Even the best companies underestimate how hard it is to hire great executive assistants. Finding someone who’s both an exceptional executive assistant and an experienced remote professional is one of the toughest hiring challenges there is.
At Boldly, we’ve spent more than a decade building a team of remote executive assistants, and we’ve seen firsthand how quickly in-house hiring efforts go off course.
Finding the right executive assistant takes one set of skills.
Finding the right remote worker requires a completely different skill set.
When you need both? You’re dealing with a rare combination of expertise that’s difficult to master.
Let’s unpack why, and what you can do to get it right.
The Perfect Storm
87% of job seekers want remote work, with nearly a third only looking for remote jobs.
Companies know they need to offer remote positions to attract talent, but many don’t know how to hire remote team members well. And this is especially true for complex roles like executive assistants.
Executive assistants aren’t like other roles. You can’t just give them a test like you would with a programmer or measure them by numbers like a salesperson.
EAs need to understand the company dynamics, juggle complex schedules, and become an extension of their executive.
Read more: Working As A High-End Executive Assistant Isn’t Rocket Science (But It’s Close)
These are hard enough skills to evaluate in person. Now try evaluating these subtle skills through a computer screen, across time zones, without the body language cues that help you judge someone. Many companies end up using their traditional hiring playbook for a completely new game.
That’s when good companies make expensive mistakes, not because they’re bad at hiring, but because remote EA hiring requires specialized skills they’ve never needed before.
Why Normal Hiring Doesn’t Work
In-house hiring requires certain things like:
- Meeting people face-to-face
- Checking references from bosses who worked in the same building
- Training new hires in person.
Take these away, and the whole system falls apart.
For example, think about trust. In an office, trust builds naturally through small moments like chatting before meetings and watching people work well in-office.
Remote EA relationships don’t have the same trust-building moments. You’re asking executives to share things like email passwords, bank information, and personal details with someone they’ve only seen on a screen. Without a way to test trust remotely, companies either play it too safe (and miss great people) or take too many risks (and make expensive mistakes).
It gets harder when you’re hiring more than one EA. Managing several remote EAs brings problems with dividing tasks, communication mix-ups, and keeping everyone working the same way across different time zones. Without systems built solely for remote teams, what should be more help becomes more mess.
The Hidden Costs Nobody Counts
When an EA doesn’t work out, it costs more than just hiring fees. In fact, poor hires can cost 30% of their annual pay!
But here’s what most people do: they lose faith in remote work itself.
One bad remote EA often makes executives think “remote work doesn’t work.” This means they close themselves off from great workers around the world. They go back to only hiring locally, making their talent shortage worse.
What Makes the Difference?
Companies that succeed at hiring remote EAs don’t just have good HR teams; they’re experts in three key areas:
- Testing Remote Skills: They know how to check if someone can manage themselves, communicate online, and has succeeded working remotely before. They understand that a great office EA might fail remotely, while someone with remote experience brings valuable skills that normal interviews can miss.
- Building Trust Online: They’ve created ways to judge if someone is trustworthy through video calls. This means having a system for checking references, backgrounds, and asking the right questions for remote work.
- Managing Remote Teams: When hiring multiple EAs, they understand the special challenges of remote work like different time zones, different working styles, no in-office conversation, and more.
At Boldly, our employees stay more than twice as long as the industry average, which is typically two to five years. This isn’t because we pay more than everyone else. It’s because we know how to find, test, and match remote EAs in ways that work for everyone.
Learning From Experience
Many companies come to Boldly after trying other approaches first:
- They’ve worked with freelancers
- Tried lower-priced services
- Hired contractors
In the end, they’ve generally faced high turnover. inconsistent quality, and compliance red-flags.
One multinational name-brand fast food chain came to Boldly with a specific problem: they’d been using 1099 contractors but company policy meant they could only keep them for about a year. And it typically took four months for someone to learn the job and understand how their team and executives worked.
This meant just as the EA was hitting their stride, the company had to start looking for a replacement. It was an exhausting cycle that never allowed for real productivity gains.
Others have tried services that promise cheap, quick solutions. But as one client told us, “We tried a lower-priced service first, but the quality just wasn’t there. The turnover was constant—both in the assistants and in their client base. We spent more time training new people than getting work done.”
When You Get It Right
When remote EA hiring works, you create new possibilities. Execs get back 10-15 hours every week. Teams work better across time zones, turning a problem into an advantage. And you can hire talent they could never find locally.
Here’s the interesting part: because hiring remote EAs is so hard, getting it right gives you a huge advantage over competitors.
The Answer Isn’t What You Think
Most companies struggling with remote EA hiring think they need to get better at it themselves. They buy new HR software, send their teams to training, and keep trying new things. Sometimes this works, but usually it’s like asking your IT team to also handle sales calls (possible, but not efficient).
The better approach accepts that experts exist for a reason. You don’t do your own legal work or run your own data centers. So why believe that combining two types of hiring expertise (EA hiring and remote hiring) is something you should do yourself
Hiring a great remote executive assistant isn’t about trying harder. It’s about knowing what kind of expertise it takes.
Companies that recognize this don’t just hire better, they operate better. And that’s what we’ve spent more than a decade perfecting at Boldly.
Looking Ahead
Remote work isn’t going away. If anything, finding remote talent is getting harder. Companies that can’t hire and keep remote EAs will fall behind, stuck with only local candidates while their competitors hire globally.
Once you accept that hiring EAs and hiring remote are both specialties, you can make smart choices. Whether you spend years building this skill yourself or work with experts who already have it, the key is knowing that your normal hiring methods won’t work here.
Every system we’ve built at Boldly proves one thing: when you combine EA expertise with remote hiring skills, great things happen. Executives get the help they need, EAs find fulfilling careers, and leaders trade busywork for productivity.
The question isn’t whether you need remote EA talent (because in today’s world, you probably do!). The question is whether you’re willing to seek expert help. In the end, successful companies won’t be the ones trying to do everything themselves, but those smart enough to know when they need an expert to lend a helping hand.
Want to learn how expert remote EA hiring can help your executives do more?
Boldly has been perfecting this for over ten years, keeping workers twice as long as others in our industry. Let’s start a conversation to see how we can help.
