You scroll through profile after profile. Everyone is “detail-oriented,” “proactive,” and “5+ years experienced.” You finally pick a virtual assistant, spend hours onboarding them… then end up fixing their work at midnight and answering your own emails again. Sound familiar?
If you’re a small business owner, hiring a VA can feel like gambling with your time, money, and sanity. So how do you actually evaluate a virtual assistant’s experience before you hand them the keys to your inbox, calendar, and clients?
Why “Experience” Is More Than Years on a Profile
“3–5 years of experience” sounds impressive. But experience only matters if it lines up with your real-world needs.
You don’t just need “a VA.” You need someone who has done your kind of work for your kind of business using your kind of tools. That might mean managing social media for local service businesses, building simple reports in Google Sheets, or keeping a busy founder’s inbox under control.
A bad hiring decision can cost a business a lot in time, money, and lost momentum. When you bring in the wrong VA, you’re not just paying their rate. You’re also paying with your attention, rework, and missed opportunities.
Meanwhile, the freelance world is exploding. There are more virtual assistants than ever before. The challenge is not “Can I find a VA?” but “How do I know this VA has the right experience for me?”
The 4 Pillars of a VA’s Real-World Experience
Think of VA experience as four pillars. If one is missing, things wobble. If several are missing, things fall over.
1. Portfolio and Past Work
Ask to see real examples:
- Social posts they created and scheduled
- Email drafts or newsletters (with private details removed)
- Simple reports, trackers, or SOPs they’ve built
You’re not just checking grammar. You’re looking for clarity, consistency, and whether they can follow instructions.
2. Client Outcomes and Testimonials
Past clients should be able to say what changed because of this VA. Maybe they got more consistent posting, faster response times, or fewer missed deadlines. Even small outcomes matter.
If you want a simple decision framework, check out this guide on avoiding the wrong VA with a simple hiring system.
3. Systems and Process Experience
Great VAs don’t work from memory; they work from systems. Ask:
- Have they used tools like Trello, Asana, ClickUp, or Notion?
- Are they comfortable with content calendars, recurring tasks, and checklists?
- Have they followed or helped create standard operating procedures (SOPs)?
This is where you separate “I can help with anything” from “I know how to run repeatable processes.”
4. Communication and Initiative
Experience also shows up in how they communicate. Do they:
- Ask clarifying questions instead of guessing?
- Summarize decisions and next steps?
- Proactively flag issues before they become emergencies?
You’re not just hiring hands; you’re hiring a thinking partner who helps you stay organized and on track.
A Simple Step-by-Step Process to Vet a Virtual Assistant
Here’s a straightforward process you can copy and use for every VA hire.
Step 1: Define the Role Clearly
Write down 5–10 recurring tasks you want off your plate and what “success” looks like for each. For example:
- “Reply to basic inquiries within 24 hours.”
- “Schedule three social media posts per week that match our brand voice.”
The clearer you are, the easier it is to judge whether a VA’s experience fits.
Step 2: Shortlist for Relevance, Not Just Price
Instead of sorting by lowest hourly rate, look for:
- Similar industries (local services, coaches, ecom, etc.)
- Similar tasks (inbox, social content, admin, research)
- Familiarity with your tools (Gmail, Canva, WordPress, CRM, etc.)
If you’re still not sure where to even begin, this guide on where to find a virtual assistant when you don’t know where to start is a helpful companion.
Step 3: Ask Targeted Experience Questions
Trade vague questions like “Tell me about your experience” for specifics:
- “Tell me about a client similar to me. What did you handle for them?”
- “How do you manage conflicting deadlines from multiple clients?”
- “Which tools do you use to keep yourself organized?”
You want stories and examples, not slogans.
Step 4: Run a Small Paid Test
Give them a realistic, paid test that mirrors the real work:
- Draft three social posts from a brief
- Clean up a messy inbox
- Build a simple content calendar
During the test, watch not only what they deliver but how they communicate while doing it.
If you want more ideas around VA roles and tasks, you can explore related VA-driven social marketing articles for inspiration.
Red Flags When Evaluating a VA’s Experience
Some warning signs are subtle. Others are screaming. Pay attention if a VA:
- Can’t give specific examples of past work or outcomes
- Won’t share a portfolio or anonymized samples
- Claims they can “do everything” with no real specialization
- Is slow to respond or gives confused answers during the trial
One wrong hire can slow everything down. The right one makes your whole business feel lighter.
Stop Guessing. Get Help Matching With the Right VA.
Here’s the hard truth: most small business owners are already stretched thin before they start hiring. You’re juggling sales, delivery, marketing, and support. Adding “VA recruiter” on top of that is a lot.
You didn’t start your business to live in your inbox, chase invoices, and babysit underqualified hires. The right virtual assistant can give you back entire days every month — but only if you choose someone with real, proven experience.
That’s where having a hiring partner makes life easier. Instead of guessing from profiles and buzzwords, you get help defining the role, screening for real-world experience, and finding a VA who already knows how to support founders like you.
If you’re ready to stop rolling the dice on VA hires and start building a support system that actually frees you up, it might be time to talk to someone who does this every day.
👉 Click here to book a free consult with Global Digital Media. Use that call to walk through your needs, get clarity on the type of VA you really need, and take the next step toward a business where you’re not doing everything yourself.
Recommended Video: How to Hire a Virtual Assistant
If you like learning visually, this short video walks you through practical steps for finding and hiring a virtual assistant. It’s a great way to see the process in action before you start applying the tips in this article.
