12 Questions You Should Ask When Interviewing Your VA

15 Nov 2023 By: Michael Kansky

Updated: 14 Nov 2023

In today’s global workforce, a virtual assistant (VA) can be an invaluable asset for businesses of all sizes. Whether you need administrative support, social media management, or customer service assistance, hiring a VA can free up your time and help you focus on growing your business. However, finding the right VA for your needs can be a daunting task. To ensure you make the right decision, it’s important to ask the right questions during the interview process.

Uncover the essential questions to ask when interviewing your virtual assistant in this comprehensive guide.

Here are 12 essential questions you should ask when interviewing your VA:

VA interview questions you need to be asking

When it comes to hiring a virtual assistant (VA), asking the right questions is essential. Not only does it help you assess their qualifications and skills, but it also gives you a glimpse into their work style and compatibility with your business needs. To ensure you find the perfect VA for your organization, here are some additional questions you should consider asking:

1. What previous experience do you have as a virtual assistant?

While you may have already asked this question, it’s worth delving deeper into their previous experience. Ask about specific tasks they have handled in the past, such as managing calendars, handling customer inquiries, or conducting research. Understanding their level of expertise and the scope of their previous roles will give you a better idea of their capabilities.

2. Can you provide references from past clients or employers?

References are a valuable resource when evaluating potential VAs. In addition to asking for references, consider asking the candidate about their most significant achievements or success stories from previous roles. This will allow you to gauge their work ethic, problem-solving abilities, and overall performance.

3. How do you prioritize and manage multiple tasks?

As a VA, the ability to multitask and manage competing priorities is crucial. Ask the candidate to provide examples of how they have handled multiple tasks simultaneously in the past. Inquire about their strategies for setting priorities, meeting deadlines, and ensuring that nothing falls through the cracks. Their answers will give you insight into their organizational skills and ability to handle complex situations.

4. What software applications and tools are you familiar with?

In today’s digital age, VAs often rely on various software applications and tools to streamline their work. Depending on your business requirements, it’s important to ensure that the candidate is familiar with the specific tools you use or are planning to implement. Ask about their proficiency in popular productivity tools, project management software, or communication platforms. This will help you determine if they can adapt quickly and efficiently to your existing systems.

5. Are you comfortable working with different time zones?

Global businesses often require VAs to work across different time zones or be available for flexible hours. It’s crucial to determine if the candidate can adapt to these requirements. Ask about their previous experience working with clients or colleagues in different time zones and how they managed their schedules accordingly. Their ability to be flexible and adaptable will be vital in ensuring smooth communication and efficient workflow.

6. How do you handle confidentiality and data security?

As a VA, handling sensitive information and maintaining data security is of utmost importance. Inquire about the candidate’s understanding of confidentiality protocols and their experience in safeguarding sensitive data. Ask about any previous instances where they had to handle confidential information and how they ensured its protection. Their answers will give you peace of mind knowing that your business’s sensitive information will be in safe hands.

7. Can you provide examples of your problem-solving skills?

Virtual assistants often encounter unexpected challenges or roadblocks while working on tasks. Assessing the candidate’s problem-solving skills is crucial to ensure they can handle such situations effectively. Ask them to share examples of how they have resolved issues or overcome obstacles in their previous roles. Their ability to think critically and find creative solutions will be invaluable in supporting your business’s needs.

8. Do you already have another job? If so, where are you working and how many hours are you working?

This question is important to ask in an interview for several reasons. Firstly, it provides insight into the applicant’s current commitments and time availability. If they are working elsewhere, it may affect their ability to commit fully to the job for which they are applying. Secondly, it may assist in avoiding any potential conflict of interest situations. Lastly, it can also give clues about the candidate’s potential for multitasking, time management, and dependability based on the number of hours they are currently working.

