The Ultimate Checklist: What to Ask a Virtual Assistant Before Hiring

If you are considering working with a Virtual Assistant, these questions will help you get started so you both know what to expect.

Victoria Jenner

8/5/20265 min read

So, maybe you’ve finally decided to take the leap and hire a Virtual Assistant. First of all, if that is the case, congratulations! Recognising that you can’t, and shouldn’t, do everything yourself is a massive business milestone. If you are still in the 'just thinking about it' phase, this article is still for you. It might help clarify your thinking or maybe you’ll just store it away for later. That’s fine too.

Either way, you may be thinking about how you actually choose the right VA for you. How you vet someone well enough to feel confident and comfortable? What do you need or want to ask to make sure you and your VA are the right fit for each other?

Chosen well, your VA will genuinely make your life a million times easier. When you work with a high-level VA, it’s not just about outsourcing admin tasks (though it’s fine if that’s what you want to do); it is about working in partnership. The right VA will spot pinch points in your systems that maybe you haven’t noticed yet. They’ll be proactive and make suggestions to improve and move forwards. They’ll get to know you and your needs and will take away your overwhelm. To help you find your perfect match and avoid surprises down the line, here are some questions you might want to ask before signing on the dotted line.

1. The Financials

How do payments and packages actually work? VAs generally operate on one of two models or a mix of both, and you need to choose the one that aligns with your current business needs:

  • Retainer Packages: You pay for a set number of hours per month in advance (e.g. 5, 10 or 20 hours). This guarantees the VA’s availability for your business, making it ideal for ongoing, consistent support like inbox management or weekly operations. It usually means the VA prioritises your work over their ad hoc clients. It also means you keep a firm eye on your budget and what you are spending.

  • Ad-Hoc Hours: You pay as you go for sporadic tasks. While flexible, the downside is that the VA’s time isn't guaranteed, and you might find yourself waiting in line behind their retainer clients. Ad hoc can be a great way of a VA taking on a one-off project and can also be a good way for you to test out working together.

I am always happy to do either, or a mix of both. Retainer hours aren’t carried over so, for me, I suggest to my clients go with the lower retainer hours just to start with and ad hoc hours can then be added each month. Once you know what you really need, retainer hours can be increased in future months until you find the balance that is right for you.

  • Specific Packages: It is worth sharing that some VAs (myself included) have specific packages of certain work that means you know exactly what you are getting. I run packages for Social Media work and for School Leader work at present (with more packages on the way). Some VAs have email and calendar packages or newsletter creation packages. A package is a brilliant way of getting the right work done for your business and managing your budget so you know exactly what you are spending. At the moment, my new Social Media Content Package is proving surprisingly popular, but you need to look out for packages that match your identified needs. A good VA won't try to get you to sign up to anything that doesn't truly match your business requirements.

Ask them: Do you require payment upfront? How do you track your hours? Will I receive a breakdown of how that time was spent?

2. Time Boundaries:

Check their time limitations and their likely turnaround time (and know that this might differ for ad hoc vs retainer clients). Just because a VA works virtually doesn't mean they are on call 24/7. Clear expectations prevent late-night panic and help you maintain a positive relationship with your VA.

  • Turnaround Times: If you send a task over on a Tuesday morning, when should you expect it back? A standard turnaround time for non-urgent tasks is usually 24 to 48 hours. This will obviously depend on the size and complexity of the task.

  • Time Tracking: Ask how they handle tasks that take less than an hour. For example, do they round up to the nearest 15 minutes?

Ask them: What are your core working hours? What is your standard turnaround time for project tasks?

3. The Trust Factor:

Know in advance how you handle password sharing and access to accounts. Handing over the reins to some aspects of your business can feel incredibly daunting. Your VA will already have a secure, system in place to put your mind at ease and will expect you to want to know more about this before proceeding. Believe me, we know how important your business is to you (we are business owners ourselves) so a good VA will be happy to spend time talking you through this.

Look for a VA who uses secure credential-sharing platforms. For example, I prefer using a platform like LastPass. This allows you to share access to your tools, software, and systems without your VA ever actually seeing your raw passwords. You retain full control and can revoke access instantly if needed.

Ask them: What security measures do you have in place to protect my business data and client information? How will we share passwords and key information?

4. Continuity:

What happens when your VA goes on their holidays or is unwell? Because they are independent business owners (and not your employees), they manage their own time off. The upside of this is that you are not worrying about holiday pay or sick pay (see my blog on the surprising cost of a Virtual Assistant Vs an employee). However, you still need to consider what you will do if your VA is not around. Some VAs have associates that they can pass work on to if you are happy with that. A professional and reliable VA will give you notice well in advance of holidays so that you, and they, can plan their time well.

Ask them: How much notice do you give before taking planned leave? Do you have an associate VA who covers emergencies if you are unwell, or do we pause work during that time?

5. Culture & Communication:

What will working together actually look like? Beyond the logistics, you need to make sure your working styles click. Remember, your VA is not an employee. They are working WITH you, not FOR you.

  • Communication Channels: Do they prefer communication via WhatsApp, Slack, email, or a project management tool like Asana? And does this fit your style?

  • The Onboarding Process: A great VA won't just tell you to send them work. They will have systems and questions of their own to learn your business style, aims, preferences, and systems. It won’t be onerous, but it should be enough that they can work in the way you want.

Ask them: What does your onboarding process look like? How often will we do strategic catch-ups to ensure everything is running smoothly? For quick questions or do you prefer a phone call, message or email?

Now What?

The right Virtual Assistant won't blink at these questions. They will treat your business with the same respect as they treat their own and they will totally understand your need to know the details to enable you to feel comfortable.

And if you ask a question that they don’t have an answer to, do not discount them immediately. If they say “that’s a great question; let me clarify an answer and get back to you,” let them do that. That’s a professional and proactive response and shows you that they are open to getting things right for both for you. (And it’s much better than them fluffing an answer to bluff their way through the conversation).

And finally, don’t be surprised if your VA has some questions for you too. They will want to check that they are the right VA for you and your needs. It’s a partnership and, done well, can be a real game changer.