Virtual Assistants

Hiring an Executive Assistant: Strategies for Entrepreneurs to Boost Productivity Virtually

A lady in semi-formal professional attire at a computer desk in an office hiring an executive assistant.

Are you thinking of hiring an executive assistant for your business? 

In this article, we’ll help you understand the EA, benefits of hiring one, and what that entire process looks like. 

Understanding the Role of an Executive Assistant

Definition and key responsibilities

An executive assistant is someone who directly assists a company executive. Their responsibilities range from business tasks to duties related to an executive’s personal or home life. 

Similar to secretaries, a lot of their duties are administrative in nature. This includes travel and accommodation arrangement, scheduling, email management, reporting, and more. 

The difference between an executive assistant and other administrative roles

One key difference between an EA and other types of admin assistants is their managerial function. As the name suggests, EAs have some executive power. This means they have the authority to delegate, lead, and supervise tasks and teams in certain situations. 

The Benefits of Hiring a Virtual Executive Assistant

Cost-effectiveness and scalability

Having an in-house executive assistant does have its advantages, but virtual EAs are more flexible price-wise. Their rates are more adaptable in that you can hire them for specific tasks and then scale up only when needed.

Access to a global talent pool

When you hire locally, the fact of the matter is that you have limited options. You may have candidates with excellent resumes, but they may not be the right fit for your business. Global talent gives you a variety so you don’t settle.

Increased productivity and focus for entrepreneurs

There’s an opportunity cost when you aren’t spending time efficiently. Hiring an executive assistant means you can direct your time and efforts elsewhere. EAs also act as a second pair of hands that helps you complete more complicated tasks faster. While you write meeting agendas, an EA will set a meeting date where all needed parties are available. 

Identifying Your Needs

A man in a suit sitting at a table thinking.

Deciding between a full-time vs. part-time assistant

Hiring full-time makes sense if you have a lot of work you want to outsource. Part-time hiring can be more economical. For instance, you might hire for specific tasks or only during a specific time of day. Examine what makes more sense for your business needs and hire accordingly.

Skills and qualities to look for in a virtual executive assistant

An EAs main duties revolve around calendar management and scheduling, communications, logistics, management, and other admin tasks. 

As such, they must possess valuable skills such as:

  • Organizational skills
  • Time-management
  • Good oral and written communication 
  • Research skills
  • Multitasking
  • Management skills 

The Hiring Process

Where to find qualified candidates

There are multiple places you can find vettable candidates. There are agencies, freelance marketplaces, as well as social/business networking sites. Some of these include Upwork, FreeUp, LinkedIn, and other EA hiring sites. Whatever site you choose, make sure they have some kind of rating or review system. 

Crafting an effective job description

This is an important step when hiring an executive assistant. This helps you communicate the roles, responsibilities, and qualifications clearly. You create one using  an executive assistant job description template

Screening and interviewing candidates virtually

Before you conduct your remote interviews, we recommend creating a list of interview questions. It’s also important to choose your platform ahead of time. We personally recommend Slack for interviews. 

Conducting reference and background checks

Candidates will usually have references to their previous workplace on their resumes. You can also explicitly request this on your job post/job description. If hiring through agencies or freelance platforms, check reviews and ratings. 

Onboarding and Training

A man and woman doing onboarding and training with a laptop looking at something and smiling.

Setting up communication and task management tools

We always say the remote onboarding process is crucial. It is during this process that you can familiarize people with the tools and software you use. The sooner you introduce it to them, the more time they have to adapt to it. 

Establishing clear expectations and goals

This part of the process is also where you can reaffirm what this partnership entails. Here you set the mission, communicate the vision and establish objectives. This also helps set healthy work boundaries in place as well. 

Training on specific systems and processes

You should conduct any training regarding proprietary software, SOPs, and the like early on. This may involve giving them instructional material and assigning someone to coach them through. 

Building a strong working relationship remotely

Integrating remote hires into your teams and workflows is key to healthy partnerships. You can do this through temperature checks and regular team-building activities. A healthy work environment boosts morale, which in turn improves the quality of their work. 

