7 Mistakes You’re Making with Your Virtual Assistant (Why They Keep Quitting Or Failing To Meet Your Expectations)

Do your VAs keep quitting? Or do you keep hiring a virtual assistant, only to realize they’re not the magic fix you were hoping for? Maybe every VA you bring on disappears after a few months, leaving you back at square one. Today, we’re going to talk about 7 Mistakes You’re Making with Your Virtual Assistant.

Whatever your experience with virtual assistants—or any service provider, really—if this sounds familiar, you’re not alone. The truth is, hiring and keeping great VAs isn’t just about finding the right person. A lot of it comes down to how you set them up for success—and how you set yourself up for success, too.

So today, I want to dive into the real reasons I think virtual assistants quit and, more importantly, how you can create a work environment that makes them want to stay.

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I am really excited about this topic because it was kind of inspired by two things. First, I saw a post on Threads where someone said, “Every single VA I hire—or maybe they just said anyone I hire to help me in my business—ends up starting their own business and leaving me high and dry.” Basically, it felt like their hires were just learning all their tricks and then taking off.

The second thing that inspired this episode was a Facebook group post where someone said, “I’ve gone through four VAs in six months. I don’t know why. I don’t know if I’m hiring wrong or training wrong, but something clearly isn’t working in my process—and I’m the common denominator.” Shoutout to that person for recognizing that, because it’s not always obvious what you could be doing differently. Especially in the online space, where we’re constantly hearing how great things are, it’s easy to think, why isn’t it great for me?

And as I was outlining this episode, I realized I actually have a lot of experience in this area. I’ve now been in business for over eight years, and I probably made my first hire—well, I say “hire,” but I mean contractor—back in 2018 or 2019. I can’t remember exactly when, but it’s wild to think I’ve been doing this for that long. Over the years, I’ve made mistakes, I’ve learned a ton, and I’ve done a lot of growing in the leadership department, which I definitely want to talk about in another episode at some point.

But for today, I just want to focus on the biggest mistakes I see people making with virtual assistants. And if you’re really interested in this topic, make sure to scroll back to Episode 34, where I had Sophie Robinson—a virtual assistant—share more of her experience from the other side of things.

1. Over-glamorizing Entrepreneurship

The first mistake I see people make is over-glamorizing entrepreneurship. This ties back to that post I saw where someone said, “Everyone I hire ends up quitting to start their own business.”

And here’s the thing—if you’re constantly talking about how amazing it is to run your own business, it’s not surprising that people start thinking, Why am I doing this for someone else when I could just start my own? That feels like a very natural response.

I do think there’s been a shift toward more transparency in the online space—at least that’s what my echo chamber is telling me. But at the same time, as the boss, you often feel like you have to make everything seem great. You don’t necessarily want to burden your team with the challenges or struggles in your business. That said, I do believe that sharing some of the ups and downs makes things more realistic.

And just to put it out there—I know at least one person on my team is probably listening to this. I don’t think I’m perfect at this, and I don’t think they’re judging me for it. But I still feel the need to add this little disclaimer!

To be clear, I’m not saying you have to work yourself into the ground to keep a VA or any other team member. But let’s be real—if I were working four hours a day and making a million dollars, I imagine it might be harder to retain people. Not impossible—plenty of people with those lifestyles have long-term teams—but if you’re finding that this is a recurring issue while also presenting that kind of effortless success, it might be worth looking at whether that image matches reality.

Because if behind the scenes, you’re actually working late nights, dealing with the emotional rollercoaster of entrepreneurship, and feeling all the highs and lows—that’s normal. And I think it’s okay to share some of that.

I personally love being an entrepreneur, and I would never discourage someone from wanting to start their own business. But at the same time, I don’t think entrepreneurship is for everyone. There are ups and downs, and not everyone wants that level of uncertainty.

