How to Interview a Virtual Assistant Before Hiring

The first time I interviewed a virtual assistant, I treated it like a quick formality, almost like checking a box before onboarding. Big mistake.

Within two weeks, I realized I had hired someone who looked great on paper but struggled with communication, misunderstood priorities, and needed constant handholding. I spent more time fixing work than delegating it. That experience taught me something important: the interview is more about understanding how a VA thinks, communicates, and solves problems when you’re not there to guide them.

Since then, I’ve refined my interview process to a simple, repeatable flow that consistently surfaces the right fit. Here’s exactly how I do it and the lessons I picked up along the way.

I Start With Real-Life Scenarios, Not Generic Questions

I used to ask predictable questions: “Tell me about yourself,” “What tools do you use?” And predictably, I got rehearsed answers.

One day, out of curiosity, I asked a candidate this:
“If I need a task done urgently at 5 PM your time but you’re off for the day, what would you do?”

Her answer told me everything about her boundaries, communication style, and professionalism. That moment shifted how I interview.

What I ask now

• “Walk me through how you prioritize tasks when everything feels urgent.”
• “Tell me about a time a client changed their mind mid-project, and how you handled it?”
• “If I vanish during a busy week, what would you do to keep projects moving?”
• “How do you communicate delays or roadblocks before they become problems?”

My takeaways

• Scenario-based questions reveal the real person behind the résumé.
• I get a preview of how the VA problem-solves independently.
• I learn whether they default to silence, overcommunication, or proactive updates.

I Always Test Communication Skills Early

I’ve learned that a VA’s communication style will either become your biggest asset or your biggest bottleneck.

During one interview, a candidate gave me short, one-line answers. Not rude, just concise to the point of ambiguity. I realized later that working with them would require constant clarification emails. I didn’t move forward.

Now, I observe communication from the very first touchpoint.

What I look for

• Do they restate tasks to confirm understanding?
• Do they ask clarifying questions instead of guessing?
• Do they organize thoughts clearly and logically?
• Do they communicate proactively or wait for me to chase updates?

Quick communication test I use

I give them a short task description and ask:
“Can you tell me how you would approach this?”

The way they structure their response tells me 90% of what I need to know.

I Check Tool Familiarity With a Mini Walkthrough

I used to ask, “Are you comfortable using Asana, Notion, Slack, Google Drive?” Every VA said yes.

But comfort level varies wildly.

Now I ask them to show me how they’ve used a tool before. Not a full demo, just a quick explanation.

My favorite prompts

• “Show me a workflow you set up for a previous client.”
• “How do you organize tasks so nothing slips through?”
• “What’s your process for documenting recurring tasks?”

When a VA can explain their setups clearly, it’s a green flag. When they can't, it usually means they haven't actually used the tools as much as they claim.

I Always Include a Paid Test Task

This is the step I regret skipping in my early days.

A short, paid task reveals:

• How they handle instructions
• Whether they meet deadlines
• Their attention to detail
• Their decision-making without supervision

I’ve had candidates who interviewed brilliantly but froze during the test task—or missed obvious instructions. I’ve also had quiet candidates who absolutely crushed it.

My go-to tasks

• Creating a simple research summary
• Drafting a short email on my behalf
• Organizing a messy Google Sheet
• Creating a 3-step SOP from a Loom video

What I evaluate

• Accuracy
• Clarity
• Structure
• Speed
• Follow-up questions

I Have a Real Conversation About Expectations

After a few poor fits, I realized misalignment doesn’t come from skill gaps, it comes from mismatched expectations.

So I now have an honest, open conversation during the interview.

What we talk about

• Working hours and overlap
• Turnaround times
• Preferred communication style
• How to handle urgent tasks
• How feedback is given (and received)
• What success looks like in the first 30 days
• Their preferred work environment and workload

Every time I skip this conversation, I regret it.

I Look for the “Ownership Mindset”

The best VAs I’ve worked with don’t wait for me to assign every micro-task. Instead, they anticipate needs, suggest improvements, and keep things moving without me hovering.

I always ask:
“Tell me about a time you took initiative without being asked.”

The candidates with an ownership mindset always light up. They speak with pride. They give examples. They show me they think like a partner, not a task-taker.

I Validate Their Claims With Thoughtful Reference Checks

I don’t treat reference checks like a formality anymore.

Instead of asking generic “Were they good?” questions, I dig deeper.

What I ask references now

• “How did they handle stress or deadlines?”
• “What was their communication style like day-to-day?”
• “Were there any blind spots you wish you’d known earlier?”
• “Would you hire them again? Why or why not?”

You’d be surprised how much insight you get from the phrasing, tone, and pauses.

The Bottom Line

Interviewing a VA is less about checking qualifications and more about understanding how someone works when they’re on their own. After years of trial and error, I’ve learned that the right questions, the right scenarios, and the right expectations make all the difference.

If I were starting from scratch today, I’d follow this exact checklist:

My Final Interview Checklist

• Ask scenario-based questions
• Evaluate communication from the first message
• Check tool familiarity with real examples
• Give a paid test task
• Align expectations openly
• Look for ownership mindset
• Verify with thoughtful references