Best Practices for Working with a Virtual Executive Assistant

Effective communication strategies

We already mentioned that you should establish communication channels early on. 

Also, ensure that you reply to messages as promptly as you expect them to answer yours. Both sides should model active listening.

Setting up regular check-ins and feedback chains

Scheduling regular update calls can have a few benefits. For one, you can check progress and maintain a level of supervisory control. Second, you can gain insight into the inner workings of the project.

You do this by giving your EA opportunities to ask questions, provide feedback, and bring up suggestions. This is a key part of their role, as they can observe things much closer than business executives. 

Leveraging technology for collaboration and productivity

Partnering with technology can improve efficiency by a significant margin. Think about team management software that allows for communication, real-time collaboration, and progress checking. Consider other technologies that include automation features where you can set rules that save you tons of time. 

Ensuring security and confidentiality in a virtual setup

There are two factors involved in security: the data itself and those handling the data.

Any business that has dealings online (which is most), should know the most secure channels for relaying information. Additionally, you should consider investing in data security software.

When hiring an executive assistant, make sure they sign a data privacy contract andthat you bring them up to speed on your data policies. As a rule of thumb, only share the most necessary information on a need to know basis.. 

Legal and Contractual Considerations

Some documents on a clipboard.

Understanding employment laws for virtual employees

Naturally, if you plan on hiring internationally, you should also acquaint yourself with any laws related to that decision. 

One benefit of hiring remote workers is that you have no obligation to provide typical employer benefits. This includes healthcare, retirement bonuses, etc. You also don’t typically have to fill out tax papers or documents from that country. 

Drafting a comprehensive contract

Contracts protect both parties from disputes, misunderstandings, and abuses. When drafting a freelance contract, you can use templates or start from scratch. Always include important information such as names, dates, deadlines, scope of work, deliverables, and rates. Be as detailed as possible. 

While a lawyer isn’t necessary, they can’t help cover all bases and prevent loopholes. 

Discussing and setting up payment arrangements

You’ll notice that most freelancers will come with a rate upfront. On marketplaces you can usually see a rate range next to their profiles. Payment negotiations also happen during the interview process when narrowing down candidates. 

Once finalized, your contract should also include your payment agreement with the EA. This includes payment amounts, terms, channels, and dates. 

Frequently Asked Questions

How do I ensure my virtual executive assistant stays motivated and engaged?

There are three things we recommend

  • Equip them thoroughly with the tools and information they need 
  • Regularly check-in with them and listen to their feedback and suggestions
  • Implement good suggestions and provide positive reassurance 

What are the common pitfalls in hiring a virtual executive assistant and how can I avoid them?

Most bad hires are usually the result of poor research or poor management. 

When hiring, choose from reputable marketplaces, agencies, etc. Make sure you set clear expectations in your job description and ask proper interview questions for executive assistants

How should I manage time zone differences with my virtual executive assistant?

Time zone differences can be troublesome, but you can also use it to your advantage. For instance, EAs can work during your off-hours, so progress is continual. 

Can a virtual executive assistant handle sensitive or confidential tasks?

Yes, it’s a given that those in this position handle information with some degree of confidentiality. Hiring someone you deem trustworthy may not be enough. You must also have data security contracts and SOPs in place before hiring. 

What are the key indicators of success when working with a virtual executive assistant?

  • You have more time to get more done. 
  • Your processes are getting more efficient. 
  • You’re more organized.

What Is Outsource School?

outsource school

Outsource School helps you to unlock the potential of virtual assistants and accelerate your business growth.

This is the exact system Outsource School’s founders, Nathan Hirsch and Connor Gillivan, used to go from zero to 8 figures and 40+ virtual assistants with an exit in 2019.

Since being founded in 2020, Outsource School has helped 1,000+ business owners hire 2,000+ virtual assistants for their companies.

Schedule a free sales call to learn more

Free resources you might like: 


That concludes our “hiring an executive assistant” crash course. Hopefully, you now have a better grasp of the EA role and how to hire and manage one effectively.

If you want to learn more or think we missed anything, we recommend checking out our other posts related to this topic.