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10 Things I Wish I Knew Before Hiring A Remote Executive Assistant

Imagine you’re on the other side of hiring a remote executive assistant. It’s over. You hired someone. While we don’t know the path you took to get where you are, it may have been like many others. Trial and error, over and over.

Let’s say you’ve come up with a list of things you wished you could tell yourself before you began the process; things that would shave off a significant amount of that trial and error. 

This is that list.

1. My time has actual value.

If you’re focusing on tangible value, it’s easy to justify holding off on the expense of getting an executive assistant.

Problem is, you’re not considering the value of your own time in that equation. You don’t realize how much not having an executive assistant is actually costing you.

When you start putting dollar amounts on your time and calculate the value of your time, you’ll realize you’re paying yourself an awful lot of money to answer emails and book airline reservations. That’s not even counting how much lost opportunity costs you as you focus on admin tasks when you should be directing your energy towards growth and clients.

So, because your time has value…

Read more: How Much Does An Executive Assistant Cost?

2. I should’ve done this yesterday.

By the time you’re feeling the urgency to hire an executive assistant, you are probably long past the point of needing one. High-functioning business owners and executives like yourself have the ability (or a curse?) to enlarge an already full plate, squeezing in more work for yourself.

You’ve been your own executive assistant for a while now, doing all the work an EA should’ve been doing. How do you like having two jobs for the price of one?

“That’s not me,” you might tell yourself.

If any of these phrases have entered your mind or escaped your lips, that’s exactly the position you’re in:

  • I’ll put in some extra hours.
  • I wear many different hats.
  • I’ll see/do something with my family on the weekend.
  • I’ll work at home after everyone is in bed.
  • I’ll sleep when I’m dead.
  • I don’t have time for time off.

Here’s a hint: if people are recommending someone as an executive assistant for you, that’s a sign they’re recognizing you need help, even if you aren’t able to see it.

3. Hiring isn’t easy.

Bringing on a new W2 employee isn’t easy, and it certainly has a price tag. Consider that it takes about three months to hire a new employee, at a cost of about $4K.

Hiring comes with a lot of built-in how to:

How to write the best job description. How to source good candidates. How to interview. How to know what traits to look for. How to onboard. How to keep someone hired for more than five months. How to budget for payroll and benefits for new employees.

Let’s not forget that if your virtual executive assistant works in a city, state, or country different from you, you’ll need to make sure you’re following the employment laws of their location, including being registered to do business there.

Hiring isn’t a picnic, and because of that, you might have considered a different route: independent contractors.

4. Independent contractors aren’t the solution.

Bypass the hassle of a W2 employee, and go with a 1099 contractor. Easy solution, right?

You skipped the hiring, sure, but now your feet are firmly planted in compliance concerns. Misclassifying employees is common, and can also be costly. State and federal laws carefully define what an independent contractor is; get it wrong, and you’ll be paying fines.

There’s also the little issue of consistency, particularly if you use more than one independent contractor. Because you’re not allowed to control how your remote independent contractor does her job, and you have limits on how you structure the relationship, availability and how work is done may affect end-product consistency.

That consistency affects you as well as your clients. 

The lack of control over how work is done also reduces how much you can rely on an independent contractor, making them less of an asset in a priority position—like that of an executive assistant—where you need to offload significant tasks to make it worthwhile.

5. Diving into a pool solution isn’t great, either.

No hiring. No independent contractors. A staffing agency is where it’s at, right?

Well, possibly (see #6). But not all staffing agencies are created equal.

Some assign you the next available person in a pool. Every time you need work done, you come to them with a list and a different person does it. Work gets done, yes, but you still have to plan, provide, and manage it. The end results are as different as the person doing the work.

That’s not exactly the quality of executive assistant you need.

As remote work exploded into normalcy from 2 onward, there was no shortage of staffing agencies brimming with available help. But you’re not just looking for general help. You want an executive assistant, not someone to simply check off a to-do list. That means you need to have high expectations from a remote staffing agency, not just find warm bodies to fill chairs.