9. How much money do you want to make?

Asking the question, “How much money do you want to make?” during an interview is important for several reasons. Firstly, it helps understand the candidate’s expectation in terms of compensation, giving insight into whether it aligns with the budget for the position. Secondly, it helps gauge how the candidate values their skills and experience. Thirdly, it could potentially save time for both parties by avoiding pursuing an offer that may not meet the candidate’s financial needs or expectation. Lastly, it could be a preemptive discussion to avoid any future dissatisfaction related to compensation. However, it’s worth noting this question should be presented appropriately and respects the laws in the specific location/country.

10. Do you have your own computer and Internet access? If you have access, how fast is your connection?

Asking this question is important during a Virtual Assistant (VA) interview because the nature of the job requires consistent, reliable, and fast internet connection. Since VA’s work is primarily online and the VA may be required to download large files, participate in video conferences, or access shared online workspaces, they need a strong and stable internet connection. Additionally, owning a personal computer ensures the VA can undertake tasks independently without having to rely on public or shared devices, thereby ensuring data privacy and security.

11. Will you work from home or from an Internet café?

This question is essential to understand the work environment of a virtual assistant (VA). It helps gauge the stability, reliability and security of the VA’s work setup. Working from home often suggests a more stable and secure internet connection, less distraction and increased data privacy, compared to working from a public place like an Internet café. Specifically, it helps ensure the VA can meet the demands of the job and maintain client confidentiality. It also gives a sense about the potential risks of interruptions or unsecured networks.

12. Please write a paragraph of why I should hire you. Don’t send a list of your experience; describe it to me. 

This question is important because it allows the candidate to demonstrate their communication skills, understanding of the job requirements and how their unique expertise or abilities can add value to the firm. It encourages the candidate to sell themselves beyond their resumes, giving a glimpse of their personality, problem-solving ability, creativity, and initiative. It also offers insight into their enthusiasm for the role, helping the interviewer assess cultural fit and their potential impact on the team. Asking the candidate to write their response also helps evaluate their written communication skills, a crucial aspect for a VA role.

Remember, the interview process is your opportunity to thoroughly evaluate potential VAs and find the best fit for your organization. By asking these additional questions, you’ll gain a deeper understanding of their qualifications, work style, and ability to meet your specific needs. Take your time, ask follow-up questions, and trust your instincts to make an informed decision.

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What are some key tips for a successful interview?

When it comes to conducting interviews, it’s important to ask the right questions in order to gain valuable insights into a candidate’s skills, experience, and suitability for the role. While there are many questions you can ask, here are a few key tips to keep in mind:

1. Can you provide examples of challenges you’ve faced in your previous role and how you overcame them?

Asking this question allows the candidate to showcase their problem-solving skills and demonstrate their ability to handle difficult situations. It gives you a glimpse into their thought process and how they approach challenges. Look for candidates who can provide specific examples and explain the steps they took to overcome those challenges.

2. How do you ensure effective communication?

Clear and timely communication is essential when working with a virtual assistant. Inquire about their preferred communication channels and their ability to provide regular updates on progress. Look for candidates who are proactive in their communication and can adapt to different communication styles and preferences.

3. How do you handle confidential information and ensure data security?

When outsourcing tasks to a VA, you need to trust that your sensitive business information will be handled with care. Verify their commitment to data security and confidentiality. Ask about the measures they take to protect data, such as encryption, secure file sharing platforms, and adherence to privacy regulations. Look for candidates who prioritize data security and have a strong track record in handling confidential information.

4. What is your approach to self-improvement and professional development?

A good VA should continuously strive to enhance their skills and stay up-to-date with industry trends. Inquire about the candidate’s approach to self-improvement and professional development. Look for candidates who are proactive in seeking out learning opportunities, such as attending webinars, workshops, or pursuing certifications. A growth mindset and a commitment to personal and professional growth are valuable qualities in a virtual assistant.

