380. When Your Team is Actually Holding You Back

How to Leverage Existing Relationships for Business Growth
The most effective way to promote a new product launch, milestone, or sale is through warm outreach to people who have already said “yes” to your brand. Instead of cold-pitching strangers, businesses can drive massive visibility by re-engaging past press contacts, brand collaborators, vendors, retail partners, active affiliates, and loyal customers. Because these groups already know your value, a simple, mutually beneficial message asking them to share your news often results in free, highly targeted promotion.

You hired help because you were drowning. But now? You’re spending more time managing that person than the work is actually worth. And you’re starting to wonder if bringing them on was the wrong hire for your business.

A wrong hire in a small business doesn’t just cost you money. It costs you brain space, strategic momentum, and the freedom you were trying to buy in the first place.

I just watched a friend go through this exact situation with her VA, and it was the push I needed to talk about something nobody really addresses: what happens when the person you brought onto your team is actually making your life harder.

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Why Do Business Owners Keep the Wrong Hire Too Long?

Most business owners hold onto a bad hire 2-3x longer than they should because of guilt, sunk cost, and the fear of starting over.

You’ve already invested the time training them. You’ve built systems around them. And the thought of going back to doing everything yourself feels like a step backward. So you keep giving them another chance, another meeting, another set of clearly spelled-out expectations.

My friend did exactly this. For months she complained about her VA. The VA was unreliable, moved due dates around for long-term projects without discussing it, posted the wrong content on the wrong days, and constantly needed reminders for recurring tasks that should’ve been automatic.

No matter how many times my friend met with her, followed up, set expectations… the VA somehow never really saw the problem.

My friend knew she needed to let her go. But she didn’t feel prepared to bring on someone new. She didn’t have SOPs documented. She wasn’t sure she could find someone who was both good at the creative stuff and the tech stuff. So she just kept putting up with it.

Sound familiar?

What Are the Signs You Hired the Wrong Person?

The clearest sign you hired the wrong person is when you’re spending more time managing them than the work would take you to do yourself.

That’s not a team member. That’s a second job.

With my friend, I kept reminding her of a few things:

The platforms weren’t niche. Her website platform and email marketing tool are super popular. About 99% of VAs know how to use them. This wasn’t some obscure tech stack that only one person on earth could figure out.

The tasks weren’t specialized. Nothing she was having this VA do was so unique that someone else couldn’t pick it up quickly. And while having SOPs is always ideal, whoever she brought in next might actually have a better way of doing things anyway.

She was net negative on productivity. Between making sure the VA had everything she needed, following up, meeting, figuring out why things weren’t done, editing things that were done incorrectly… she could’ve just done it herself in less time.

And yes, “I can just do it myself” is a slippery slope. You don’t want to fall into that trap for everything. But when you’re literally losing time by having someone else do it? That math doesn’t work.

What Is the Hidden Cost of a Bad Hire?

The biggest hidden cost of keeping the wrong team member isn’t their paycheck. It’s the mental load they create.

Even with all the tactical frustrations, the most damaging part of my friend’s situation was the mental weight. This person was taking up so much brain space, so much energy. The time my friend spent talking to me about her VA? We could’ve been strategizing her next business move instead.

It was genuinely holding her back.

And I know this firsthand. A couple years ago, I had a full-time VA in my business. I thought it would be amazing to have someone with no other clients where I was their priority.

What actually happened? I spent way too much time thinking about what to assign them next. Not because those tasks were going to make a huge difference in my business. But because I wanted to make sure I was getting my money’s worth.

That’s not strategic thinking. That’s busywork disguised as leadership. It was not the right fit for what I needed.

Here’s what that mental load actually looked like in practice: instead of spending my mornings mapping out a new email sequence or planning a promotion, I’d be scrolling through a project management board trying to find something to assign. Instead of recording podcast episodes or connecting with my audience, I was writing out detailed instructions for tasks that may not have even needed to happen. The “help” was pulling my focus away from the work that actually moves the needle in my business.

Is It Better to Have No Help Than Bad Help?

