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Your 2021 Guide To Hiring The Perfect Remote Executive Assistant

Written by: Sandra Lewis

In 2020, the work world went remote. 

Like many around the globe, you and your entire team had little choice but to go virtual. Remote work wasn’t a new idea, but the scale at which the world had to embrace it was something new. Remote culture with its terms, tools, and quirks became part of normal business.

A year later, in 2021, you might find yourself thinking that you want to keep your company working remotely, at least some of the time.

It’s a great idea, but that means everything, especially how you hire, has to change.

You’re not just looking for an executive assistant, you’re looking for a remote executive assistant. You’re not just looking for someone with experience that fits the job description, but someone who can do it all remotely.

There’s a difference.

Working remotely and working in-person and doing it really well is not the same.

While businesses made it through a year of working remotely because they had no other choice, choosing to go the remote route means rethinking how you work and how you hire.

Going From An In-Person To A Remote Workplace

2020 forced you to transition from an in-person to a remote workplace quickly. A permanent move in that direction means tightening up some bolts on the structures you had to build in a hurry.

Revamp your policies.

Maybe you created some ad hoc policies for remote work just to make it through 2020.

If remote work is permanent, you’ll want to create airtight remote work policies on availability and productivity expectations, tools, data management and security, use of personal devices, and hiring policies. 

Choose the right tools.

The greatest remote executive assistant in the world can’t do their job if the tools are fighting against them.

We’re talking about communication, project management, productivity, and security tools that fit the way you’ll be working, protecting your data as well as enabling your team to get things done.

It’s true you might be using less-than-ideal tools leftover from 2020, but if those tools didn’t work, why stick with them? Last year was a great opportunity to learn what did and didn’t work. Everyone else was in the same boat then, but 2021 is the time to make needed changes.

Solidify your work culture.

If you want a great business, you have to build a great workplace culture. It’s all about happier employees who are more engaged and productive.

It’s hard enough to maintain a great workplace culture when everyone is working in-person. Now imagine if everyone is remote and never actually in an office. How do you do it?

  1. Create a virtual community. Think of all the community building that happens in person. Meals in the breakroom, talking in the hallway, holiday office parties…these create community. Now’s the time to be creative. Find a way to build community virtually, through fun quizzes, online games, prizes, or a virtual bulletin board or casual forum. Encourage camaraderie and conversation. Have virtual meetings and be sure to connect personally with your team instead of just staying project-minded.
  2. Fine-tune management styles. Managers of remote employees have to have a lot of trust. Micromanagement and hard-handed oversight will fail every time. You’ll have to change how you measure performance for remote workers.
  3. Plan for meeting sites if necessary. Some teams are remote 100% of the time, others aren’t. If you don’t have a brick-and-mortar location but still want to have in-person meetings occasionally, set up a meeting spot, and try to keep meetings on a regular schedule so people can plan ahead.

Hire for remote work.

The most important piece, when it comes to moving to a permanent remote team, is to change how you hire.

The trick to developing a virtual culture with a strong growth-oriented team is hiring the right way. You have to find people whose work styles and personalities function well in a remote team setting. 

This isn’t an easy change to make. 

We’re used to looking at a list of skills and experiences on a job application, none of which takes into account the unique challenges that come with working remotely. 

What To Look For When Hiring Remotely

An executive assistant is a high trust position. Now throw in the remote piece, and you’ll see how that trust is really put to the test. 

A remote executive assistant needs to be someone who is:

  1. Trustworthy. A remote executive assistant is going to be in your email, your books, communicating with clients, and managing a lot of moving pieces. This is a position that requires your complete trust. Look for someone with experience and excellent references.
  2. Self-motivated and organized. Remote workers won’t have managers prodding them to work. Great remote executive assistants should always seem one step ahead of you, instead of waiting for you to tell them what to do.
  3. Expert communicator. Excellent communication is one of the traits of a successful remote team. Are they able to explain themselves clearly and concisely through written and verbal communication?
  4. Competent. They must have the basic skills and experience to meet your expectations for the job. It’s not just about a list of software or skill sets, though. It’s also about being flexible and able to adjust to change or rush scenarios while working remotely.
  5. Experienced. We’re not just talking about work experience, but remote work experience specifically. Have they done remote work before? If not, you’ll be their trial run. Some of the best employees in the office setting struggle in a remote setting.

Not only do you need to transition the entire way your team will work, with related policies and workplace culture, but you have to change how you think about hiring. Plus, these traits aren’t always easy to pick up on when doing an interview, much less a virtual interview. 

The Simple Way To Hire A Remote Executive Assistant

Are you ready to create it all from scratch? An entire remote team, a remote culture, and a reboot of how you hire?

That’s no small thing.

You have to be prepared to invest a lot of time and money into the transition to remote. It’s a daunting prospect, and maybe enough to make you scrap the idea of going remote.

2020 gave the world a taste for working from home, and in the U.S. alone, 39% of workers are asking that they be allowed to continue to work remotely, or they will quit their job. There might be lots of applicants out there, but more and more they’re looking for remote work.

There’s an easier way to do it.

Boldly’s focus is to provide you with the best remote executive assistant available. 

We took care of recruiting and hiring, finding those Fortune-500 experienced people who have a proven track record working remotely. We made sure they have every single necessary characteristic that remote hires should have. 

We even took care of building a positive and encouraging culture for each of our employees. When you’re matched with someone who best fits your needs and work style, they’re already rooted in an empowering and encouraging work culture. Plus, since they’re our employees, we’ve got best practice policies already in place.

There’s no need for you to reinvent the wheel. Contact us today, and you can get started with your new executive assistant right away.

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.