5. How do you handle feedback and criticism?

Constructive feedback is essential for growth, both for the virtual assistant and for your working relationship. Determine if the candidate is receptive to feedback and willing to make necessary adjustments based on your input. Look for candidates who can demonstrate their ability to handle feedback in a professional and constructive manner. A willingness to learn from feedback and make improvements is a valuable trait in a virtual assistant.

Remember, conducting a successful interview involves not only asking the right questions but also actively listening to the candidate’s responses and assessing their suitability for the role based on their answers. Take the time to delve deeper into their experiences, skills, and mindset to make an informed decision.

Key tools and reasons for pre-screening candidates

Pre-screening candidates is a crucial step in the hiring process. By carefully reviewing resumes, conducting initial phone or video interviews, and asking specific questions, you can narrow down your options and spend more time with the most promising candidates. This approach allows you to make the most informed decision when selecting your virtual assistant.

When it comes to pre-screening, there are several tools and techniques that can help you in the process. One important tool is the use of questionnaires or skill assessments. These tools can provide additional insights into a candidate’s suitability for the role. By creating targeted questionnaires or assessments, you can assess specific skills, technical knowledge, and personality traits that are essential for a successful virtual assistant.

Another tool that can be useful in pre-screening candidates is the use of software, apps, or systems to stay organized and manage workload effectively. Efficient task management is a vital skill for virtual assistants, and inquiring about the tools they use can give you an idea of their organizational abilities. Whether it’s project management software, task tracking apps, or a well-developed system, understanding how candidates stay organized and prioritize their responsibilities can help you gauge their efficiency and effectiveness.

Work-life balance is another important aspect to consider when pre-screening virtual assistant candidates. Working remotely can blur the boundaries between work and personal life, so it’s crucial to understand how candidates maintain a healthy balance. Asking about their strategies for maintaining work-life balance can give you insights into their dedication and well-being. Whether it’s setting clear boundaries, establishing a routine, or practicing self-care, understanding their approach can help you assess their ability to manage their personal and professional lives effectively.

Overall, pre-screening candidates is an essential step in the hiring process for virtual assistants. By utilizing tools like questionnaires or skill assessments and asking specific questions about organizational skills and work-life balance, you can gather valuable information to make an informed decision. Take the time to thoroughly evaluate candidates, and you’ll increase your chances of finding the perfect virtual assistant for your needs.


Hiring a virtual assistant is an investment that can greatly benefit your business. By asking the right questions during the interview process, you can ensure that you find a VA who aligns with your needs and work style. The twelve questions discussed in this article cover a range of crucial aspects such as experience, communication, problem-solving, and organization. Use them as a starting point to create a comprehensive interview plan and make an informed decision when selecting your virtual assistant. Remember, thorough preparation and effective interviewing techniques will lead you to the perfect VA for your business.

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Michael Kansky

Michael Kansky is a seasoned entrepreneur and the CEO of LiveHelpNow and HelpSquad, two innovative companies that specialize in customer service solutions. With over 20 years of experience in the industry, Kansky has cemented his reputation as a forward-thinking leader, dedicated to providing exceptional customer support strategies and technologies. Under Kansky's guidance, LiveHelpNow has become a leading provider of customer service software, offering a comprehensive suite of tools for businesses to enhance their customer interactions. From live chat and ticketing systems to knowledge bases and email management solutions, LiveHelpNow caters to a wide range of industries and boasts an impressive clientele. In addition to LiveHelpNow, Kansky also founded HelpSquad, a customer service outsourcing company. He recognized the increasing demand for top-notch customer support and aimed to bridge the gap by offering highly trained professionals who can efficiently handle customer inquiries on behalf of businesses. HelpSquad's team of experts ensures that businesses can provide timely and personalized support to their customers, resulting in improved satisfaction and loyalty. Kansky's expertise lies in understanding the evolving needs of customers and transforming those insights into practical solutions. By combining technology, training, and a customer-centric approach, he has revolutionized the way businesses approach customer service.