How to Tell if it’s Time to Hire a Virtual Assistant?

The Secrets to Hiring, Managing, and Streamlining Workflow

Hiring a virtual assistant can be a daunting task. Especially if this is your first time hiring someone else to take care of your baby, I mean your business! You know what I’m talking about. It's hard to pass off this business that has been your life, where you have exerted yourself, and where you have found success in. You built it with your own two hands. So some thoughts about bringing another person in may include, “I couldn’t possibly trust someone to do what I do or to know all my passwords and personal information... Let alone take on the responsibility of providing a consistent paycheck to another human being!” I hear you. 

I felt the same way when I hired my first virtual assistant, but as I have hired more and more contractors, freelancers and VAs over the years - 22 to be exact - I have learned its not as intimidating as I thought because I’m in control.....of everything! This is my business and the beaut! to owning a business is the flexibility it provides us. EVEN how much we pay them. I have learned some handy tips and tricks to hiring and managing contractors, especially Virtual Assistants, that I hope will make hiring and managing less painful and a bit easier for you.

Reasons to Hire a Virtual Assistant

First up, the main benefits to hiring a VA:

  • Saves you time.
  • Will help expand your business.
  • Will give you a break from the parts you don’t enjoy.
  • Provides a trial period before hiring them as employees.

Saves you time. Hiring a VA can save you loooads of time. If you feel like you’re already drowning in your business, like you’re spread to thin, or don’t have the time to dedicate to other areas in your life that need your attention, then hiring can definitely help. It can give you the time you need to do other, probably more important, things. This is the main reason most hire out.

Will help expand your business. Hiring a VA or contractor also can help you expand your business. I know you. You’re a busy-body, a doer, you are motivated! You probably have several things you want to do in your business but don’t have the time to do. A VA HAS that time that you need, so they’re able to dedicate more time, effort, and thought into a different area that you may not be able to dive into at the moment. OR they can give YOU the time you need to do this same thing and expand your business.

Also, hiring someone with an expertise in an area you don’t have experience in may also help expand your business to a new area. There’s a load of VA’s out there with ANY talents that you need. Seriously. You need web design, development, social media management, copywriting, you name it. They do exist. You just need to find them. More on this later.

Gives you a break from the parts you don’t enjoy. Yes! This too can be the only reason you hire a VA. If you are growing tired of monotonous work and spend hours doing this each week. Give it to someone else! It’s like a breath of fresh air. I think many businesses fail because people grow bored of it. But what if you could keep your business growing, still make money, and be less involved? I bet some businesses would still be around if the owner had just hired out the areas they didn’t enjoy anymore!

Provides a trial period before hiring. PLUS hiring a VA can also be a great way to test the waters with having another on the team. There’s no commitment if you don’t make one. You can send them things on a project by project basis and you don’t even need to cancel because as far as both parties are concerned, this is a one off job. I have hired several people in the past, two currently who I tested the waters with first before offering them on-going work. Someday I am sure I will need to make the next step to offering one a full time position as an employee. What better way to interview potential employees than to have them work for months before hiring the? Golden.

How do I know if it's time to hire a VA? 

One of the most important things to look at is how consistent is your income or your ability to produce income? When I first hired out, I knew that each week I’d have at least X amount of dollars to work with. I became consistent at projecting what sales would be and could always depend on a minimum amount.

Consistent Revenue

If you can depend on a certain amount of revenue, then you can hire a VA. Honestly. I get more into paying a VA below, but YOU are the owner of your business so YOU can decide how much to pay them and how much they work. All you need to do is work this into the contract in the very beginning. You need x, y and z from them and they can only work 5 hours a week tops. You’ll find someone that a few hours a week is all they’re looking for! Maybe even 2 hours a week. Many VAs are working for several clients so picking up another small gig that could turn into more down the road still speaks to them and gives them potential for the future. Because out of all the people hiring them, YOU may or may not be the one that sends them ongoing work. Don’t let money get in the way of hiring a VA. 

You also know it's time if you are feeling any of the ways I mentioned above. Spread thin, like you don’t have enough time, bored of your work to the point you may just quit, feeling like you want to expand or go in a new direction and need expertise, you want more time to dedicate to other things, or you want more time to dedicate to growing in a new area. If you are feeling at least one of these, it's time to hire a VA - even if it's just for a couple of hours a week.

Overcoming the Fear of Hiring or Managing Others

This is a big one I know for many of you (and it was for me too): self doubt. I had this doubt in my mind and insecurity that the freelancer I was hiring could see straight through me and would be able to tell I hadn’t a clue what I was doing. I didn’t know how to teach them, I didn’t know how to manage them, and it intimidated me to provide a paycheck for someone who was depending on it. This might be the same for you.

To this I recommend start small. Starting small relieves a lot of these fears. Give them a task to export files for you or make listing images. See how you both do with small, insignificant tasks such as these, then take a step further.

