The virtual assistant business was growing rapidly before Covid-19, and like other remote work-enabling businesses, it accelerated during the pandemic. There are lots of virtual assistant companies offering admins for hire, as well as freelancers working for themselves and getting business through platforms like Craigslist and Upwork. 

Why the boom? Without an office, just about every role is now remote, so the barrier of geography is less of a consideration when accessing help with everything from software development to executive admins. Also, virtual assistants can be hired on-demand for specific tasks and in an uncertain economy, the model offers a lot of flexibility for executives that need part-time support. 

There are basically three ways to engage a virtual assistant: 

  • Hire a freelancer. 
  • Hire a contractor through a virtual assistant agency. 
  • Use a managed service provider that hires virtual assistants and manages them for you. 

There are pros and cons to each model, and with each model, there is risk. Any hire, full or part-time, has financial and time-based risks. If you hire someone and they don’t work out, you’ve lost time and money.  

1What will they do?

This is really a question to ask yourself, but it’s important. Before engaging a virtual assistant freelancer or company, you should be clear on what you want the assistant to do. This may sound obvious, but you might be surprised how many entrepreneurs don’t really know how much time they spend on tasks, and how hard it is for them to get what’s in their head delegated to someone else. 

Be specific because lack of clarity can quickly lead to miscommunication and unmet expectations. Be specific about the tasks and outcomes you expect. Typical tasks virtual assistants do are: 

  • Scheduling meetings and calls 
  • Calendar management 
  • Email correspondence 
  • Light bookkeeping 
  • Sales follow-up 
  • Travel planning 
  • Expense accounts 
  • Invoicing and payment processing 

Note that some of these tasks involve contact with customers, which will mean you want a level of professionalism that matches your brand. Outcomes mean how much time you expect each task to take on a daily or weekly basis.

2How are they trained and onboarded?

Knowing if a virtual assistant is qualified and trained to do the work you need can be a challenge, especially with freelancers. There is no degree or credential to validate skills. You need to know: 

  • Do they have experience with your tools? 
  • Can they get up to speed on your processes?  
  • Can they help you get what’s in your head into theirs? 

With freelancers, you take their word for it. Maybe they have references. Some virtual assistant agencies are little more than matchmakers, handing you a stack of resumes to choose from, but they may have done some due diligence for you.

Managed service providers hire, train, and manage the virtual assistant providers and bear most of the risk for the quality of the service. The managers onboard the virtual assistant onto your tools prior to the engagement, so they show up ready to work on day one.

3Who manages them?

One thing clients don’t always think about in hiring a virtual assistant is the amount of management it will require. Are you looking for more people to manage? This is an important question as the reason you’re looking for a virtual assistant is to make your life easier.

You’re looking for someone you can trust to be your mini-me. You need to think about how much added management burden you want to bear. If you’re comfortable taking on new staff, a freelancer or agency might work if you find the right person.

A managed virtual assistant service provider, as the name implies, does the performance management on your behalf. You give feedback to the account manager, and the account manager coaches the virtual assistant behind the scenes. 

4What happens if they quit? 

The nature of part-time work is that the workers are often: 

  • Not always reliable. 
  • Always looking for better opportunities. 
  • Serving other clients that might be a higher priority. 

We’ve all heard of (or experienced) the disappearing freelancer or contractor. They vanish and take your time and money with them. The risk is especially high with freelancers. Agencies can have turnover too, and the contractors they hire may have clients through other agencies or work as freelancers on the side. Managed services, on the other hand, mitigate this risk. Managers document all processes and train back-up assistants that can step in if your primary assistant sick, on vacation, or moves on.

5What are their retention rates for assistants and clients?

The first four questions have to do with how the virtual assistant company or freelancer delivers their services. This question has to do with the quality of the service they deliver as well as the quality of the experience they provide for their virtual assistants.  

  • A high retention rate of clients is one of the strongest indicators available of the quality of service delivered. 
  • A high retention rate of virtual assistants speaks to the value the business offers its employees or contractors.  

High turnover rates are bad in basketball and bad in business. 

6What About Price?

The price of a virtual assistant usually boils down to an hourly rate. Like many services, you need to look beyond the number to the value you’ll get for what you pay for. For example, if one provider costs more but can take more off your plate, it might be worth the extra money. Also, you need to look at additional expenses you might incur such as: 

  • Computer 
  • Software 
  • Training 
  • Payroll taxes 
  • Your time training and managing

7What is your security policy?

In the age of cyberthreats, you also need to consider the security of a virtual assistant’s software and hardware. Independent contractors and freelancers typically don’t have business-grade security systems. Some businesses, like healthcare and financial services, have strict security requirements. There are three areas of security to address: 

  • Network security—is the assistant’s network secure? 
  • Device security—if you provide a company device or not, what happens if the computer is lost, or the assistant disappears? 
  • Human security—does the company or do you do background checks and have confidentiality agreements?

What Kind of Relationship Do You Want?

Ultimately how you engage a virtual assistant has a lot to do with the kind of relationship you want. Is it a short-term assignment for some not-so-important projects that you need to get done? Then a freelancer might be fine.

Are you looking for long-term help from someone who will add increasing value to your team?

You should look for a virtual assistant company that is aligned with that goal. Managed virtual assistant services are built to acquire and grow institutional knowledge about the businesses they serve, and to scale as needs and capabilities grow. 


How to Work With a Virtual Assistant