Interviewing a Virtual Assistant (VA) can be an intimidating task.  Part of the initial interview process is ensuring the VA is competent in the skills you’re looking for. Beyond that, you also want to get a feel for how they communicate with you.  

A few things to keep in the back of you mind as you go through the interview process:

  • How good is their spoken English skills? (Especially important if you’re hiring for Customer Support)
  • Is there an ease in communication?
  • Do they respond eagerly to questions or is their attitude bland and seemingly uninterested? If it seems uninterested, is it because they are having a hard time keeping up with what you’re saying? Or do they just seem uninterested in working?
  • Are they asking you questions for clarity and to learn more about what you’re looking for?

A big part of hiring involves going with your gut feeling, which might be frustrating if you’re used to having tangible data points.  Our goal with this article is to help you with a series of questions that will give you those data points.

Here’s a list of our top interview questions to help you quickly and confidently judge if the VA candidate is a good fit for you and your team. Whether you hire a Virtual Assistant from us or independently, these questions can help you hone in on the right person for your team. 

Top 13 Questions for a Virtual Assistant


1. How did you become a Virtual Assistant (VA)? What’s your story?

This is a great opening question and provides an opportunity for the VA to talk about themselves. Does the VA feel comfortable with such an open-ended question or do they get really nervous? The ability to sell yourself and explain your past is a great way to judge someone’s confidence.

2. What are your core skills? Tell me about your experience helping a client with similar business needs.

Another opened-ended ice breaking question. This offers the VA an opportunity to tell you, specifically, about one of their strengths. If you found your VA through Liberty Virtual Assistants, then the answer to this question should be very closely related to one of your tasks. This shows the VA has been through in understanding what you’re looking for before your initial interview.

3. If I asked you to perform a task, and after accepting it you realized you couldn’t do it on your own, what would you do?

VA’s take on tasks that they aren’t 100% confident in for two reasons:

1) Because they enjoy the challenge.

2) They don’t want to seem incapable.

Do they answer this question with “Well, I think I would…” which shows that they might not have thought about it before. Or do they answer with  “This has happened to me before. I first went to Google/YouTube to try and quickly learn and if that doesn’t work, I would contact you for assistance and clarification”.

See the difference?  The first answer might indicate your VA could get overwhelmed by accepting tasks that might be over their head. 

4. Do you currently have another client?  If so, how many hours do you work each week? What time zone are you in and what hours are you available?

Here we are trying to gauge their FOCUS and COMMITMENT. If you plan to hire your VA for 4 or less hours/week, then it’s not uncommon for them to have another client. It’s important for you to establish and confirm the work schedule and then make sure your VA can commit and set aside focused time for your business.

5. How long were you with your previous client and why did you leave?

Online and digital work moves fast. Understanding why a VA’s last job ended (and how long it lasted) can give you a good idea of their commitment level.  

6. Have you worked in a call center industry?

This question is important if you’re hiring for Customer Service. The idea here is to gauge their experience. In our opinion, customer service is a fundamental skill that is hard to teach, but easy to learn if the experience is there. Call centers teach these skills to many VAs and you might be able to benefit from it.

If you’re looking for a customer service virtual assistant, let’s talk! We might have a solution for your business whether you’re looking for one person or a team. 

7. What is your least favorite task and why? Would you be OK with this type of task if it wasn’t regular?

Nobody likes to work on things which they aren’t good at or don’t like to do. Respecting that, or at least understanding it will help the VA feel like a valued part of your team.

Example: Maybe the VA says they really dislike transcription, but you really need them to transcribe a podcast one week. Communicating that this isn’t a common task will build that team mentality.

8. Are you married and do you have kids?

I’ve found that if the VA is married and with kids, they are typically more responsible, more dedicated, have more expenses and are more dependable. This is kind of a wildcard question, but from my experience it makes a difference. 

Questions like this also add a level of personable conversation in the interview. The goal is that you’ll have a healthy working relationship with this person. The ice-breaking questions that aren’t strictly business can help you gage their personality outside of work topics. 

9. Do you have backup internet?

The internet in any developing country has room to be improved. If their internet goes out, can the VA tether from their phone or visit a near-by coffee shop? 

10. What tools do you use every week to stay productive? What are some of your favorites?

Find out how the VA stays on top of their work and keeps things efficient. I use ShortKeys, Snagit, Google Calendar extension, Boomerang (for Gmail), Lastpass, Zoom, Slack and Telegram.

11. What CRM and/or Email Ticketing system(s) have you used?

Does the VA have experience keeping a database of clients and emails organized? We use Zoho CRM and Zoho Desk to manage our leads, contacts, accounts and support email tickets. This type of knowledge can really speed up the training period and get your business really organized.

12. What calendar software do you use (Google Cal, Apple iCal, etc)?

Using a calendar software means that you are organized. I create a Google Suites Gmail account for each of my staff and import their calendars so that I have visibility. Asana lets you connect the Google calendar and populates it with the tasks due on certain days. Also, I add all meetings and project milestones to my staff’s calendar.  

13. What project management tools have you used? What was your experience with them?

A project management tool, like Basecamp, Asana, or Trello, are at the heart of your company. They keep you organized and help your team understand their tasks at hand and due dates. Go ahead and get on the same page here. Even if you’re just using a personal Google Doc system to keep organized, having confidence in your VA’s ablity to plug into systems you already have is important. 


We hope you’ve found this helpful! If you’re looking for a Virtual Assistant, feel free to contact us:  We do a lot of the leg work in screening VAs for you so that once you reach the initial interview stage, you can focus on seeing who you work best with. We’d love to help with your remote staffing needs!  And as always – tweet us or email anytime for anything #RemoteWork related! 🙂


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