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10 Interview Questions for Virtual Assistants

When hiring remote workers, it’s crucial to ask specific questions to determine if the candidate has the necessary skills, experience, and work ethic. Key questions include time management, remote work experience, and communication skills to ensure the right fit for your remote team.

Dan Trujillo

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Common Interview Questions to Ask A Potential Virtual Assistant

Interviewing a prospective employee is always a sensitive task. The right questions must be asked, but equally important is understanding what the right answers are. Never is this more true than when interviewing a virtual assistant for your business. The following is our guide to interview questions for a virtual assistant. Because there are more layers to consider when hiring a VA, it’s imperative to cover all of your bases when interviewing your remote working candidate. That’s why we’ve compiled the top ten interview questions you should be asking any virtual assistant, along with what types of answers and skills to look for.

10 Interview Questions to Ask a Virtual Assistant

1. Tell me about yourself.

While not technically a question, this is always a great icebreaker to start with. There isn’t a right or wrong answer here, but you should pay attention to their confidence in sharing something personal about themselves. Take note of the aspects of themselves that they choose to highlight, be they professional or personal. This helps to determine how much of a culture fit they might be.

2. What’s your greatest strength as a VA?

Everyone has something that they know is their strength. This question should find out what that is, at least in their eyes. If math and numbers in general are their strength, then they’re likely an excellent fit for that accounting position you’re hiring for. If they mention their people skills and customer service experience, they may not be relevant to your non-customer-facing role.

3. What’s your greatest weakness as a VA?

This is a tough question for most, as interviewees don’t want to highlight anything bad about themselves. But it’s an excellent opportunity to gauge their confidence and self-awareness. A very personable professional should know exactly where they have room for improvement, and thus prepare you for potential speed bumps with them.

4. What are your areas of expertise?

This is different from their greatest strength, and an experienced professional should have a completely different answer for the two questions. Their answer should be more focused on things like job-specific duties, or experience in specific markets/industries. For example, being very knowledgeable in the world of real estate or technology.

5. What are some of your favorite tools, as a VA?

This is an excellent question because it helps identify their familiarity with the tools necessary for the position. As a bonus, it may also introduce you to beneficial tools you were unaware of. Their answer should include common tools/applications used for the position you’re hiring for. You need to know from the start what they’ll need training on and how much time to expect training them on it.

6. What do you do first if you receive a task you’re unsure about?

This is a great problem-solving question because it is so open-ended. Use this opportunity to gain insight into their thought process. What do they do first? Do they seek help or aim to solve it themselves? Did the question fluster them or did they have an answer ready? You can inject follow-up questions here, to continue the conversation and test their process against your own systems and processes.

7. What do you do when your computer or internet is unavailable?

This is a very straightforward and important question when interviewing someone for a remote position. Having access to a reliable PC and fast internet is crucial to staying on top of job duties, so it’s important to have alternatives available in the event of any issues. Most VAs will have a backup laptop or at least a phone/tablet they can use to work on in the meantime, even backup internet in the form of WiFi or mobile data.

8. What do you think is the most important skill for virtual assistants?

This is a good question to ask because it helps check how you both align, professionally. It also can demonstrate the interviewee’s knowledge of the position and the company itself. They are likely to answer with a skill they’re personally well versed in, so if the answer seems redundant don’t hesitate to dig a bit deeper. Ask for the reasoning behind their answer, and maybe even what they consider the second most important skill.

9. How many clients do you have right now?

Always an important question to ask, as you may feel more comfortable knowing their given assignments have their full attention. Many freelancers will juggle work for multiple clients since they are remote and unsupervised. While many can do this without issue, it really depends on the nature of the position you’re hiring them for. Less risk of overlap between companies with tasks that contain sensitive information is best.

10. Have you ever disagreed with a coworker? If so, how did you handle it?

This is a classic question that always presents the interviewee with a challenge. Most won’t want to admit to ever having a disagreement with a peer because they think it’ll reflect badly on them. But truly experienced professionals understand that disagreements are inevitable. What’s more important than avoiding disagreements, is how you handle them. Look for humility in this answer. This can be an opportunity for them to show vulnerability, as well as their capacity for difficult communication and following proper protocol.

3 Skills to Look For in a Virtual Assistant

Hiring a virtual assistant comes with a set of different expectations, on top of what you’d typically expect from a traditional hire. We’ve published guides on how to hire a VA, which go into great detail about the entire process. Below are just three of the top skills to look for, when interviewing a VA.

1. Strong Time Management

A virtual assistant is not tethered to the constraints often experienced by in-house employees. It can be easy to lose track of time or incorrectly gauge the time needed for a project when you’re working at home. This skill is very important for VAs. They need to be able to assess a project and know how long it will take them to complete it, and allocate the time among any other tasks accordingly.

2. Interpersonal and Communication Skills

Just because your virtual assistant is not at the office does not mean they aren’t a part of your team. Depending on the role, your VA will likely need to interact with not just you but other members of your team, frequently. It’s important they be able to communicate clearly, respectfully, and professionally. Being confident enough to reach out to peers or managers for assistance, questions, or with updates is very important. The sweet spot is when your VA doesn’t feel like they’re far away but feels like any other member of your team.

3. Self Motivation

This skill goes hand-in-hand with time management. Being virtual means it can be easy to get distracted and veer off course. It can also be easy to put things off when you don’t have anyone looking over your shoulder to check on your productivity. A VA is often handed a task and expected to hit the ground running. So this is another top skill, as a strong VA needs to be able to stay focused and motivate themselves to stay on track. A minimal need for micromanaging is ideal when leveraging a remote working employee like a VA.


We hope this guide on proper interview questions for a virtual assistant helps you pick the perfect professional. When you go through a service provider like MyOutDesk, every professional we hire into our virtual assistant pool goes through a thorough interview process. In addition to all of the above questions, we also submit them to an FBI-grade background check. When a client is ready for us to present candidates, they have the opportunity to ask these questions and more, themselves, before selecting their virtual assistant. This process ensures that our clients are presented only with the best candidates that fee their needs, while also having the opportunity to evaluate them against their own expectations.

If you are at all interested in how a virtual assistant can be of value to your growing business, please click the link below to request a consultation. It’s a questions and answers conversation with zero obligation and no risk of unwanted calls or emails. Just an opportunity to understand what we do, what you need, and if the two can be mutually beneficial.

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Dan Trujillo

Dan Trujillo

Writer at MyOutDesk

Dan, based in Sacramento, California, has over 5 years of experience copywriting for the virtual assistant industry. He produces content for social media, blogs, case studies, and publications with MyOutDesk.

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