30 Best Virtual Assistant Interview Questions

Hiring the right virtual assistant can transform your business operations and boost your productivity - but finding the right fit starts with asking the right questions. In fact, 75% of employers say that the interview is the most critical part of the hiring process, according to a recent LinkedIn report.

At A Team Overseas, we have significant experience interviewing virtual assistants and ultimately onboarding them into different teams. So we made this comprehensive guide to help you identify top talent from understanding your needs to evaluating your candidate’s answers. We also compiled the 30 most essential virtual assistant interview questions to help you assess key qualities, from communication skills to technical proficiency, while setting clear objectives and structuring your interviews effectively.

Why Should You Hire A Virtual Assistant?

While not an interview question, it’s one thing that business owners should consider before starting the hiring process. Hiring a virtual assistant can be a game-changer, but having clarity on what you need help with and what you want to use them for helps you build a model of what the ideal VA can look like for you and thus narrow down the skills, qualities, and other basic requirements you are looking for.

Virtual assistants today can specialize in various tools, niches, and fields. They work remotely, providing support in areas like business administration, customer service, and social media management. This flexibility is invaluable, especially if you need help in multiple areas and looking to keep costs to a minimum without sacrificing operational efficiency.

Another significant advantage to hiring VAs is the subsequent increase in productivity. A report by McKinsey found that delegating routine work can increase productivity by up to 20%. Most virtual assistants handle routine tasks, but these professionals also bring specialized skills to the table. From social media management to customer service, you can find a virtual assistant with the expertise you need or at least with the willingness to learn and grow. You can always set stretch goals for them to help their role evolve naturally as they grow alongside your organization.

Three Pillars to Guide Your Interview Questions

Once you’ve identified what you want in your perfect VA, it’s time to consider your approach to interviewing them. A candidate may have the right set of technical skills and prior experience but you still need to make sure they will fit with your company culture. A thorough interview process isn't just about checking boxes—it's about finding someone who can truly transform your workflow and become an integral part of your team.

Before we explore specific questions, it's crucial to understand the three fundamental areas that will help you structure your interview strategy effectively.

• Professional Background Verification: A core part of the interview process is validating whether they have the right experience. Their prior experience provides valuable insights into how a VA might handle future challenges. You'll also want to verify not just their work experience or history, but also their track record of reliability and professional growth.
• Skills Assessment: What specific skills do they have? If, for example, you’re looking for someone with a project management background, does the candidate have prior experience? What specific tools do you currently use in your business? Knowing the tasks or projects that your virtual assistant might be helping with, what relevant tools should they be proficient in? Technical proficiency isn't just about knowing how to use specific software—it's about adapting to new tools and understanding how to leverage technology to improve efficiency. You'll want to assess both current capabilities and learning potential.
• Cultural Alignment: Working remotely requires strong alignment with your values and work style. Your VA should understand and embrace your company culture, even from afar. This alignment ensures smoother communication and better long-term collaboration.

30 Best Virtual Assistant Interview Questions

The following questions are strategically designed to uncover not just skills and experience, but also work style, problem-solving abilities, and cultural fit. Use these questions as a foundation for your interviews, and don't hesitate to follow up on any answers that need clarification. Remember, the best responses often come from candidates who provide specific examples from their past experiences.

Here are 30 key questions to help you identify good candidates for your specific needs:

General Background Questions

1. Can you tell me about your previous experience as a virtual assistant?
2. What types of organizations have you worked with in the past?
3. Why did you choose to become a remote executive assistant?
4. How do you stay organized while working remotely and across different time zones?
5. How would you describe your communication style? What are your preferred communication tools?

Individual Skills and Experience Questions

1. What specific tasks have you handled before as a virtual assistant?
2. How proficient are you with [specific software/tool relevant to your organization]?
3. Can you describe a time when you had to learn a new task/process quickly?
4. How do you manage multiple tasks with competing deadlines?
5. What is your approach to handling repetitive tasks?

Situational Questions

1. Describe a challenging project you managed and how you handled it.
2. How do you prioritize your tasks when everything feels urgent?
3. Can you give an example of how you handled a difficult client situation?
4. What steps do you take to ensure accuracy in your work?
5. Tell me about a past “win” you’ve had as a remote executive assistant.

Cultural Fit Questions

1. What types of projects are you most passionate about?
2. How do you ensure effective communication with your clients?
3. Describe your ideal working relationship with a client.
4. How do you stay motivated while working remotely?
5. What do you enjoy most about being a virtual assistant?

Role-Specific Questions

1. How would you go about doing research for a client?
2. How would you go about identifying and presenting pain points in your client’s calendar and inbox?
3. What is your process for learning each client’s specific preferences?
4. What steps do you take to ensure you provide the best client experience?
5. What steps do you take to ensure customer satisfaction?

