How to Interview a Virtual Assistant Before Hiring

I run a digital operations agency with 14 people, with a mix of full-timers, contractors, and virtual assistants. So, I can say I have experience in hiring. Plus, over the last six years, I've hired more than 30 VAs across research, admin, social media, and executive support.

I am not going to say all my hires turned out to be great; some worked out beautifully, others cost me weeks of damage control. The turning point came after a particularly bad hire in 2021. I went through multiple guides on “how to interview a virtual assistant,” but none helped.

It might sound dramatic, but that hire, let’s call her S for the sake of anonymity, turned out NOT to be everything she claimed in her resume. She knew nothing, and it showed on every task she picked. I lost one major retainer client over it. That was a wake-up call for me.

To be honest, I didn’t want this to happen anymore, so I re-evaluated my hiring process so that I don’t end up hiring someone like S again. I changed the questions to ask a virtual assistant before hiring and saw major changes.

Not going to gatekeep this information, so here's the exact process I use now, and the specific questions to ask a virtual assistant that have made every hire since then significantly better. I have broken it down into sections to share with you the answer to “how to interview a virtual assistant?” so that you don’t go at it directionlessly.

Problem-solving and prioritization questions

Ask them:

• "Walk me through how you handle it when three urgent tasks land at the same time."
• "If a client gives you unclear instructions and you can't reach them, what do you do?"
• "Tell me about a time a project shifted mid-way. How did you adapt?"

Communication questions

Ask them:

• "How do you flag a delay before it becomes a problem?"
• "Do you prefer check-ins or do you work best with full autonomy?"
• "If you made a mistake on a deliverable, how would you handle telling me?"

Tools and workflow questions

Ask them:

• "Show me a process or workflow you set up for a previous client."
• "How do you make sure recurring tasks don't slip through?"
• "Which tools do you use to manage your own task list and why?"

Availability and expectations questions

Ask them:

• "What does your typical workday look like, and where would I fit in?"
• "If something urgent comes in at the end of your day, how do you handle it?"
• "What does a successful first 30 days look like to you?"

Ownership mindset questions

Ask them:

• "Tell me about something you improved for a client that they didn't ask for."
• "Have you ever caught a problem before it reached your employer? What did you do?"

Now, these questions will tell you a lot about the person you want to hire. Base their answer on what you are looking for, and half the work of hiring will be done. You might come across someone who leaves a mediocre first impression, but try to understand how much the person knows, the tools they used, how they have owned their mistakes, and I think you will know if they are a good fit for you.