Hiring Your First VA: Common Concerns of Business Owners

Hiring a VA - Concerns Working with a Virtual Assistant by Emily Reagan PR

Lessons from a Digital Marketing Virtual Assistant who actually does the work:


You’re probably here because you’re a business owner who is thinking about hiring your first Virtual Assistant. And I know that’s a pretty daunting task. So today I want to talk about some of the common concerns about hiring a VA that I hear from business owners all the time.

Whether you’re brand new business owner or an experienced solopreneur who is just used to working completely on your own, you probably have had a course or a coach who has suggested that you hire a VA.

And you’re probably intrigued, but there are a lot of doubts, concerns, and obstacles on that path of hiring a VA.

So here are six of the most common roadblocks that I know clients have about expanding a business team and hiring that first VA. And my own thoughts and suggestions about what you can do next.

1) It costs too much money.

How can you afford to hire a VA when some days it feels like your business is barely moving forward? Let alone bringing in the revenue streams of your dreams?

So many business owners have this concern about hiring a VA for the first time.

I’m going to twist this back around, because that’s exactly the reason that you can’t afford to NOT hire a virtual assistant!

It’s cliche but I don’t care. Because I know it’s true. You have to spend money to make money.

Every business has upfront costs and capital needs. This is no different than investing in your new computer, an upgraded camera, your latest coaching course, or your monthly mentor group. 

Nobody wants to spend more money when you’re just starting to see profit. But if you don’t build the infrastructure you need, you’ll never be able to scale.

And the good news is that you set the budget. There are no required rules. I know many business owners who have started their new VA with just a few hours a month. And then it grows when you start to see the return on your investment.

Maybe you’re just not making money with your online biz at all yet. In that case, you may have to step up your 1:1 services or in-person services to pay for it. Many successful entrepreneurs were doing a bit of both for a while.

Just keep reminding yourself it is worth the investment to lay the groundwork for future growth.


2) I’m not ready – I just don’t know enough yet.

Trust me – nobody is every truly ready!

We all suffer from imposter syndrome. And you might struggle to see how you could be a successful leader of a team when it feels like you’re barely able to pull off the role of successful business owner in the first place.

But that’s ok. Because you’re going to learn as you go.

And that’s one of the benefits of hiring a capable and eager unicorn VA.

You can be open and honest with your unicorn hire about where you are. Ask your new virtual assistant to help you figure out the ropes of how to make this work. You’ll get through it together.

Nobody expects you to be perfect. You’re going to make mistakes. I know I’m not perfect – ha!

Learning how to lead and how to delegate is a skill that has to be practiced and refined. You’ll get better the more you do it.

There are plenty of books, podcasts, and online business gurus who can give you the tips and advice you need.

And the rest of it? It comes from hiring a VA that you can trust and communicate with openly. And embracing the fact that this is another big area of growth that you can (and will) conquer.


3) I’m not ready – my business is a hot mess.

Again – this is where I’m going to turn it back on you and say that this is exactly WHY you need to hire your first unicorn VA.

Because I’ll be honest – we’re almost all a mess behind the scenes.

I know of 7- and 8-figure earners who are complete disasters behind the curtain of the pretty graphics and fancy courses.

Trust me. If you’re recognizing yourself right here, you definitely need to hire a virtual assistant sooner rather than later.

And you’re going to want someone who is organized, with attention to detail, who can help fit the puzzle pieces together and get things moving forward.

Take a little bit of time first on your own to analyze your needs, consider what tasks are a priority, and decide where you will need to tap into your unicorn’s own strength and expertise.

Be ok with things being a little messy at first. And have your VA start right away with documenting your onboarding procedures, your SOPs, and your organizational wrinkles that need to be ironed out.

You’re still going to need to do the work. You can’t just drop a giant mess in the lap of your new virtual assistant and expect them to magically fix everything on their own.

But you definitely won’t have to do it alone.



4) I’m the only one who can do it.

So many business owners have this concern about hiring their first VA! Even if they won’t openly admit it. 

I get it. This is your baby. And it’s hard to drop it into the hands of someone new, even when you know they are capable and talented. Like leaving your child at daycare for the very first time.

But keep your focus on the big picture. By handing off some of the drudge work and the tedious tasks to a new virtual assistant, you have the time and energy to develop your business where it really counts.

That can only happen if you let go of perfectionism and the urge to micromanage. Because you’re going to lose your all-star unicorn right away if you smother them.

On the other hand, don’t be afraid to ease in slowly. Begin with a lot of coaching and feedback. Have a clear brand voice guide and SOPs for important procedures. 

If’ something is a big deal to you, make sure you’ve made that clear.