I was recently reading Zero to One by Peter Thiel, and one of the things he said was, If you’re not going for gold, entrepreneurship isn’t worth it. Now, I don’t necessarily agree with that in such an extreme way, but I do think there’s some truth to it. The highs of running a business can be incredible, but the lows can be rough—and it’s those highs that make the tough times tolerable.

But if you’re only sharing the good parts, of course people are going to want that.

2. You Don’t Have An Onboarding Process

The second mistake you’re making with your virtual assistant—the one that makes hiring and growing a team so much harder—is not having an onboarding process. Are you bringing someone on and immediately throwing tasks at them on day one? Because if that’s the case, a bad start almost always leads to high turnover.

If your virtual assistant is overwhelmed, confused, and not given clear expectations, they simply won’t last. One way this was phrased to me once was: It’s incredibly disempowering to feel like you’re not getting it or doing a bad job when you’ve been set up to fail. And that really stuck with me. As someone who works with women and for women, I want my brand to be empowering—and that has to start with my team.

A lot of times, when we make our first hire (which Sophie and I talked about in her episode), it’s because our business is on fire. We’re desperate for help, so the second we find someone, we’re like, Can you start tomorrow? Here’s 85 different things I need done. Then, when things aren’t done exactly how we envisioned or when our new hire doesn’t even know where to find things, it creates a rocky situation on both ends. That’s why a solid onboarding process is so important.

Since I have us here, I’ll walk you through my current onboarding process. It’s not perfect—I’m still refining it—but I recently hired someone at the beginning of January, so here’s what I did:

• I record quarterly Loom videos for my team where I go over business goals, updates, and key things they need to know. Since I had just recorded one, I gave it to them to watch. I think an introduction to your business and mission is key. I want my team members to feel as enthusiastic as I do about helping women grow their businesses on their own terms—through blogging, through Pinterest, through getting found organically so they don’t have to constantly hustle on Instagram. I hope they believe in these things just as much as I do.
• I provided access to our standard operating procedures (SOPs) document. It’s still a work in progress, but I spent a lot of the last quarter refining it. My business coach (who I think I mentioned before) forced me to do this—and honestly, I’m so glad she did. It needed to happen. But at the same time, recording Loom videos on a Saturday night—the only time I could fit it in—had me pulling my hair out.
• I gave them access to my Blogging for Bingeable Brands course (which is usually $97) for free. It’s about two and a half hours of content and walks them through the fundamentals of how I write a blog. That way, the core training on blog writing was already covered.
• I did a full tour of where we house all of our materials (ClickUp) and where they’d be able to find tasks and additional resources.

All of these pieces are so important in an onboarding process. Without them, you’re throwing your new team member into the deep end without a life vest. And that’s not a great way to set them—or yourself—up for success.

3. Being Vague in the Definition of Done

The third mistake I see people making is being vague in the definition of “done.”

I was listening to Buy Back Your Time by Dan Martell, and one of the points he made really stood out to me. Sometimes, hiring a virtual assistant doesn’t save you as much time as it could because you are being vague about what “done” actually means. You have to be super clear.

Let me explain what that means. Let’s say you assign the task “write a blog post.” Someone might write the post in Google Docs, or maybe they’ll put it into WordPress and say, Okay, I wrote it. Done! But I caught myself making this mistake a lot in the beginning—because then I’d go in and add the formatting, the images, the alt text, the meta title, the meta description… I was still doing SO MUCH of the final work that my VA could have done if I had just told them that was part of the expectation.

So instead of saying, “write a blog post,” the task should be something like:

• The blog post is considered ready to review when:
  • It’s within the correct word count (guidelines provided).
  • It includes internal and external links.
  • The SEO tool shows a score of 80%+ or a green rating.
  • Images are resized, reformatted, and alt text is added.
  • The meta title and description are optimized.

That way, by the time I look at it, everything is already done, rather than me having to fill in the gaps.

