Questions to Ask Before You Hire Your First Virtual Assistant

If you’re finding it difficult to juggle a lot of things at once, then you might look into the option of hiring a Virtual Assistant. 

You’re exhausted. You’re burned out. You do everything yourself that you often forget that there are a lot more important things needed to be taken care of. 

A Virtual Assistant allows you to free up and leverage on your time and focus on the more important aspects of your business. 

But, we understand the hesitation to hire and trust your first remote employee hence we recommend for you to properly do your research and first ask yourself these questions. 

Questions to Ask Before You Hire Your First Virtual Assistant

1. Why do you think you need a Virtual Assistant?

Do you really need another hand? Or do you just need a more efficient workflow?

Sometimes, just because you’re busy doesn’t mean you already need a Virtual Assistant. 

Have you looked into what makes you busy?

Is it the amount of tasks you have or your failure to practice prioritization?

Will hiring a Virtual Assistant improve your business or lifestyle? 

To give you a better idea, review all the tasks you’ve done, the time you did it, and the physical, mental, and emotional exhaustion you gained from doing that task. 

Also think about whether the lines between personal life and work gets blurred for you. 

If all of this adds up to the stress that you’re feeling, then you might need another set of hands and by that, I mean a Virtual Assistant. 

2. What is your personality type?

Are you the type of person who can work great with a more laid back person? Or do you need someone who could keep you in check? 

Not all Virtual Assistants are the same. 

You’re working closely with another person so it is important that your personality types do not clash, or at least, make sure your personality types would not make it difficult for both of you to communicate with each other. 

Try to find a Virtual Assistant that will complement your personality type to ensure a better workflow. 

3. How do you plan to communicate?

Are you comfortable with talking about your work everyday? Or would you like to communicate as minimally as possible? 

What communication channels are both of you willing to use? Do you prefer exchanging emails or phone calls? 

Do you want to stick to a strict work hour where that’s the only time to communicate or is it okay for you to be contacted any time of the day?

How would you like to establish your boundaries when it comes to communicating?

Also be sensitive with time zones. 

You’d both work more efficiently when roles and communication are perfectly laid out. 

4. Are you willing to compromise for a change, especially if you’re a perfectionist?

Now, this is the hardest part when you are a perfectionist. 

Most likely, as much as possible, you’d like to take care of everything yourself to make sure it is  perfect for you. 

But, that doesn’t always work when you want your business to grow. 

You’d now have to be aware and sensitive of how other people work on your business if you recognize your need for another person to help you run it. 

Realize that there is nothing wrong with trusting other people and there is always another chance for you to make things better if it doesn’t work out in the first try. 

That’s something you need to accept if you’re looking for growth for both you and your business. 

5. What do you want to outsource from a Virtual Assistant?

What kind of Virtual Assistant do you need? 

A General Virtual Assistant or a Specialized Virtual Assistant?

Are you outsourcing tasks or outcomes? 

If you’re outsourcing tasks, then a General VA might be more suited for you. 

If you just want someone to take care of repetitive but tedious tasks that are necessary for running your business but not necessarily growing it, find a General VA. 

You’d first need to show them your process. 

If you want someone who has better expertise on a specific process in your business to achieve specific outcomes, then a Specialized VA might be for you. 

Since a Specialized VA has a very specific skill set, it would be better to tell them what to do, instead of how to do it. They also tend to be more expensive than a General VA. 

Make sure you recognize what you’re trying to outsource from a Virtual Assistant to save you more time.

6. How much are you willing to spend on outsourcing?

A Virtual Assistant is an investment for you and your business. How much are you willing to spend on that investment? 

Always work within your budget. A Specialized VA might be more expensive than a General Va. 

How much help can you afford? Can you afford a full-time VA or a part-timer? 

Also remember that a more expensive rate does not equate to better service and vice versa. 

See how much you can spare with your budget then try to work it out from there and see how it goes. 

7. How will you and your Virtual Assistant best work together?

More than just being employee-employer, you and your Virtual Assistant will be teammates. 

You work alongside each other. You form a team.

Most probably, your Virtual Assistant already has their own work system and you also have your own. 

See if you can try to merge or compliment both of your systems so that you can work better together. 

Set systems for communication, task managing and project management. 

You also need to form a relationship founded on mutual respect to make it work. You both set standards and expectations from each other. You’re both trying to make a living here. 

The success of your VA will also be a success for you. 

8. How will you manage your VA? (e.g. tracking their time & performance)

Explore the many cloud-based services available to keep track of their time and performance. 

You can also ask them what they use for their past clients to give you a better idea. 

We know it can be hard when you’re working with someone remotely. 

You wouldn’t want to stress over whether your assistant is keeping on task. 

Don’t be afraid to explore which works for both you and your VA.

You need to learn together from each other. 

9. How involved do you want your VA to be in your business?

What kind of boundaries do you want to establish, aside from clearly defining their tasks?

Do you want them to be heavily involved in a certain part of your business? Or do you expect them to know the ins and outs in everything? 

Don’t make your Virtual Assistant work on planning if they are only task-oriented because it wouldn’t be fair to them.

Likewise, don’t only delegate menial tasks if you’re hiring someone more capable for other tasks than just something small. It will be insulting to them and they’d be unhappy working with you. 

10. What is your plan of action if your first hire is not a good fit?

Don’t be discouraged if your first hire is not a good fit for you. 

There are a lot of qualified VAs out there that could be searching for you too.

Don’t just dump every task to them once they start. 

Monitor their performance and see how they react and work in every situation. 

Try to make them work in a probationary period and give feedback on their performance and see if your contract with them needs to be terminated before you invest too much money on something that just doesn’t work. 


Take your time in answering these questions before you start on your search for a Virtual Assistant. Let your answers create a path for a better system for your business. 

Also we’d like to congratulate you! 

If you’re in need of a Virtual Assistant, then that means you and your business are in need of growth and growth is never a bad thing! 

To give you more clarity, book a free call with me! I’ll help you determine if you’re in dire need of a Virtual Assistant and I can help you upscale other aspects of your business. Just don’t hesitate! 

What’s holding you back in hiring someone to help you in your business? Do you have experiences? Share your story in the comments below! 

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