Skip to content

Looking to hire
talented staff?

Get Started

Ready for the dream
job you never
thought existed?

Meet Boldly

The Surprising Bond You Build With Your Executive Assistant (And Why It Matters)

Remote work is about distance, and that makes it seem a bit cold and impersonal. 

There’s the idea that nothing beats the experience of being in-person. The socialization, the ability to pick up on non-verbal cues, and the general camaraderie that comes from being together with other people is hard to replicate virtually.

That means there’s a kind of expectation that virtual working relationships will be less rich than if they were in-person. Unfortunately, those lower expectations get carried into the mix and can color the success you have with your executive assistant.

We know this because many clients come to Boldly with this kind of assumption about their new virtual executive assistant. They expect talented people capable of great work, but that’s about it.

We love surprising them.

We know that you can create an incredible, connected, and long-term relationship with your executive assistant. And when you do, everything changes.

The Biggest Challenges With Virtual Teams

Let’s start with that baggage of low expectations.

If you don’t expect a connected long-term work relationship with your virtual executive assistant, you’ll get what you’re looking for. It’s true that virtual teams come with their own unique dynamics. No matter the industry, you have to approach your virtual hires as seriously as you would your in-person hires. 

With virtual teams…

  • Far away can mean feeling left out. If only some members of your team are virtual, they’ll probably feel left out. It’s not just that they miss out on being involved in person, but if they’re geographically distant, they aren’t even experiencing the same restaurants or social activities others are. 100% virtual teams fare better in this area.
  • Communication and trust are tough and scary. Executive assistant is one of those positions that require a high level of trust, not only for the type of access and information they work with, but also that you can relinquish the reins a bit. As you’ll see, trust is the foundation for real relationships.
  • Connected relationships don’t happen by default. Having a meaningful working relationship with your executive assistant won’t happen unless you’re purposeful about it. That starts with the hiring process. It’s almost impossible to fix an at-odds work relationship that was broken from the start. 
  • Clashing relationships wear everybody out. The goal of an executive assistant is to help you with your workload, not add to your stress. But if you’ve ever had to work closely with someone who doesn’t work like you do, think like you do, or appreciate what you’re trying to accomplish, you know how ugly that can get. 

All of these challenges lead to a lack of longevity, and that, in turn, exacerbates these challenges. That’s a kind of brutal Catch-22. It’s hard to seriously trust and rely on someone if you’re worried they’ll quit in a month. And it’s hard to stick around if you aren’t fully trusted.

Trust is the crucial hinge, and the reality for the remote work industry is that most executive assistants end up being short-term. When working relationships are off, productivity declines.

This is why we took a different path.

Creating A Long-Term Connection With Your Executive Assistant

Out of more than 32,000 applications a year, we pick our select team. That means we have stringent standards where only a few make it out of tens of thousands. Most of our team members have 10-15 years experience, many with Master’s degrees and all with incredible skills. This sets our executive assistants apart from others, and we could probably convince you of our ability to match for skill sets alone. 

But this is where we get to the important part of the conversation: you have to also match for personality. 

Why does that matter?

Because trust is the all-important factor, and people tend to trust what they recognize. 

There are long lists of how we can build and improve trust, but intuitively, without effort or will, we trust what we know. We like people who are like us, and we trust them more because of that. So while it’s important that we make sure your executive assistant has the skills and experience you need, it’s also important that we match your personalities.

A good match goes both ways. We make sure both you and your executive assistant get a chance to meet virtually, and that you both agree to the working partnership. In other words, you both choose. You both have to have a say if the match will work.

A good match means you recognize yourself in your executive assistant if you’re a good match. You’ll trust each other, because you both understand how the other thinks, and where they’re coming from. Your work styles will be similar because you’ll be motivated by similar values.

You’ll both enjoy working with each other, trust each other, and you’ll end up with a positive long-term working relationship.

We could wow you with more data, but let’s look at real life examples we’ve seen in action.

Creating Inevitable Growth

As founder and CEO of Eagle Academy, Fabian was trying to run everything himself. That’s a quick path to burnout, so he came to us looking for an executive assistant. We paired him with Pauline, who seemed to be the right personality fit as well as completely qualified for the work.

Right out of the gate, Fabian trusted Pauline to handle crucial parts of his business. From accounting to improving systems efficiency, she became a kind of cornerstone for operations.

Instead of burnout, Fabian discovered that he actually had time for a personal life in the evenings, and Pauline was thriving. He’d never have gotten there if he didn’t feel he could trust Pauline, and she’d never have excelled as she did if she didn’t feel trusted. They have been working together for nearly 6 years now.

A Perfect Match

Norma ran a successful nonprofit, but needed some help as the workload increased. She contacted Boldly, willing to give subscription staffing a try. We matched her with Kali, and the rest is history.

Kali was highly experienced and skilled, and it wasn’t long before Norma’s initial 15 hours a month had increased to 100, and her job went from basic admin to important organizational duties. But the real picture of success comes when you step back and realize how many years they’ve worked together.

For over four years, they’ve made it work. That’s a long time in the virtual staffing industry. Even better, though, is their great working relationship. They complement each other perfectly, with similar working styles, sense of humor, and most importantly, trust. 

Just like Pauline, Kali was highly skilled. But even more importantly, she was the best fit. In both cases, everyone thrived because there was a good match that led to a healthy, trusting work relationship.

When you come to us, we’ll absolutely find you the best set of skills and experience that your work requires. 

But we’re also going to make sure everyone agrees it’s a good fit. If you’re ready for the advantages that come from a great virtual working relationship, let us know. We know we have the perfect person just a few clicks away.

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.

You might also like

8 Execs Share Why A Premium Executive Assistant Was So Worth It

Move Your Business Forward

Should Your Executive Assistant Have Access To Your Email?

Remote Know-How
Remote Executive Assistant working at her desk

How To Hire A Rockstar Remote Executive Assistant In 2024

Remote Know-How