And I would say that especially with your first or second hire, you’ll probably still be doing the last 20–30% of the work, thinking, Oh, whatever, it only takes me a few minutes. But trust me—as your business grows, that 20% becomes more and more and more, until it’s completely unmanageable. Ask me how I know.

So anytime you assign a task, ask yourself: What does “done well” actually look like? Be clear about that from the start, and don’t be afraid to refine it as you go).

4. Keeping Your Virtual Assistant Detached From The Results

Again, in Buy Back Your Time, Dan Martell talks about the 10-80-10 rule as a good approach to outsourcing.

• The first 10% is you setting the strategy and direction.
• The middle 80% is your VA or team member executing the task.
• The final 10% is you reviewing and finalizing the work.

And I do think this is a great framework to start with. But if your virtual assistant is just checking tasks off a list with no idea why they matter, they’ll feel disconnected.

Especially now, in 2025, people want to see the impact of their work.

Think about it—if they’re managing Pinterest for you, but they never see the analytics improving, they won’t feel the same level of investment. If they’re helping you with content, but they never hear feedback from clients saying, Wow, this is the best blog post I’ve ever read!, they won’t feel that their work is meaningful. If they create a Reel for you, but never know whether it led to engagement or inquiries, they’ll feel detached.

That doesn’t necessarily mean the quality of their work will drop. But they’ll be less invested in your business. They’ll be more likely to take a different opportunity or disengage over time.

Your working relationship will be so much better if they see the real impact of what they’re doing. And beyond that, it connects back to what I talked about earlier your company’s overall vision.

I don’t want my team to feel like they’re just sitting in a room writing content for me. I want them to know that the work they do helps our clients.

For example:

• That blog post they wrote? It’s helping a client get found on Google.
• That Pinterest strategy? It’s driving traffic that could lead to sales.
• That content plan? It’s giving a business owner freedom—more time with their family, more flexibility, less pressure to be constantly online.

That’s a huge part of why I love what I do. Helping female business owners grow on their own terms is one of my favorite things in the world. So why would I leave that out when working with my team?

So that’s one of the mistakes you’re making with your virtual assistant—keeping your virtual assistant disconnected from the bigger picture. If they feel like their work is making a difference, they’ll be so much more engaged, and way less likely to leave.

5. Treating Them Like a Vendor Instead of Part of The Team

A lot of times, as business owners—especially when we’re hiring under pressure—we’re just thinking, I have way too much to do, I need someone to check off these tasks. And trust me, nobody understands that feeling more than I do.

However, there are small things that can make a big difference in making sure your VA doesn’t feel like a task robot, if that makes sense.

One of the biggest things? Saying thank you.

And not just saying it, but saying it genuinely and often. I wake up every day feeling so grateful for my team. I can’t believe I have such an amazing group of people who seem just as invested in my mission as I am. It truly feels like they love the work as much as I do, and I don’t take that for granted.

I tell them all the time—literally, even when I’m paying an invoice, I’ll say, Thank you so much!

I’m so grateful to be paying this invoice because I’m so grateful for the work they do.

Another big thing? Checking in on their workload.

Sometimes we overload our virtual assistants (or team members in general) and then wonder, Why aren’t they getting things done? Well, it’s because they’re overwhelmed. They’re staring at a massive to-do list, unsure what to prioritize, and maybe even feeling paralyzed by the amount of work in front of them.

Checking in on workload regularly is so important when someone is part of your team.

For example, I had a team member who worked with me on and off for a while because my business was still growing. But they were so fabulous that I wanted to work with them more. I was constantly asking, What’s your availability two months from now? I think I first reached out in October and was already planning for January! I wanted more of their time, and I made sure to communicate that.

This is a big part of treating someone like a true team member—while also respecting the fact that they own their own business. If you’re hiring contractors, you’re not their only client, and you have to be super respectful of that.

The last point under this is giving them space to take ownership of projects instead of just following orders.

This is something I’m constantly working on. But I love when people bring me ideas on how to improve things or say, Hey, I tried this—what do you think? That’s the kind of initiative I want on my team.