You have to determine if a staffing agency is right for you. What’s the talent and experience level of their team members? Do they work remotely? Do they have other jobs on the side? Will you have a dedicated worker or a pool worker?

A mediocre solution is no solution at all if it ends up creating problems later.

6. I don’t actually have to hire anyone at all.

You could’ve skipped the hiring headache and gotten a great remote executive assistant a different way. Simply put, let us do it for you.

We understand the frustrations of hiring or trying to find the right staffing agency, and that’s why we use the subscription staffing model. We do the hiring; all of our team members are our own W2 employees. That removes all of the compliance and legal issues from your shoulders.

Instead of three months and lots of effort, you can get a new dedicated non-pool executive assistant within a few days.

No payroll. No contracts. No compliance concerns. No filing. Ho hiring.


Not having to hire during a labor shortage where competition is fierce? Not having to gamble on a staffing agency and hope for the best? That’s priceless.

7. Yes, an executive assistant is within my budget.

Hiring is expensive, but staffing agencies come with expensive contracts, don’t they? 

It’s easy to slide back into thinking you can’t afford an executive assistant (see #1). We get that. We think having an amazing assistant should be open to everyone, and that’s why we use subscription staffing.

Subscription staffing is where you only pay for what you need. You pay a monthly subscription, and if you need to change your hours from month to month, what you pay reflects that. You’re not locked into a contract where you pay for a set amount of hours and instead, have great flexibility in how you manage your business.

Bottom line: any budget can handle subscription staffing.

8. I only want the best.

What do you want from your executive assistant?

Dream big, when you make that list. Here’s a few ideas:

  • Positive work culture, even with your virtual team or remote EA 
  • Increased productivity 
  • Constant goal creation, and taking the steps to meet those goals 
  • Attracting the best people, both for your team and as clients 
  • Long-term working relationships 
  • Someone you can trust to be honest and ethical and do great work, reflecting you well to your clients and other team members 
  • Someone who knows what you need done without you even having to ask 
  • Someone who cares as much as you do

Acknowledge you want the best and don’t settle for less.

“Yes, I want the best,” you might think. But then a little nagging thought pops into your head. “Do I even have a shot at accessing the best?”

9. The best talent is within my reach.

At Boldly, we get thousands of applications, and from all of them we only choose a few.

The very best, in fact.

We hire people who are extremely skilled and experienced, many with Fortune-500 and C-suite experience. We make sure they are highly motivated, self-starters, dedicated, and ethical.

That’s not something you could do easily on your own, but because we’ve done it, you have access to people of that caliber. When you come to us, you tap into the best executive assistants available.

We also work hard at creating a supportive team culture so that our people stick with us and, in return, with you. We have some team members who have worked more than eight years with us, an almost unheard of data point in the staffing industry!

Great talent sticks around other great talent, building on each other.

10. I have to take the leap, and trust.

The best tool in the world doesn’t do much if you don’t use it properly.

The same can be said about an executive assistant. If you don’t learn to trust them, they’ll never be as useful to you as they could be. 

Getting started with a new EA can be challenging, especially if you’ve never had one before, or if you struggle with micromanaging or trusting others. When it works well, you connect. You work as a team, as one unit, in forward motion. 

Unfortunately, it doesn’t always work that way when a staffing agency simply assigns you someone and sends you on your way.

We know you have to be a good match with your executive assistant if the relationship is going to work. When you contact us, we find out more about you. We dig into your work preferences, your personality, and the kind of work you do. We listen to you tell us what you want. And then we find you an executive assistant that’s a good match.

We believe in the idea that you can only move at the speed of trust. If your executive assistant is a good fit for how you work, you’ll be able to trust them more quickly. Both of you will understand how the other thinks. It won’t be so scary to hand over the admin work, because you recognize yourself in how they work.

Trust is the cornerstone of all of it. 

You trust us to hire the very best people and to create a system that makes it easy for you to access them as needed as your business grows and changes. 

And now that you know the ten things you wished you knew…there’s nothing stopping you from contacting us today. You’re one short conversation away from a great executive assistant and shifting your business into high gear.

Topic: Remote Executive Assistant

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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