Four Questions to Ask Before Hiring A Virtual Assistant

Four Questions to Ask Before Hiring A Virtual Assistant

With the virtual world in which we live, many organizations have opted to outsource certain jobs, virtual assistants being a popular choice. This is a blog post on four questions to ask before hiring a virtual assistant.

For about a year I worked as a contracted virtual assistant through a staffing agency (Belay Solutions). I was in a transition period with work and it felt like a decent option for earning income while we planned for a cross-country move. 

I’ve been a contractor before in various capacities. I’ve worked so many side gigs in my life: as a freelance photographer for myself and other brands, a substitute teacher, dog watcher, caterer, event worker, and who knows what else I’m forgetting… But I’d never done contractor work before in this capacity, as a consistent admin assistant for a company.

What seemed like a great part-time option at first, quickly turned into an experience of burnout and total exploitation.

These places sell you on the idea of remote work, flexibility, control over your day, and being your “own boss.” But the actual expectation is that you’re on call for the org during business hours. I had to keep track of all my time using a clocking program (I used Clockify) and submit reports weekly. As a W9 contractor, I was provided with no benefits (PTO, insurance, anything)… I was anything but my own boss. 

It was rough.

I’ll write a separate post on the very real stress and challenges that came with this type of setup. But for now, I’m offering four questions that companies should ask before hiring a staffing agency for a virtual assistant. That is, if you want to be thoughtful about human rights and the conditions your contractor is working under.

Ask how much the contractor gets paid. 

Ask what portion of the total invoice you’ll be paying will be received by the contractor. In my case, I took home about half of what my client paid each month. A common misconception when going through a staffing agency is that the contractors keep more of that total invoice amount. Please keep in mind that the staffing agency is likely taking a large chunk of it. So while it seems like you pay a lot, it doesn’t all go to your contractor.

On top of that, we’re W9 employees, so we pay all of our own taxes ourselves, whereas W2 employees typically have half of the tax withholding, approx. 12.5 percent, covered by the employer. I used to set aside approx. 25 percent of my checks. After I withheld taxes, my hourly rate was about $15 an hour. 

It’s important to ask about the hourly wage your contractor is making. Then do that tax math, and manage your expectations accordingly. 

Why is it important that you ask as the person hiring a VA through a staffing agency?

It’s actually written in some of these contracts that contractors aren’t allowed to tell the clients how much money they’re making. Not to mention the inherent power dynamics involved in the whole business model. You should ask. Know what the people on your team, whether they’re contractors or full-time employees, make. That’s part of what makes a responsible and aware employer.

Ask if the contractor receives any benefits through the staffing agency. 

In most cases, W9 employees don’t receive any meaningful benefits. With Belay, we weren’t given PTO, any types of insurance or retirement benefits, etc. They occasionally offered discounts on edible arrangement-type places, most of which were too expensive anyway to buy and unappealing for most folks. I know I didn’t want to blow my whole monthly earnings on discounted Hello Fresh meals 🙄 

Here’s an example of how the lack of benefits played out for me. I was contracted to work approx. 16 hours a week/65 hours a month. So if the company I worked for was closed for holidays, I still had to figure out how to get to that 65 hours. If I wanted to take time off, I had to make up the hours on other days. 

While it seems like it’s gonna be “all chill, good, and flexible” in your head and you’re thinking oh hey, I only need to work about three hours a day, it rarely works out that nicely. I worked during holidays, weeks when everyone else at the org was out, and the times I was “on vacation”. When I traveled for my sister in laws wedding, I worked all of those days to keep up with hours. It was exhausting and a recipe for burnout and resentment. On the rare days I didn’t work because I felt sick, I paid for it later. 

My suggestion:

If the staffing agency doesn’t offer the contractor benefits, at the bare minimum, the org can offer PTO easily to the contractor themselves. Don’t have the contractor “make-up” hours when you choose to close your office. Let them also have those hours off. Subtract them from the contract. If they’re sick, don’t ask them to make up the hypothetical three-hour allotment they would have had for the day. Stuff like that goes a really long way. 

It’s also just important to know what circumstances your contractor is working under. So if you know they have no health benefits, etc. and are making very little money, let that guide you in your expectations and treatment of the human being behind doing this type of work. 

Ask if the contractors receive raises, when they receive them, and if there’s a cap.

With Belay, we received raises after one year of working there and with a cap of I think $21 or $22 an hour. It’s hard for me to remember the exact details. Already, it’s not a lot, and when you’re withholding your own taxes, it’s even less. 

Ask about the process and costs to hire them directly.

Another aspect that isn’t fully considered by all before entering an arrangement like this, is that the contractor becomes very much immersed in your company. You build relationships with each other. The VA understand your preferences and needs, and they become very much like actual employees. What may have started out as an easy, part-time solution for you both, has now become a valuable workplace relationship. 

I thoroughly enjoyed the actual company I was matched with and felt very much involved and part of the org. Though I wasn’t making near enough money, I wanted to stay on with them on my own, so that I could make a liveable wage. It’s not something that I imagined happening before signing on with Belay, but here I was.

Turns out, the buyout fee is very large, around $20k in some cases. This means many orgs are unlikely to buy out their contractors. The contracts also state that you can’t just quit and go work for them. You have to take a two-year time period off or something like that. It’s ridiculously difficult and written in such a way that it makes it near impossible for the contractor to grow financially or move up with the org they’re working with.

So after you’ve invested all this time working together, the way out of the contract feels like a long shot. You’re either stuck with Belay or you have to leave the org for a better situation. 

Basically,

This is very much what exploitation looks like. And it’s important that it’s talked about openly and called out. As the responsible organization, these are the questions to ask before hiring a virtual assistant. If you don’t ask, it’s going to be really hard for your virtual assistant to get the courage to tell you, if they’re even legally able to. 

Always have open, honest conversations with the people on your payroll. It’s part of your due diligence as an employer, especially if you have any kind of DEI statement on your sites or handbooks. 

I can honestly say this was one of the most stressful times in my work life, and I’ve had quite a few. A true nightmare situation and I mean that. I know this setup works for some (though I’m not sure how). All I can guess is they have a partner who makes more, they live in a super low-cost city and want guaranteed remote work… But truly, as much as I’ve tried to imagine the ways it can work, it doesn’t make sense to me how anyone can sustain even basic needs on this setup. 

Picture of Greg from Succession with the caption "this is nightmarish"

I truly hope places like Belay change their ways completely or that they go out of business. As a place that sells itself on “Christian values” it’s not doing Christianity any favors. 

I have much more to say about this type of setup that I’ll save for later posts. But if you’re an org looking to outsource admin work through hiring a virtual assistant, at a minimum, you need to ask about and consider the above questions. 

If something seems shady, speak up. Because they’ll listen to ya’ll more than they’ll listen to the measly contractors. And that’s a fact. 

Click here for future blog posts on the topic.


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