills
  9. Building new skills

Ask specific questions during the hiring process that help you evaluate potential candidates.

For example, you could ask: “What is your greatest accomplishment?” or “What new skills have you learned in the last year to improve your performance?”

Read more: Top 15 Executive Assistant Interview Questions

Listen for answers aligned with assistant tasks and shared achievements. Rockstar EAs are motivated by helping. They’re driven to see others succeed. Ask for examples, do reference checks, and look at past work in assistant roles.

The top 1% will also be motivated to grow their skills and knowledge. For instance, how are they using new AI tools? Especially beyond ChatGPT.

How Can You Effectively Work With Remote Executive Assistants: Step By Step

Working with a remote executive assistant is a two-part equation. It takes their skillset combined with your ability to work with them (and leverage those skills).

An effective relationship has just takes a few minimum requirements from your side:

1. Delegate the Right Tasks, Forever

To start, know what to delegate from day one.

You can know exactly what tasks to hand over by keeping a list of everything you do. It might seem like a lot of busy work. But think of it like this.

Writing the task on your delegation list removes it from your to-do list forever. A remote executive administrative assistant can take over these tasks, allowing you to focus on strategic decisions and business growth.

For every task ask yourself: “Is this a strategic task that only I can do or can an EA do this for me?”

This can be everything from what office managers used to do to personal tasks just for you.

  • Sending gifts to family members? Check.
  • Making anniversary dinner reservations? Check.
  • Drafting a job description? Check.

You get the idea.

2. Let Go Of Control

Giving up control is one of the toughest parts of delegation.

If you’ve been doing administrative tasks long enough, it might seem like you’re the only one who can do it precisely the way you want it done. Or even that it will take longer to delegate than to do it yourself.

The truth is, any process can be replicated. And on the plus side, the right-fit EA won’t simply copy-and-paste. They can often find ways to improve, simplify, or eliminate tasks completely.

Once a task is dialed in, they’ll document the process. Every step will then get executed flawlessly, every time. This means enormous time-savings down the road.

And ironically, when you hire an assistant, you will feel more in control than you did before. Because now you’re getting a better result faster than you were able to produce it yourself.

Let go of control to experience the magic of an EA.

3. Find Someone You Trust

The foundation of a productive working relationship is trust. There’s no way around this.

Yes, it will take time to get them up to speed. But eventually, if you can’t hand over the proverbial keys, you haven’t found the right fit.

Trust is partly based on someone’s past performance. But there are other factors at play, as well.

Here’s how to find an executive assistant who you’ll trust.

3 Ways To Find A Rockstar Remote Executive Assistant

1. Hire For The Role Directly

First up, to hire directly, get your job descriptions ready. A tightly-defined executive assistant job description is mission-critical so you get the right applicants.

You can follow a hiring process to bring them on as a W2. However, you’ll need the time, bandwidth, and budget to recruit them.

This means things like:

  • Paying current employees to work the recruiting process
  • Promoting the position with your advertising manager
  • Managing responses
  • Conducting in-person interviews or remote interviews
  • Reviewing resumés like experienced recruiters
  • And plenty more!

You’ll also need to go through the process of becoming compliant for hiring remotely.

Then, once the employee is hired, you begin the process of training.

Today, you can expect to pay anywhere from $4,000 to $20,000 to hire a new employee—not including salary or benefits! So keep that in mind if you choose to hire internally.

2. Work With A 1099 Freelancer With A Job Posting

You could also bring on a freelancer via a platform like Upwork.

Freelancers keep your org chart elastic. Meaning you have the flexibility to contract or expand depending on cash flow.

Note a few things with freelancers, though.

Hiring freelancers for long-term ongoing work isn’t compliant, and can land you in hot water. Misclassification of workers is a serious issue to the IRS. And if you’re caught in an audit doing so, even accidentally, the financial repercussions are serious.

Next, while you can part ways with them when you need to, they can do the same to you. Depending on your agreement, freelancers can fall through when you need them most. Don’t forget, they’re running a business of their own and have to make tough decisions just like you do.

Last, you’ll still need to dedicate some time to recruiting. To find an executive assistant that you click with, and is available for the hours you need, is a real feat.

3. Skip The Job Description, Subscribe To Your Next Remote Executive Assistant With Subscription Staffing

There are a number of remote executive assistant services out there, however, much like virtual assistant companies and freelancers, you’re still on the hook for compliance issues.

But in-between the flexibility of a freelancer and the security of a W2 employee is a new way to find a rockstar remote EA: subscription staffing.

A subscription staffing firm allows business owners and executives to subscribe to experienced remote executive assistants compliantly, fractionally, and flexibly (and for less cost).

This movement, pioneered by Boldly, is a game-changer for business owners and executives.

You want a skilled, experienced, personable EA without digging through resumés, interviewing dozens of people, and hiring (only to find out it’s a poor fit).

The good news? Boldly’s remote executive assistants have 10-15+ years of experience, many with Fortune 500 companies.

Subscription staffing also saves on the cost of finding and hiring someone on your own, especially when referencing the complexities of compliance for remote hiring.

Here’s how it works:

  • Fast match: Executives and business owners (subscribers) get fast matching to talented, guaranteed remote executive assistants without recruitment. (The process is normally 2-3 weeks.)
  • Simple subscribe: Subscribers pay a single monthly payment without the burden of payroll, contracts, and other legal issues
  • Smart scaling: Subscribers gain flexibility and scalability to work with someone (or multiple people) on a fractional basis—for the exact amount of time you need each month.

Subscription staffing offers the best of both worlds: flexibility and security.

Even better, with Boldly’s premium subscription staffing model, your EA will receive benefits, an incredible company culture, professional development, and stability — all of which add up to a long-term, winning recipe for a thriving partnership.

When Is The Best Time To Hire For Remote Executive Assistant Positions?

Whether your company is playing offense or defense, a remote executive assistant is an unquestionable asset.

The right person means it’s always the right time.

Subscription staffing lowers your payroll risk, with just a simple, predictable monthly subscription. And you could probably pencil out how much money you’ll save in a single month on the back of a napkin.

2024 is the perfect climate to streamline your work, get more efficient, and increase your productivity for every business.

Leaders with rockstar EAs have a real competitive advantage. They’re free to focus on strategic priorities, new revenue sources, and building a better company.

Talk with us today to see if premium subscription staffing is a fit for your team.
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.

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