So You Don’t Regret It Later…

Hiring a virtual assistant is kind of like dating for your business. You’re looking for someone who you can trust, who communicates well, and who doesn’t panic when your inbox hits 1,492 unread messages. It’s not just about finding help. It’s about finding the right help.

Whether you’re ready to outsource your admin chaos or just dreaming about the day, here are 6 things you should definitely talk through with a potential VA before hiring them.

1. Skills & Expertise

Yes, you want someone with experience, but don’t get stuck thinking they need to check every single box right away.

Sure, it’s great if they’ve worked in your industry and already know tools like Dubsado, Flodesk, or Trello. But if they don’t? That’s not necessarily a dealbreaker. What matters is whether they’re willing (and able) to learn, and whether you have the time and capacity to teach them.

Think: Are you looking for someone to take over completely? Or someone to grow with your business over time?

Ask things like:

• “Have you worked with creatives before—photographers, planners, designers, etc.?”
• “Which tools and platforms are you most confident using?”
• “If you haven’t used [insert platform], how do you usually learn new systems?”
• “What types of tasks do you love doing most?”

2. Communication Style

This one’s big. A VA could be incredibly skilled, but if they ghost your messages for three days or flood your inbox with updates every hour, it’s going to be a problem.

Talk about how you actually like to communicate. Fast-paced and real-time? Weekly recaps? Voice memos all day long? Get clear about what works for you, and see if they’re on the same page.

Ask things like:

• “What’s your preferred way to communicate—Slack, Voxer, email?”
• “How quickly do you usually respond to messages during your working hours?”
• “Do you prefer scheduled check-ins, or touch base as needed?”
• “How do you handle urgent requests or time-sensitive tasks?”

3. Schedule & Availability

Just because you work best at 6am (or 11pm) doesn’t mean your VA does. Be upfront about the hours you typically work and what kind of availability you’re hoping for.

Are you looking for someone who works the same hours as you? Or are you fine with asynchronous support, as long as deadlines are hit?

Ask things like:

• “What time zone are you in, and what hours do you typically work?”
• “Do you take regular time off or observe specific holidays?”
• “Are you available for real-time communication when needed?”
• “What’s your turnaround time for new tasks?”

4. Values & Goals

This is where you get to dig a little deeper, because you’re not just hiring hands, you’re hiring a mindset. You want someone whose values align with your business and brand vibe.

Talk about what’s important to you (like transparency, creativity, or excellence), and ask what’s important to them. And don’t be afraid to ask where they’re headed in their business—it helps you see if this could be a long-term fit.

Ask things like:

• “What kind of clients do you love working with most?”
• “What do you value most in a working relationship?”
• “Where do you see your VA business going over the next year or two?”
• “What does a ‘great’ client relationship look like for you?”

5. Collaboration & Feedback

You need a VA who can take feedback without disappearing or taking it personally. If something isn’t working, you want to be able to speak up and know they’ll adjust without drama.

Same goes for collaboration. Do they like to brainstorm with you? Or prefer a list of tasks and independence?

Ask things like:

• “How do you prefer to receive feedback?”
• “What’s your approach when something isn’t working?”
• “Can you share a time when a client asked for changes—how did you handle it?”
• “Do you prefer collaborating on ideas or working independently?”

6. Processes

Systems matter. Even if your current “system” is a messy Google Sheet and a million sticky notes, you need a VA who can help refine that, not get lost in it.

Talk about how you do things now, and ask if they have suggestions for improving efficiency. The best VAs are full of ideas and love a good system upgrade.

Ask things like:

• “What’s your onboarding process like for new clients?”
• “Do you follow client systems, or prefer to build your own workflows?”
• “Are you comfortable documenting processes or building SOPs?”
• “How do you manage tasks and track deadlines?”

Final Thought:

The right VA won’t just “check off” your to-do list. They’ll become a true partner in your business. So take the time to talk through these six areas. Ask the questions. Get clear on your needs. And don’t settle for anything less than a great fit.

Ready to find your perfect-fit VA? Get in touch or hop on our waitlist right here. We’ll help you find someone who gets your business and your inbox.

Or if you’re curious about exactly what a creative VA can do for you or what kinds of things you can outsource to a creative virtual assistant, check out our blog here that includes our free list: 85 Things To Outsource to a Creative VA.