If you’re still spending your day buried in scheduling, inbox triage, or chasing down that one document from two weeks ago – you're costing your business. Every hour you spend doing low-impact tasks is an hour you're not leading, building, or growing.  

That’s why hiring a virtual assistant isn’t just a convenience. It’s a strategic move to reclaim your time, refocus on your Unique Ability®, and finally operate at the level your business demands. 

But not all VAs are created equal – and the difference between a time-saver and a time-suck often comes down to the interview. 

As the Recruiting Director at WorkBetterNow, my department sees 4,000+ applications come in every month from highly skilled professionals in Latin America. And through our proprietary Top Talent Filter™, we accept only the top 2% of candidates as WBN Certified Professionals™. 

How do we do it? The process our applicants go through is a rigorous one that has been carefully designed and constantly improved to give our WorkBetterNow clients the best talent available.  

If you’re considering hiring a virtual assistant, there are some normal concerns you may be facing that you would like to address through your questions. Below, I’ve grouped sample virtual assistant interview questions by common concerns that small and midsize business owners have when hiring remote talent.  

Common Concern #1: Will they be reliable, responsive, and accountable? 

One of the biggest fears business owners have about hiring a remote assistant is not knowing if that person will follow through. These questions help reveal a candidate’s sense of ownership, time management, and integrity. 

1. Do you have a dedicated workspace? Describe it for me. How does it help you with your day-to-day tasks? 
2. Tell me about a time when you had to juggle multiple urgent priorities. How did you stay on track? 
3. How do you communicate if you’re going to miss a deadline or if you’re running behind? 
4. When working remotely, how do you stay focused and make sure you’re being productive throughout the day? 
5. What systems do you use to track your time and stay organized? 
   

Common Concern #2: Do they have the skills and experience to actually help me? 

Resumes only tell part of the story. These questions help you assess whether your candidate can hit the ground running – or will need hand-holding from day one. 

1. Can you walk me through your experience with [insert tools you use – e.g., CRM, email platforms, project management software]? 
2. How do you approach learning a new tool or process you haven’t used before? 
3. Have you supported clients or teams in [your industry or function] before? What kind of tasks did you handle? 
4. What type of projects or responsibilities are you most confident in managing? 

Common Concern #3: Will working across time zones be an issue? 

Many business owners worry that hiring someone in another country will lead to communication delays, missed meetings, or availability issues.  

By only providing talent from Latin America, WorkBetterNow clients in the United States and Canada get fully awake professionals who are available for meetings, messages and phone calls based on the client's time zone.  

However, should you be interviewing a virtual assistant from a different time zone such as the Philippines, Africa, or Asia, you’ll want to use the following questions to gauge flexibility and clarity on the candidate’s time zone: 

1. What hours do you typically work, and are you flexible to adjust based on a client’s needs? 
2. How do you handle communication when there’s a delay due to time zones? 
3. Have you worked with clients in [your time zone] before? How did you make it work smoothly? 

Common Concern #4: Will I have to micromanage them? 

The whole point of hiring a virtual assistant is to free up your time, not create more work for yourself. The following questions uncover how well the candidate can self-direct, prioritize, and take initiative. 

1. How do you prioritize tasks when everything feels urgent? 
2. If I give you a project and only a high-level outcome, how would you get started? 
3. How often do you proactively update clients on your progress? 
4. What do you do if you realize you misunderstood a task or weren’t clear on expectations? 

Common Concern #5: Can I trust them to represent my business well? 

A VA may be communicating directly with clients, vendors, or team members. The following questions help you understand how they build trust and represent your brand. 

1. How do you ensure you understand and reflect a client’s tone and style when communicating on their behalf? 
2. Have you ever been asked to handle sensitive or confidential information? How did you approach it? 
3. How do you handle mistakes or misunderstandings with clients or team members? 
4. Tell me about a time you had to communicate bad news to a client or supervisor. 

Bonus Tips for Maximum Interview Clarity  

Before you begin interviewing candidates, I want to share a couple of tips to help you complete an interview with the highest levels of clarity.  

First, ask for specific instances. For example, “Tell me about a time you...” When candidates tell you a story, they quickly reveal to you their thinking and problem-solving patterns.  

And second, my number one tip for when you feel like you haven’t gotten the clarity you’re looking for is this: “Tell me more.”  

As humans, we are quick to agree with a person with whom we are speaking, and we want to move on to the next question, task, or meeting. But pressing a candidate to go deeper on a question – rather than asking more questions – will often provide the details you need. 

Final Thoughts: Don’t Go It Alone 

Hiring a virtual assistant is a smart move for growing your business – but getting it right does not only take asking the right questions. You must also have the right talent pool, the right firm with checks and balances to limit your risk, and the right hiring procedures to make the process as quick and easy for you as possible.  

That’s why WorkBetterNow was built – to provide small and midsize businesses like yours with pre-vetted, full-time virtual talent from Latin America at one flat monthly rate. No surprises. No gimmicks. Just top-tier professionals ready to help you scale. 

When you’re ready to hire, our team sets up three qualified interviews in just one 60-minute window – a streamlined approach designed for busy entrepreneurs like you. 

Ready to find a remote professional that can help propel you and your business forward? Schedule a consultation with WorkBetterNow today to find out how easy hiring remote talent can be.  

WorkBetterNow (WBN) provides outstanding remote talent to small and midsize businesses. WBN’s highly skilled and pre-vetted Latin American professionals are hand-matched for each client’s unique needs. Hundreds of growing businesses turn to WBN to unleash their potential through our exceptional talent, ease of hiring, and ongoing support. Request a consult today!