I’m a big fan on doing some thought work as well. You are having this fear because you, in your own mind, created it. It’s just a thought in your mind that is holding you back. But I believe there is an answer to every single fear we are feeling and a way to overcome that fear. Maybe your fear is a result of the unknown. Well how do we get rid of the the unknown? We do it! What about the problems that could happen? You figure it out as you go just like with everything else involved with being a business owner! #toughlove

Come up with a simple list of tasks or one task for your VA and start there. There’s one fear eliminated.

The Fear of Managing a VA

The most important thing I have seen to successfully managing another human being is communication - a work in progress for me, but nonetheless important! When both of you are on the same page with expectations and timelines and how everything is going to pan out, this relieves some of that fear of managing another human being. They understand, you understand, and more importantly you know they understand. They also know where you stand with your wants and needs. I know this can be intimidating and unnatural for some of you to bluntly communicate the “look, here is how its going to be” attitude to someone you don’t even know. But truth be told, they actually prefer this! It’s exhausting to them to try and figure out what you want. I promise it actually makes it easier for all parties. When problems arise between me and my VAs, its usually because I haven’t communicated these clearly.

Also realize that it is YOUR business. You can do whatever the heck you want. YOU are in control of everything that goes on and can back off of it if something isn’t working. OWN it! You are the leader here.

It's also good to realize that others are in fact teachable. You may be thinking you cannot possibly teach someone to do what you do but I assure you, you can. Any job is replaceable. Heard that saying before? This includes your job especially in the beginning. You simply need to find the right person. They’re out there.

Hiring a VA

Hiring a VA is probably easier than you may think. The freelancing sites I’m about to mention make it incredibly easy to do and to manage. Below are a few places I have hired and some of the most popular. If this is your first time hiring a VA, I recommend using a site like one of the ones listed below:

Freelancer was the first place I hired from. You’ll find that many freelancers are from other countries, which is also intimidating but worth it because these people will save you money! You can hire someone for as little as $5/hr instead of $10/hr here in the US. Some of them will try to rip you off, so be smart and know how much time projects will take and what you’re willing to pay. Some countries I have found to be better to hire from than others, simply due to their culture values being less or more similar to ours. I have not had success hiring from India. I have had more success hiring people who live in the Philippines. This is not meant to be racist, this is just what I have noticed between those who I have hired. also protects your money so you don’t release the full amount until you are satisfied with the work.

I eventually migrated from Freelancer to UpWork. I loved that Upwork has a built in time tracker that monitors the VA’s activity level, while also taking intermittent screenshots so you can see what they are working on. If they don’t log in, they don’t get paid. I have also found that UpWork has slightly better quality of freelancers overall. You can also sort which country you hire from or qualifications you want applicants to meet. 

How this works: You post a job with all the qualifications, requirements, budget and things needed. Then you wait for applicants. That’s it! You can message back and forth with certain ones and sometimes even hop on a phone call with them, then once you have found one you like, you hire them! Or if you don’t like any, you can cancel the job posting without paying a single thing. You don’t pay anything until you actually hire someone then UpWork or Freelancer takes a portion of this pay. Another perk to using one of these sites is taxes. You pay the website and then they pay the freelancer. No need to worry about 1099 forms at the end of the year, since these sites serve as a website you are paying instead of an individual.

This was the last place I hired from that I was satisfied with and felt matched my needs the best out of the three above. So definitely worth looking into. 

The Virtual Savvy

I haven’t tried this one yet but if I end up needing a full time VA down the road and don’t know anyone who would be interested, this is probably where I’ll go. They actually teach VA’s how to be a VA! Their Facebook group has 43K and its a jackpot for people like us! These are people who have been trained and are qualified so if you can afford to pay a little extra as I’m sure they require, this is definitely an option!If this is your first time hiring a VA, I recommend any of the above starting with cheapest option to more expensive. I recommend these if you are having trouble finding a VA. Although, if possible, I’d try using Word of Mouth to find someone if possible.

Word of Mouth

The best way I have found in hiring an amazing VA is simply through word of mouth. I have found that by hiring someone through people I know, my Vs are more consistent, dependable, and most importantly can do work independently without much supervision! Word of Mouth is usually the more expensive route so be aware of this.

VA Costs

Let’s talk about costs. When I first hired, I paid my VA $6/hr. I did this for a year and a half. She did her job and was dedicated, but I found I had to look over her work constantly. In the end, I didn’t have the time to keep doing this so we parted ways.

I should also mention that the task I gave my first VA was something that I knew how to do well and felt confident in teaching someone else to do.  This, I believe, is important when hiring. You need to have a thorough understanding of what you are giving them instead of trusting they know what they’re doing. I ONLY give my VA’s who have been working for me for a while and who I trust things that I am unsure how to do myself. The first VA had the one, simple responsibility to export my design files (and actually I still have my design assistant do this). The other VA I have now, and pay more and trust, I give her simple tasks I don’t have time to do but I ALSO give her tasks such as looking into a new fulfillment partner for me. This came with time. She earned work such as this. I didn’t just automatically give it to her right off the bat when she was first hired. 

