In the last post, I said that once you know you need support, the next question is who. This is the part where most people overthink the resume and underthink the conversation.
I understand the urge. A skills list is concrete. You can scan it in thirty seconds and tell yourself you’re being thorough. The problem is that skills are also the easiest thing to fake, learn quickly, or list without actually being good at. They tell you very little about whether someone will fit how you work.
The real test is the conversation. So I want to share what I look for when I’m on either side of a hiring chat.
Pay attention to the questions they ask you
A good VA isn’t just answering your questions. They’re asking some of their own. About your business. About how decisions get made. About what’s worked with previous support and what hasn’t. About how you like to communicate when something goes wrong.
If you finish the call and realise they didn’t ask much of anything, that’s information. Either they assumed the work was simple, or they were performing instead of listening. Neither bodes well for the months ahead.
Listen for how they describe past clients
This one tells you almost everything.
If someone speaks about their previous clients with respect and specificity, that’s a strong sign. They’ll say things like “she ran a small consultancy and I helped her with quarterly planning” instead of “I worked with a few businesses doing admin.”
If someone speaks about previous clients with vague exasperation, take note. The way they talk about the people they used to work for is how they’ll talk about you to the next person.
Watch how they handle a small disagreement
Bring up something you might do differently than they suggested. Not as a trap. Just as a natural part of the conversation.
What you want to see is someone who can hold their ground without getting defensive, or update their view without folding. Both of those skills matter once the work starts. A VA who can never push back will let you head off a cliff because they don’t want to upset you. One who never updates their view will dig in on the wrong thing.
Notice the small admin of the conversation itself
Did they show up on time. Did they follow up after with a clear note. Did they spell your name right. Did they remember something specific from your earlier exchange.
I know this sounds obvious. It’s also one of the most reliable signals I’ve ever found. How someone handles the small admin of the hiring conversation is usually how they will handle the small admin of working with you.
The fit question matters more than the fee question
I’m not suggesting fee doesn’t matter. It does. But if your decision is dominated by fee, you’ll end up in a relationship where you’re constantly second-guessing the value of small asks.
When the fit is right, you stop counting hours so closely because the work actually moves things forward. When the fit is wrong, no hourly rate is low enough to make it feel okay.
Worth a little extra time
Take more time with the conversation than you think you need. Ask the questions you would ask a future business partner, because that’s closer to what this person becomes than you might expect.
Coming up in my next post, I’ll talk about what to do once you have the right person. Hiring is only half of the equation. The first thirty days are where most VA relationships either settle in or quietly drift.