10 Questions To Ask When Hiring A Virtual Assistant

March 20, 2024

Business Tips

Bringing on team members or hiring a contractor for your wedding business can be a vulnerable process, I totally get it. It is your baby, your lifeline and your business so you don’t give the responsibility to anyone lightly- and you shouldn’t! That is why I am sharing some helpful tips and my top questions to ask when hiring a virtual assistant.

If you are considering hiring a virtual assistant (VA) be sure to check out this blog with a list of some of the most popular things you could be outsourcing for your wedding business. Also, this blog on how a VA can help maximize the efficiency of your wedding business. The skill set and tasks that an outsourcer can help you with are truly endless. For simplicity’s sake, we are going to address hiring a VA to help with administrative tasks in this blog.

Questions To Ask When Hiring A Virtual Assistant

1. Do you have a contract length or minimum commitment? 

Some VAs work on a retainer basis with 3-month, 6-month+ contract minimums while others work on a month-to-month basis. Be sure to know what you are getting into before committing to anything.

2. What are your packages and hourly rates?

Some VAs work on an hourly rate basis, while others have hourly packages where you may get a certain number of hours for a discounted rate. Others may work on a task/ project/ duties basis, where certain tasks are included in their package. This is more common with social media, marketing, and other niche contractors..

3. What happens at the end of the month with any unused hours? Do they roll over to the next month or do I have to use them all during their allocated month?

If your contract terms state that unused hours do not roll over into the next month it is best to know what tasks you need help with in advance and get the full support of your VA.

4. How do you track your hours worked? 

Every VA has a different system on how they track their hours and how often they update you on the hours used. Find out which system your potential VA uses to ensure clear communication of the work done.

5. What experience do you have with the following software, tools & applications? 

Every VA has a unique set of skills and experience with different software. Be sure that your potential VA has experience working with the same software that you use and communicate with them if you are open to trying new software or want to stay on your existing applications.

6. How do you manage your client inboxes?

If you are hiring a virtual assitant to help you with your emails and inbox management, this is an important question to ask. Find out how often then check your inbox, how they file/organize items and set expectations of how you’d like them to respond (or not respond).

7. How do you prefer to communicate with your clients?

With the virtual nature of a VA job, you could be hiring a virtual assistant anywhere in the world. So, discuss with them how they communicate with their clients, as well as how often. Some prefer email only or use Slack or Voxer for direct messaging. If your VA is local, they may be open to text messaging, but not all open to this option.

8. What experience do you have in the wedding or event industry?

Experience in the wedding and event industry is an asset or a deal breaker for some businesses. However, depending on the tasks that will be assigned, it may not be necessary. If there is a lot of event lingo or unique event-specific tasks, it is best to get a good understanding of your potential VA’s past experience in the industry. 

9. Are you working with anyone in the same region as me or a direct competitor?

Don’t expect your potential VA to list the names of their clients but this is a helpful question to ask to see how familiar they are with your region and market. For administrative tasks, this should not be a deal breaker. However, for social media or more marketing or brand-related tasks, this is important to know as you want your business to stand out.

10. What does your onboarding process look like?

Every VA operates differently. Some may want to hop on an onboarding call while others may solely do everything via a questionnaire. Some require standard operating procedures (SOPs) first thing when starting out and some can help you build these. The smoothness of the onboarding process truly sets the tone for the rest of your working relationship.


  1. When do you have availability for your next start date?
  2. What timezone do you work in?
  3. What are your working hours?
  4. How much notice do you need if we want to terminate the contract?
  5. What is your payment system like? How often do you invoice, when do I receive my invoices, do you do payment plans?
  6. Do you have any testimonials you’d be willing to share?

As important as it is to ask the above questions during the interview process, it is also equally important to get a good understanding of your potential VA as a person. Nothing is worse than being just a number or an employee for a business. Show interest in who they are, their passions, skill sets, hobbies and lifestyle. Find out if they live in the same region as you, have similar interests or even have a family. This will help you not only be a better boss but also have a clearer understanding of who they are and why they behave the way they do. After all, we are all human and work is not the be-all end-all.

We hope you found the above questions helpful and wish you all the best during the interviewing process when hiring your virtual assistant!

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