But here’s the thing—this has to be encouraged. People don’t always take that initiative naturally because they don’t know how it will be received. So as the business owner, it’s up to you to create an environment where they feel safe suggesting new ideas.

At the end of the day, if you want your VA to be truly invested in your business, you have to treat them like they’re part of the business. That small mindset shift can make a huge difference in how long they stay and how engaged they are in their work.

6. Not Paying Enough

Number six—and this one might feel a little harsh—but are you paying them what they’re worth?

If you’re paying below market rates, your VA will leave the second they find something better. It’s just reality. Competitive pay will always give you better retention.

Now, I also want to be clear—I’m not hiring in other countries just to pay less money. I have zero issue with hiring internationally, but I don’t believe in the mindset of, Oh, you can get a virtual assistant in the Philippines for $4 an hour. That’s just not the kind of business I run, and it’s not the kind of advice you’ll hear on this podcast.

At the same time, I also recognize that not everyone can afford to pay $65 an hour for a high-level VA with 20 years of experience. So if you can’t offer top rates, there are other ways to make the role more valuable to them—starting with not making all the mistakes I’ve listed in this episode.

But beyond that, things like flexibility in their schedule can make a huge difference. And obviously, depending on where you live, employment laws might mean you can’t dictate their schedule anyway. But in general, being mindful of their time and respecting their autonomy is important.

Another thing? Opportunities for growth. And I don’t mean “luring” them in—because that sounds like a trap—but genuinely giving them the chance to learn new skills, take on leadership, or work toward something bigger.

Performance-based bonuses can also be a great way to compensate someone beyond their base pay. And of course, tying them into the bigger mission of your business is another huge factor. Especially in the online space, where people are so aware of the potential out there, they want to feel like they’re part of something meaningful.

7. Giving Your Virtual Assistant Too Many Random Tasks

And finally, mistake number seven—which I’ve kind of touched on before—but are you giving them way too many random tasks?

I get it. I really do. I’ve said this a million times in this episode, but I understand that we often hire in a panic. We shouldn’t, but we do. And when that happens, we just want someone to come in and take as much as possible off our plate.

Maybe you’re thinking, I don’t have enough work for a full-time graphic designer. I don’t have enough work for a social media manager, an ops manager, or a bookkeeper. I need someone who can do a little bit of everything. And I totally get that.

But when you see job postings like:

“Looking for a VA who can manage social media, write blog posts, handle customer service, clean up my inbox, do bookkeeping, design graphics, update my website…”

…that is an entire team’s worth of work.

Yes, there are amazing generalists out there, and you can find someone who does a mix of things, but constantly switching between completely different types of tasks makes them less efficient, not more.

Instead, focus on a few core responsibilities and expand their role over time. Otherwise, you’re setting them up for burnout—or you’re going to need someone with a ton of experience, and their pricing is probably going to reflect that level of skill.

Quick recap of the seven biggest mistakes you’re making with your virtual assistant:

1. Over-glamorizing entrepreneurship and not letting them see the full picture.
2. Not having an onboarding process to set them up for success.
3. Being vague in the definition of “done” and expecting them to read your mind.
4. Keeping them detached from the results of their work.
5. Treating them like a vendor instead of a team member.
6. Not paying them what they’re worth (or not finding other ways to compensate).
7. Throwing too many random tasks at them instead of focusing their role.

So if your VAs keep quitting, it might not be them. If this is happening to you all the time, you’re the common denominator. And it’s not just about people quitting—it’s about people not being as efficient as you expected, or not taking as much off your plate as you were hoping.

I really believe that addressing these seven things can make a huge difference. And I say that as someone who has made literally all of these mistakes at some point.

So take a step back—think about which one of these you’re going to work on today.

And if this episode was helpful, I’d love to hear from you! Send me a DM on Instagram @thekarareport or leave a review—it would mean so much.

Talk to you next week!

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