How Do You Give Feedback to a Virtual Assistant When You’re the Nice One?

So why does your VA still seem so unsure?

Why do they check with you before every small decision? And why does one short message from you seem to rattle them for a whole day?

We asked one of our VAs what it's like to work for a founder who feels like a best friend. Her first line stopped us.

"I loved the praise, but I didn't always know what I did right."

Why doesn’t praise tell your VA what to do next?

Praise tells your VA you're happy. It doesn't tell them what you're happy about.

So they can't repeat it.

Here's the difference.

"Great job on the client email!" feels kind. But your VA is left guessing which part was great.

Praise the behavior, not the outcome. Then your VA knows exactly what to do again tomorrow.

What does your VA do when they can’t tell where they stand?

They start reading the mood.

The same VA told us, "A change in tone, like a shorter message, can feel bigger than it is." And, "Sometimes I paid more attention to the mood than to my tasks."

Now think about what that costs you.

As a result, a capable person spends their energy decoding your messages instead of doing the work. Small mistakes feel huge to them, so they slow down and double check everything with you.

And their growth stalls. In her words, "I don't know what to improve."

You think the relationship is great. You never see the drag.

Which type of team leader are you?

In fact, most founders who lead this way are good people with big hearts. In our Five Accidental Bosses quiz, this pattern has a name. The Buddy.

So far, it's the most common of the accidental types in our quiz results.

The Buddy is warm, generous and quick with praise. Which is why their VA knows they're happy, and has no idea what they're happy about.

Not sure if that's you?

Take the Five Accidental Bosses quiz and find out in a few minutes.

TAKE THE FIVE ACCIDENTAL BOSSES QUIZ

Should you stop being friendly with your VA?

No. Stay warm.

Being friendly was never the issue. Instead, the issue is warmth without direction.

And I always add this. "Nice avoids the hard conversation, but kind, you lean into it."

This lesson is personal for me. Years ago, a VA on our team told me about a team leader who called her amazing and the best, every single day. She still left that job confused about where she stood.

In the end, that story became the reason we built Win Talk, how we talk to each other here.

How do you lead a virtual assistant with clear feedback?

You lead a VA with clear feedback by naming what they did and why it mattered, saying small things while they're small, saying them out loud, and writing down what "done" looks like.

Here's how that looks in a normal week.

That's why a short daily Scrum makes all of this normal. Feedback stops feeling like a big event, because it happens a little every day.

What changes when your VA knows where they stand?

They stop watching your mood and start owning the work.

Soon they bring you ideas instead of questions. Better yet, they fix small things before you ever see them.

That's the part most founders miss. Your VA doesn't need more praise. They need to know what to do with it.

It wasn't the person. It was the setup.

You thought your job was to make them feel good. Your job was to make them certain.

Key Takeaways

• ✓Praise tells your VA you're happy. Clear feedback tells them what to do again.
• ✓When a VA can't tell where they stand, they read your mood instead of doing the work.
• ✓Being friendly is fine. Warmth without direction is what leaves your VA guessing.
• ✓Name the behavior, say it while it's small, and say it out loud.
• ✓A Super Toolkit shows what "done" looks like, so your VA isn't guessing.

FAQ about feedback to a virtual assistant