Problem-Solving Questions

1. How do you handle unexpected issues or emergencies?
2. Can you describe a time when you had to solve a complex problem 100% on your own?
3. What is your approach to handling tasks you are unfamiliar with?
4. How do you ensure your work meets the client’s expectations?
5. What would you do if you missed a deadline?

Pro Tip: These questions should serve only as a starting point rather than a rigid checklist. The most valuable insights often come from follow-up questions that explore their responses in more detail. Also, pay particular attention to candidates who show genuine interest in your business and can relate their experiences to your specific needs. It’s a sign they might be a good culture fit.

Evaluating the Responses to These Virtual Assistant Interview Questions

Finally, the way you evaluate the responses to your virtual assistant interview questions can make or break how you go about hiring the right talent. As Charlie Munger says “Wisdom is prevention”, meaning you’ll be better off covering all the deeper-level bases when interviewing EA candidates. Make sure they don’t have any of your deal breakers and they’re excited about your mission, vision, and core values. To better evaluate this, you should focus on these key areas that will help guide better-informed hiring decisions:

1. Communication Skills: Communication is performance. Clear and effective communication during the interview is an insight into how they will communicate with you once you start working together. A CareerBuilder survey found that 75% of employers have hired candidates based on their professionalism during the interview process, and you should probably give equal relevance to this trait. Are they concise and to the point? Do they use professional language? Are they transparent enough? These are the questions you should be asking yourself when interviewing a virtual assistant.
2. Problem-Solving Abilities: If you want to ensure your future VA has the right resolution abilities, you should always assess how candidates handle problem-solving scenarios. Look for examples of their capability to think both critically and independently. Did they provide specific, detailed answers? Did they demonstrate a logical approach to resolving issues? Did they come up with a strong, individual answer or did they ask you a billion follow-up questions? Strong problem-solving skills indicate a candidate's capability to manage unexpected challenges more effectively, and will also affect how much of your workload they can transfer onto their plate. So make sure they’re a good fit here!
3. Cultural/Personal Compatibility: A good cultural fit leads to better overall performance, higher client/VA satisfaction, and a better chance of a long-term partnership. So it’s best to be particularly thorough about their responses to questions about motivation, ideal working relationships, openness to feedback, and work environment preferences. The goal is for you to work closely with each other, and for them to support you across different areas of your life, so you should truly get along if you want to work together at your fullest potential.
4. Technical Proficiency: According to a LinkedIn survey, 57% of senior leaders believe soft skills are more important than hard skills - with many considering this to be particularly true about virtual assistants - but a good level of technical proficiency is still crucial for specific tasks. As all VA roles are different by nature, it’ll be best to ensure the candidate has the necessary technical skills for the specific tasks you plan to delegate. You should assess their familiarity with the tools and software relevant to your business and ask follow-up questions to get a feel for their level of expertise.
5. Attention to Detail: Attention to detail is vital for tasks like data entry, scheduling, and customer service. Now, to ensure you hire an attentive VA, evaluate how candidates handle questions that require detailed responses. Do they provide thorough and well-structured answers? Are they meticulous in explaining their processes? What about their past experiences, do they explain previous situations too vaguely? This will help you understand how much attention to detail a candidate has just from the way they answer your questions.
6. Reliability and Professionalism: One of the common concerns for business owners outsourcing tasks is whether or not the virtual assistant can deliver results. Due to the nature of the virtual assistant industry, you will likely be working with virtual assistants from other countries, like the Philippines. The last thing you want is a virtual assistant who’ll bail on you a month after their starting date. So it’s always important to look for signs of reliability and professionalism in their responses. Do they discuss how they manage deadlines and prioritize tasks? Do they provide examples of their time management strategies?
7. Proactivity: At A Team Overseas, we’ve always highlighted the importance of productivity as a skill to look for and nurture when you hire a virtual assistant. Your VA should not just be a task-taker but someone who can, through a successful onboarding with your help, eventually drive their own growth and become a strategic partner for you. You might eventually run out of things you need a virtual assistant to help with, but a great VA can take the initiative and identify new opportunities to add value to your business — whether that be through process improvements, identifying potential issues, or constantly looking for ways to take more off your plate.

Hire Remote Executive Assistants with A Team Overseas

This comprehensive guide should get you on the right path toward hiring a VA who’s the right fit for your needs. Now, if you’re interested in receiving full support during this journey, at A Team Overseas we offer virtual assistant services so you can hire VAs that are more than task takers. We offer continuous support to ensure you not only find the perfect VA but also work together most efficiently. Contact us today if you’re interested in learning more about our services!