Yes. Having the wrong help is worse than having no help at all, because a bad hire drains resources you’d otherwise spend moving your business forward.

I want to be really clear: I am not saying you shouldn’t hire. You absolutely need to hire, and yes, sometimes before you feel financially ready. Because you can’t do the things you need to do to be financially ready if you’re trying to do it all yourself.

But keeping the wrong person because “at least I have someone” is like staying with that shitty partner you had in your 20s. You’d already invested so much time, and it felt better than being alone.

Nah. You need to kick that fool to the curb so you can meet the better person.

What Happened After She Finally Let the VA Go?

When my friend messaged me to say she finally did it, I could literally feel the weight had been lifted off her shoulders through the screen.

She apologized for bringing it up so much, saying it must have been annoying to hear about it all the time. I told her it actually wasn’t, because every time she brought it up, it gave me an opening to remind her to get rid of the VA.

And now? She doesn’t have to spend hours every week following up. She can take the time to really think through what the right support looks like for the business she’s building, so she can find the right people.

Sure, it means she has to spend a little extra time actually doing the work herself right now. But in her case, it’s actually less time overall than what she was spending managing someone who wasn’t pulling their weight.

How Do You Know If You Should Fire Your VA or Fix the Situation?

If you’ve clearly communicated expectations multiple times and the performance hasn’t changed, it’s time to let them go. The fix-or-fire decision comes down to one question: after real effort on your part, are they trending in the right direction?

This is not permission to fire someone after one bad week. People have off days. Miscommunication happens.

But if you’ve done your part to support them, set clear expectations, given them the resources they need, and it’s still not working? That’s your answer.

And sometimes it’s not even about them being bad at their job. Sometimes you just hired for the wrong position and they’re not the right fit for what you need.

Maybe you hired a beginner when you really needed someone more experienced. Maybe you hired a strategist when you just needed someone to handle the day-to-day. Maybe you hired a VA when you really needed a fulfillment person.

How Do You Know If You Should Let Someone Go or Fix the Situation?

Hiring the right team for your ecommerce business starts with identifying your actual bottlenecks, not just offloading whatever you’re tired of doing.

Having people on your team only works if you have the right butts in the right seats.

If you don’t have that right now, consider this your wake up call.

Q3 is right around the corner, which means Q4 is coming fast. Now is the time to buckle down and find the right support.

Don’t just hire to hire. Be ruthless about identifying your real bottlenecks so you can be intentional about who you bring on. Ask yourself:

  • What tasks are actually costing me the most time?
  • Which of those tasks require my specific expertise, and which don’t?
  • Am I hiring for the role I need, or the role I think I should fill?
  • What does “success” look like for this position in 30 days? 90 days?

One of the biggest hiring mistakes I see ecommerce business owners make is hiring a generalist VA when what they really need is a specialist. Packing and shipping orders is a completely different skill set than writing email campaigns or managing your social media calendar. Lumping all of that onto one person because you want to keep things simple often means nothing gets done particularly well.

Think about what’s actually clogging up your day. If it’s fulfillment, hire for fulfillment. If it’s content, hire for content. If it’s customer service, hire for customer service. Stop trying to find one magical unicorn who can do all of it.

The right person won’t need to be micromanaged. They’ll make your life easier from the jump. And if they’re not doing that? You already know what to do.

Jessica Totillo Coster your eCommerce & Email Marketing Strategist

Hi, I'm Jessica

eCommerce & email marketing strategist with 25+ years in retail, including running a 7-figure store as the only employee. I teach product-based business owners how to do less and make more.

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Hey Babe

I'm Jessica

After 20+ years in retail, owning my own brick + mortar boutique, and spending 3 years as the ONLY employee of a 7-figure eCommerce store…

I actually understand what it’s like to be an eCommerce entrepreneur doing all the things and wearing all the hats. 

I created eCommerce Badassery so I could teach badass product-based business owners everything I learned along the way.

Jessica Totillo Coster | eCommerce & Email Marketing Strategist for Product-Based Business Owners
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