3 Must-Ask Questions Before Hiring a Virtual Assistant

How to Find a VA Who’s Not Just “Helpful,” but Actually a Lifesaver

Thinking about hiring a virtual assistant (VA)? Before you dive in, make sure you’re asking the right questions—the ones that go beyond “Are you familiar with Canva?” and actually show you how they think, solve problems, and support your business behind the scenes.

Hiring a VA can feel like handing over your baby (aka business) to someone new. Whether you’re trying to clear your plate of customer emails, social media scheduling, or product listings, you need more than someone who just checks boxes. You need someone who gets it. Who gets you. Who can think like a founder—and act like a trusted partner.

And no, their Upwork profile and polished resume won’t tell you any of that.

So how do you spot the real gems?

Here are 3 powerful, gotta-ask interview questions that’ll tell you way more than “How many words per minute do you type?”

1. “Can you walk me through how you’d handle a task you’ve never done before?”

This is a peek behind the scenes of how they operate when the directions aren’t perfectly laid out—and let’s be honest, that’s a lot of our lives as entrepreneurs.

👉 Why it matters: You’re testing for resourcefulness, not just skill. Anyone can do what they’ve done before. But can they figure it out when you’re neck-deep in launch mode and need help yesterday?

What a great answer sounds like:“I’d start by Googling or checking YouTube tutorials, then check in with you if I hit a wall. I like to document as I go so we can reuse the process later.”

🚩Red flag alert: “I’d wait for you to explain it.” (No, thank you.)

✨Real life example:When I was launching a new fragrance collection, I asked a VA to research trending scent descriptions. Instead of just copying what she saw, she organized them by fragrance family and even pulled keywords for SEO. I never asked her to do that—she just thought it would help. And it did.

2. “Tell me about a time you made a mistake at work. How did you fix it?”

Spoiler: Everyone messes up. You want to know how they handle it—and whether they come to you with solutions, or just leave you untangling the mess.

👉 Why it matters: You’re hiring a human. Mistakes will happen. The real test? Do they take ownership, communicate clearly, and learn from it?

What a great answer sounds like:“I accidentally uploaded a wrong file to a client’s Shopify page. I caught it quickly, reverted it, and messaged them immediately with a fix and how I’d prevent it in the future.”

🚩Red flag alert: “I’ve never made a mistake.” (Run.)

✨Tip from experience:The best VAs I’ve worked with own their slip-ups, fix them fast, and turn them into better systems. Like one VA who started making checklists for all repeat tasks after one shipping mistake. Boom—problem solved and documented.

3. “How do you like to receive feedback?”

This one’s often overlooked, but trust me—it’s huge.

👉 Why it matters: You’ll be giving feedback. Often. Sometimes in Slack at midnight. You want to know how they’ll receive it—and how they’ll grow from it.

What a great answer sounds like:“I like honest feedback, and I appreciate when it’s direct. I’d rather know exactly what’s not working so I can improve right away.”

🚩Red flag alert: “I prefer not to get negative feedback.” (Yikes.)

✨Pro tip:Ask yourself how you like to give feedback. Loom videos? Slack notes? Casual voice messages? Find someone who aligns with your style—because mismatched communication = silent frustration.

Bonus Question: Want to work with someone who grows with you? Ask this:

“What kind of projects get you excited?”This gives you a glimpse into whether they’ll just do the job—or love it. When a VA is excited about the work, you’ll feel it. They’ll bring ideas, energy, and enthusiasm to your biz like it’s their own.

Takeaways:

• Don’t just ask about software. Ask about how they think, handle pressure, and grow.

• Look for problem solvers, not just task-doers.

• The right VA will make your life easier, your biz smoother, and your time more focused on what actually matters.
  

Hiring a VA isn’t just about outsourcing—it’s about upgrading your business brain. And when you find the right one? Game-changer.