10 Questions to Ask Before you Hire a Potential Virtual Assistant

10 Questions to Ask Before you Hire a Potential Virtual Assistant
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You’ve decided to hire a virtual assistant to support you in your business.  

You’ve identified the tasks you need help with and have a few candidates in mind.  But you don’t know what to ask them to get hold of the information you need to hire the right virtual assistant.

Here are 10 questions to ask before you hire a potential virtual assistant:

1) Tell me a bit about your business and why you’ve chosen to work freelance?

The first question to ask before you hire a potential virtual assistant is a relaxed way to find out their WHY and weed out those who’ve under-estimated the level of commitment needed to stick with self-employment.  Any virtual assistant who’s worth their salt will answer this question with passion and enthusiasm.  

Becoming a VA takes hard work and determination on top of all the organisational skills they need to keep numerous spinning plates from crashing to the floor.


Unfortunately there are some chancers out there who see virtual business support as an easy ticket to flexible work freedom.  

Questions to ask before you hire a Virtual assistant

In an essay in Forbes, Molly Cain explains that certain people are more suited to self-employment than others.  Wanting greater flexibility and control isn’t always enough to cut it as a solo business owner.  Your virtual assistant also needs to be passionate about their work and understand how that fits in with your business:

“The self-employed thrive on an unbridled enthusiasm for their work. Otherwise you will quickly burn out and get discouraged.”

2) What’s your favourite way to communicate?

Every business owner and virtual assistant has their preferred method and style of communication.  Personally, I’ve always been awkward talking on the phone.  I like to see the person I’m speaking to so I’d rather speak using Zoom or Skype.  


But I know some people hate being on camera, so the idea of web conferencing would be horrifying to them.

In addition, if you’re someone who loves data, and minute detail, you’ll want to work with a Virtual Assistant who can provide you with the granularity you need, rather than a 20,000 ft overview.  For some people too much detail can be over-whelming or just plain boring! 


It’s really important that you and your virtual assistant are on the same wavelength when it comes to communication, because a lot can get lost in translation over long distance.  Use this question to understand how your potential virtual assistant’s communication style might fit with yours.

3) What are your key skills and strengths?

In his book, Virtual Freedom, Chris Ducker talks about the myth of the SuperVA.  He explains that there’s a common misconception that you’ll be able to find a single Virtual assistant with all the skills you need in your business:

"Think about it for a second – this is not the case in the ‘real world’, so why should it be the case in the virtual world?!"

It’s unlikely that you’ll find one individual who’s able to handle every part of your business because, let’s face it, a creative VA is probably not going to be amazing at number-crunching and spreadsheets. 


If you’re hiring a virtual assistant to fill a very specific role, you’ll need to know what your potential VA’s skills are so you can make sure they’re a good fit.

4) What are you not good at?

Questions to ask before you hire a Virtual assistant

This question is useful to gauge whether your prospective virtual assistant is comfortable telling you what services they don’t offer.  


It’s important to make sure you hire the right fit for your role, especially if it involves a number of skill sets.  

Knowing a potential VA isn’t good at a critical skill will allow you to make an informed decision about whether to give them time to learn the skill, search for someone else or hire an additional VA to create a small team.

5) Are there any jobs that you’re good at but prefer not to do

Michael Hyatt calls jobs that you’re good at but don’t love, The Disinterest Zone.  You’ll probably know from your own work that when you’re working in the disinterest zone you’re less productive and the quality of your work is lower than when you’re doing what you love.


Understanding what’s in your potential Virtual assistant’s disinterest zone is a useful piece of information because ideally you want them to spend as much time as possible doing things they’re good at and enjoy doing.


To make sure your team is producing the highest quality of work in the least amount of time you should aim to allocate tasks to the person who is the most passionate about it.

6) If you agreed to handle a task and realised you weren’t as comfortable with it as you first thought, what would you do?

We all like to make people happy and say yes to requests for help. Your potential virtual assistant is no different, especially in the early day when they want to make a good impression and be as helpful as possible.


But they should be OK with coming to you to let you know that they’re struggling so that you can decide together what the best approach is to getting the task done well.

7) How do you tend to handle positive and negative feedback?

Some people (myself included) are genuinely embarrassed by compliments.  If that’s the case for your potential virtual assistant, it’s good to know that in advance before you shower them with praise that makes them feel awkward!

Questions to ask before you hire a Virtual assistant

On the flip side, it’s good to know how they like to receive constructive, negative feedback as this will help you to build a smoother relationship.   

8) Do you have any back-up procedures to manage internet outages or hardware failure, so that you remain contactable?

In the unlikely event that your potential virtual assistant’s PC explodes, in the middle of a powercut and simultaneous cyber-attack on their internet service provider – it’s good to know that they have a plan in place.

You want to know you can reach your VA even if there's a technical issue

Do they have alternative hardware they can use?  Is there anywhere else they can go with a secure wifi connection (that won’t put your confidential documents or data at risk)?  You want to know that you’ll be able to reach your VA even if there’s a technical issue so it’s worth making sure that they have some options.

9) Do you prefer your client relationships to be more hands-on or hands-off?

I first want to be clear that I’m not advocating micro-managing.  But both business owners and virtual assistants are all different when it comes to the frequency of communication that they like and expect.


I recently spoke to one VA who said she would often go several weeks without any contact with one client.  She’d be set a task and left to get on with it until the deadline.


For her, that was ideal because she liked the opportunity to focus on her tasks with minimal distraction.  But for others, that could feel very isolating and they might prefer a more involved relationship with you.


Again, this comes down to personal preference but it’s important to find the right fit so you’re both happy with the relationship.

10) If I gave you a large number of tasks and you realise that you’re unable to meet a deadline, what would you do?

Questions to ask before you hire a Virtual assistant

The final question to ask before you hire a potential virtual assistant is designed to show whether they’re comfortable being honest with you. 


As in question 6 – your virtual assistant will want to be as helpful to you as possible, and may try to take on more than is humanly possible.  

If you’re not used to setting deadlines, it can be easy to under-estimate how long a task or project might take so it’s important that they’re comfortable telling you that your expectations are too high.  And that you’re OK with hearing that too.

If you’re reading this article it’s likely that this is the first time you’ve hired a VA for your business so you want to make sure that you ask the right questions.  The above list is by no means exhaustive.  


You’ll have other questions which are more specific to the tasks and role you’re looking to fill.  But if you ask these questions before you hire your potential virtual assistant you’ll have a solid foundation for identifying the right fit for you and your business.


Which of these questions do you think is the most important?  Let me know in the comments.

Enjoy the blog? Make sure you download your FREE guide to help you decide what to out-source to a Virtual Assistant.

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