Anyways, back to the costs. I now pay $10/hr to my design assistant and $15/hr to my VA who I know, trust, and want to keep! I know some of you are curious how much I pay so I wanted to give you these. Both are girls in college or recent graduates and are amazing! I will fight you if you try to steal them away. ;)  I hope this gives you a ballpark of what to pay your VA.

I’ve Hired a VA. Now What?


As I already mentioned, it good to have your ducks in line when hiring a VA. I do suggest trying your best to have your processes down and recorded so that no matter who fulfills this role, they immediately have training. 

I would first give your VA the areas of your business that can be systemized and provide a beginning-to-end process to. This will make it easier for them to learn and to run with. Not to mention observing and managing their work will be easier. 

I would also give your VA the areas that are a combination of insignificant tasks that constantly need completed - the areas that are still important but that anyone could do. The repetitive processes that you go through each day and really get bored of. Also ask yourself, what areas of the business can I be less involved in? Or what are the most important things I do? Then give the less important away. The most important areas in my business are the designs I create and the content I create. I don’t think I’ll ever completely give these to someone else but outside of this, Amanda does a lot.

What she does: Completely manages the shop while I am on vacation or doing a launch. This includes things like customer service, sending files to customers who can’t access their email. She also looks over my blog posts, she’ll take content I have in a Google doc and post it to the blog, she manages the Freebie Friday giveaways we do, she creates the product posts on Instagram for me, she helps create the guides for my course and look through content for typos and grammar errors, posts new products to Pinterest and the list goes on and on.

What she doesn’t do: Write blog posts, write Instagram/FB posts (minus the mentioned above), create, record or edit the video tutorials or course materials.

I’m trying to think of anything else, but that’s pretty much it! I do the content creation side of things and she does the time-sucking tasks that give me a headache. Love you Amanda!

Channels of Communication

It's important to establish a channel to communicate with your VA. The better the communication the more you get done. You want to make it easy for your VA to get ahold of you when they have questions. I’ve used everything from text messaging to Voxer (voice text messaging) to Marco Polo (video messaging). We also use a project management system which is a huge lifesaver. Workflow communication, aka accomplishing the everyday tasks consistently, is especially important. I have found that training my VA’s on the processes and setting up the framework to do perform these processes works best. Let’s talk more about workflow.

Streamline Workflow

The quicker you can streamline your workflow, the better. Eventually you may have your VA doing several things at once. A big part of streamlining workflow is having a dependable project management system in place. For us this is Trello (but I’ve also heard Asana is a good one).

I have learned that the better and more organized you are - the woman in charge - at using this software, the better your VAs can use it. Train them! Show them how to use it. Be sure to provide all the details, deadlines, priorities and processes on your project management system.

Here’s a screenshot of Amanda’s board. I keep her pretty busy, to say the least, but take note on the layout. My mind works in a very linear fashion, so this is how I have built the steps for her and ask her to keep it updated so I know where she’s at on things. You all might be more interested in our Etsy listing process:

 I have broken the process from designing to listing products on Etsy for each SVG design we create. So I have a list of designs I need to get to. Maria, my design assistant, has a list edits I need her to make on existing designs. I also have a “Design Phase”, “Design Finalized” and a “Filetypes and Listing Image Created” list. So the designs we make are actually going through a process. This process is the exact same process I have developed and used for years before hiring them. It's also the same process I teach you who are in my SVG design course. The point is: it's a PROCESS. It is laid out step-by-step for my VAs so its easy for them to follow and easy for me to see where they are at. Its our HUB for everyday tasks and it's amazing. I could not function without it.

In summary, everyone knows the process, everyone knows their part in the process and everyone has a part in it, even me. So if one person doesn’t do their part, we get backed up. Teaching and leading this in your business is important to getting things done.

Making a Passive Business Even More Passive

 Once your VA has the processes down and everything is working in harmony for the most part, now you need to go do what you set off to do in the first place! Spend more time with your family, expand to a new area like I’m doing now, whatever it may be. BUT don’t just let your VA go loose without any guidance or checking in. You are a BOSS now. A good idea is creating a meeting where both of you can connect once a week and discuss projects and deadlines. This of course depends on your business and what you’re giving your VA. If you are only giving them tasks such as exporting your files and preparing listing images, you can see what is going on most of the time in Trello. So just play it by ear and see what works best with you and your new VA.

Having a VA (and now two VAs) has freed up my time monumentally. This is how I’ve been able to have the extra time to build a course to teach you all what I know and love. Without Amanda’s and Maria’s help, I definitely could not have done this without them because I wouldn’t have had the time.

So enjoy your newfound time! I wish you the best in hiring a VA and hope this article has helped in some way.

I value your feedback and love to hear from you! Please leave a comment with any questions or just let me know what you thought of the article and if you found it helpful. Have a great rest of your weekend everyone!





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Hire Virtual Assistant Philippines

This is wonderful! Thank you for expressing and sharing your knowledge with us. I’m looking forward to learning more.

Hire Virtual Assistant Philippines

Thank you for this blog. Keep sharing this kind of blog.

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