The decision to hire a virtual assistant is a big one.

Perhaps you’re a busy professional looking to free up some extra hours during your day, or maybe you’re a business owner who wants to unload some of your more menial tasks so you can focus on working on your business instead of in it.

Either way, selecting a virtual assistant can be challenging, and choosing the wrong one can cost you more time than you’ll save.

You’re already familiar with the benefits of hiring a virtual assistant, which include not having to worry about payroll processing, employment taxes, providing a workspace, and other headaches. But how to choose the right virtual assistant for your specific needs?

Basic Rules for Virtual Assistant Success

Before you dive in, let’s cover some basic rules for success.

1. Have a plan. Before selecting a virtual assistant company or a freelance virtual assistant, it is critical you answer these questions:

  • What specific tasks will you want your virtual assistant to take care of for you?
  • Are these tasks ongoing or part of a one-time project?
  • Do you need your VA to be available during your business hours or can they work during your night?
  • Do you need a native-English speaker?
  • Do you need a full-time or dedicated resource?
  • What is your budget?

2. Do your homework. Although there are many options when it comes to selecting a virtual assistant, not all services are equal. Find out what they specialize in and if they will be able to deliver the results you require.

3. Check the reviews. Seek out reviews on various virtual assistant services. There’s no need to venture out into uncharted waters when thousands of others have gone before you. Use their experience and feedback to shape your decision. Of course, past performance doesn’t guarantee future success, but selecting a virtual assistant company with positive reviews is certainly smarter than selecting one with consistently negative ratings.

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Probably the most common question I get is “which VA company should I choose?”

And I wish I had the million dollar answer! The truth is there is no “best” outsourcing company and all are good at different things.

What I would do is narrow down your options using the Virtual Assistant Assistant directory, and then see if you can set up an intro call.

The purpose of that call is to see if the company is a good fit for the role you have envisioned.

Here are a few questions I’d consider asking on that call.

13 Questions to Ask a VA Company

1. How are assistants assigned?

Are they going to take inventory of your prospective tasks and find someone who’s a good fit skill-wise? Or assign you to the first-available, who may have just been “fired” by their client?

2. What happens if it’s not a good fit?

Is there a probationary or trial period? If after a couple weeks it’s not working out, what happens? Will they assign a new VA? Refund the time and part ways?

3. Can I set my preferred working hours or time zone availability?

It’s not always necessary to have your VA working in your same time zone, but it can be nice to have that option, especially at the beginning for training and questions.


4. Can I interview my prospective assistant first?

Some would say not having to go through the screening and interview process is an advantage of working with a VA company over a freelancer, but I still think it’s a good idea to try and get on a Skype call with your prospective VA first.

Do they communicate well? Can you see them being a valuable part of your team?

5. What happens when my assistant quits / is sick / is on vacation?

Basically, what back-up plans are in place? Is the sick/vacation time paid or unpaid?

6. Do you have experience in my industry?

Of course most companies will say they can handle any and every task you throw their way, but I’d dig a little deeper to see if they’ve done the specific work you have in mind before.

And if not, it’s not the end of the world, especially if you have a system in place to train them. But that leads to point #7…

7. Do you have any references I can call?

Sure, the reviews on are a great starting point, but it can be helpful to talk one-on-one with current or previous clients.

8. Do you accept credit cards?

This is a nice selling point for me, mainly because I’m usually working on some travel hacking credit card sign-up bonus with a required amount of minimum spending. VA time can be an easy way to rack up a lot of miles.

9. How are hours / tasks assigned and tracked?

What’s my communication going to look like? Do I have a new interface to learn?

If you’re billing hourly, how do I know my VA is really working during those hours.

10. What security measures do you have in place?

Now as you know, it only takes one bad apple to cause a security breach whether in the office next door or in a remote working situation.

What I’m really listening for here is some response that shows they’ve thought it through and recognize this as a concern for clients.

11. Why do short-term clients end their relationship with you?

This is an optional question, but it’s kind of like asking a job candidate why they left their last job. Was it a case of misaligned expectations? Were they not happy with the performance? Did they find another service provider?

12. What’s the best way to make the most out of your service?

You might get some interesting responses to this one.

One company just said to “use us”, where another provider explained how the assistant they were thinking of assigning me to also had an extensive background in social media graphics, something that would definitely come in handy down the road. But they don’t always offer this information up!

13. What do your long-term clients have in common?

This shows you’re thinking long-term and want to know how to position yourself for a lasting relationship. It also might give you a hint to the type of businesses that find a good fit with this company.

Your Turn

What do you think?

What other questions would you ask?

If you’re on the VA side, what questions should prospective clients ask?