9 Questions to Ask Yourself Before Hiring a Virtual Assistant

By Bill Peatman | Updated: 28 Mar, 2023

The virtual assistant (VA) market has grown substantially since the world went all-remote in 2020. Executives without offices still needed support, and the newfound openness to remote work made VAs an attractive option for anyone. From small business owners to executives at enterprise companies have found success offloading their admin work to a virtual assistant.

If you're realizing your need for remote admin help, you're probably searching for your next assistant.

There are dozens of options when it comes to hiring a VA. Before reaching out to a freelancer or virtual assistant service, you need to ask yourself a few key questions that will make your decision and the relationship successful.

1. What 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 a 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.

2. How 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.

3. Who Manages The VA?

Virtual assistants save you time by taking over admin tasks like scheduling, expenses, travel plans, data entry, and other important but time-consuming and repetitive tasks. But they will need training and performance management on your systems

Do you want to manage another employee? With freelancers and virtual assistant agencies, you're responsible for managing the VAs. Managed services take that burden off of your plate.

With a managed service, you get a dedicated account manager responsible for learning how you work and training and managing the VA to meet your needs.

4. How Much Time Do You Need?

Most virtual assistants charge by the hour, and few executives need 40 hours per week of support. That said, most require a minimum monthly or weekly allocation of hours.

How much time do you need?

The fact is, most executives don't know how much time they spend on admin work because they multitask all day and don't track their time. It can be helpful to document the processes you want to offload before interviewing VAs.

This will give you a good idea of the number of hours you will need and help you qualify candidates, ensuring they have the skills and experience for those documented tasks. It's also important to know how many other clients a VA may have and how much time and attention they can reserve for you.

5. Do You Have a Backup Plan?

Another thing to think about when engaging a virtual assistant is what happens if he or she is sick, on vacation, or leaves for another position. Few independent contractors or VA agencies offer backup VAs, while this is a standard best practice for managed virtual assistant services.

The backup VAs should be fully trained on your tasks and processes so that they can step in at a moment's notice without any lift on your part.

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 backup assistants that can step in if your primary assistant is sick, on vacation, or moves on.

6. What About Security?

Remote workers have become a target of hackers, as home networks and computers lack businesses-grade security protocols. If a VA uses a personal computer to access your systems, you need to have security standards to protect your network and data from any malicious attack.

Independent contractors and freelancers typically don’t have business-grade security systems. 

If you give someone access to systems like accounting, CRM, expense accounts, and credit card information, the stakes can be high. There's also the issue of the VAs themselves—do they observe best practices for security, and are they trustworthy?

Some services offer background checks, only allow VAs to have encrypted passwords (they never see your actual credentials), and can remotely revoke access if suspicious behavior is suspected.

Related Reading: What to Know About Virtual Assistant Security Risks

7. Can You Scale?

If your business is growing, and virtual assistants become a lifesaver, how do you develop that service within your organization? It can take as much as 40 days to recruit, interview, and hire a new employee, and as the number of VAs grows, management can become burdensome.

Companies in this position often turn to agencies and managed service providers as a more scalable means of hiring and managing VAs. A service provider will get to know your business and processes over time and find suitable VAs to join your team more quickly.

8. What About Pricing? 

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 

Related Reading: How Much Does Hiring a Virtual Assistant Cost?

9. What are Your Retention Rates?

This question is more for the virtual assistant agency but is important to ask. It has to do with the quality of the service the provider delivers 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.  

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.

Additional Reading