Again, communication is key. Don’t be afraid offer feedback and constructive advice.

You’re not handing over the keys to the castle. You’re still going to be there every step of the way.


5) Once I do this, I’m stuck.

Afraid that once you make the decision to hire a VA, you’re going to be locked in? And stuck paying a lot of money for something that just isn’t working?

Well, good news. It doesn’t have to be that way. At all.

Sure – many of the big 8-figure teams have permanent employees, with salaries and benefits and all of that.

But it’s taken them a long time to build up to that level.

When you’re first starting out, you can hire a virtual assistant as an independent contractor. Which makes it a lot easier to cut ties if things just don’t work out.

And you can start small with a trial run. Offer your new VA a 90, 60, or even a 30-day contract for a set number of hours.

At the end of the trial contract, you can reevaluate and think about how you want to move forward.

Some small business owners might even hire a few different VAs for a handful of one-off projects. Short, single sets of tasks with a clearly defined end goal.

In this situation, you can get a feel for whether an individual VA clicks with your style and brand, and how well you work together.

Once the trial project is completed, you’ll feel feel more confident about extending your partnership into a longer term contract. Or you’ll know that maybe it’s time to move on and look for other options.

Just remember that even though this feels like a huge decision right now, it doesn’t have to be high-stakes situation. And you can easily set yourself up for flexibility and options for the future.

6) But I just can’t find the perfect person.

This is another common mistake when hiring your first VA. Once you’ve decided to make that leap, you come up with a mile-long laundry list of everything you want that VA to do for you.

It’s ok to have a dream list. But the reality is that even if you hire a unicorn, you’re not going to find someone who can jump in and do every single thing right away.

And if you do find that person, you’re going to have to pay them $100+ an hour for that level of expertise.

I’ve been doing this for many years, with many successful clients, and there are still so many things that I don’t know myself.

When I say that you need to hire a unicorn because they know ALL THE THINGS, I don’t mean that they have experience in every single platform and tech tool.

Instead, they know the big picture. And they have the confidence to figure out the details and tech skills as you need them.

But even a unicorn will never be perfect. They will always have their strengths and weaknesses.

I know that I have a lot of tasks that I can pull off for my clients, but they aren’t going all going to be top-of-the-line productions. There are still plenty of platforms and tech skills that I don’t know a lot about. We’re all only human.

Instead, pick your top priorities. Maybe it’s building your email list, hiring a Facebook community manager, or setting up a monthly box subscription service. Maybe you need to add content and strengthen your SEO game.

Look for a unicorn that has the strengths to meet those challenges head on. Then let them dabble in your other wish list items. As your business explodes, you can hire more people to fill those other skill sets you need.


Want to take a deeper look at how a VA can help the back end of your business?

Take a listen to this podcast episode where business consultant Kristen Westcott explains how she has built an entire business over helping business owners like you get organized, and how a VA can be vital to that process!

Subscribe: Apple Podcasts | Spotify | Libsyn | iHeartRadio  | Listen Notes

The Takeaway: It’s normal to have concerns when you’re hiring your first VA, but you don’t have to let that stop you.


Sure, it’s true that some business owners just really aren’t ready to hire a VA. They aren’t serious about their business yet. Or they just aren’t ready to invest more time and money into its growth.

But it’s all about mindset. If you have the fire, the passion, and the dedication to see your business rocket forward, then you need to get past these roadblocks and take that next step.

You won’t be the first (or last) business owner to get stuck on these concerns when hiring your first VA. But you’ve got to come to terms with them and get yourself out of the weeds.

And if you’re ready to hire but aren’t sure where to begin, I can help! Go over to hireaunicorn.com to fill out my free referral form.

I’ll pass along your job post to my private network of unicorn VA students!

Or if you need just a little more motivation, take a look at the FB live video I did on this exact topic: 

Investing in human capital is part of scaling up.

You’ll stay stuck on the weeds if you don’t!

Get out of the weeds and back in front of your business!

– Emily, Digital Media Virtual Assistant AND Small Business Owner


I help smart women learn the in-demand digital marketing strategies and tech skills to get hired as a unicorn virtual assistant.

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Before you go, make sure you grab my freebie for up-and-coming digital media freelancers and VAs:

Get my list right here of the top 10 tasks that business owners always ask for help with!


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    Meet Emily

    Emily Reagan is a jill-of-all trades when it comes to digital marketing and techie skills. She’s worked as a behind-the-scenes digital media implementor and virtual assistant for a decade for online biz owner clients.

    She’s a mom of four, Air Force wife, and founder of the Digital Media VA Crash Course, where she teaches smart women the in-demand, highly-coveted digital marketing skills to get flexible, online work.


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