I was asked this question by a client and I have seen it quite often in Facebook Groups.
Short answer: When you are organized.
Long answer – keep reading…
First, Determine if You Really Need a Virtual Assistant

Entrepreneurs are often responsible for managing multiple aspects of their businesses, which can be overwhelming and time-consuming. Hiring a virtual assistant can be a smart move for an entrepreneur who needs to delegate certain tasks so they can focus on the core aspects of their business.
If you are an entrepreneur, this isn’t news to you. In fact, it should not be a surprise that you have arrived as this crossroad because you may:
- Feel Overwhelmed: If an entrepreneur feels like they have too much on their plate and are struggling to keep up with their workload, hiring a virtual assistant can help take off some of the pressure.
- Limited Time: If an entrepreneur is running out of time to complete important tasks, hiring a virtual assistant can help them free up time to focus on more pressing matters.
- Lack of Expertise: Entrepreneurs may have gaps in their skills and knowledge that prevent them from completing certain tasks efficiently. In this case, a virtual assistant with expertise in the relevant area can be a valuable asset.
- Inefficient Operations: If an entrepreneur’s business operations are inefficient, a virtual assistant can help streamline processes, freeing up time and resources for more important tasks. *More on this one below.
- Need for Growth: If an entrepreneur is looking to expand their business, they may need additional support. A virtual assistant can help them scale their operations while keeping costs low.
A Virtual Assistant (or a Online Business Manager who also executes tasks instead of delegates) allows you to pass the proverbial baton, providing the opportunity to:
- Save time and Increase Productivity: Not only is a VA helping you with the time you already confirmed as being limited, they can provide attention and focus to projects that may be great for your business but not worth your attention at the moment. Depending on the VA hired, they may also have less obligations monopolizing their time, allowing them to dedicate more time and energy to your business – moving you forward at a pace you wanted but couldn’t achieve on your own.
- Reduce stress by improving work-life balance: A VA can take care of some of the tasks that are causing you stress, so you can relax, enjoy your work, and maintain a better work-life balance, spending more time doing what you love (instead of being glued to your phone, computer, or drowning in a sea of to-dos).
- Facilitating the growth of your business: It is rare that a VA only has one client – meaning they have behind the scenes knowledge of what others are doing within their business. While they should not be sharing trade secrets, they are gathering additional skillsets and trend knowledge that can be implemented into your business, helping it grow and scale outside of your abilities.
Next, Determine If You (and Your Business) is in Good Enough Shape For a Virtual Assistant

While the list above sounds ideal, it is important to understand a Virtual Assistant is an extension of you.
While they can do A LOT, Virtual Assistants are not magicians, do not have pixie dust, or access to magical wands (to my knowledge). They can’t make peace out of sheer anarchy without some type of direction and a solid foundation.
Simply put, if you aren’t organized, how do you expect them to be able to help you?
If you have been running around not knowing the sky from the ground, bringing someone else in is only going to add to the chaos – more questions, more confusion, more frustration, more things to do, more stress.
It is a common misconception that VAs and/or OBMs are there to help you get organized. Yes, some put that in their job title but let’s be realistic, unlike a disheveled closet or junk drawer, each element of our business is a source of income. If an individual comes in slinging suggestions without understand how it all works, they can do more harm than good.
The one exception is if you are doing a complete revamp, throwing most, if not all existing policies and procedures out the window and starting anew. If that is not the case, the new proposed method will clash with the tried and true way of doing things, creating friction and frustration between you and the VA. The ideas implemented are only as resourceful and helpful as the person using them. Save yourself and your VA time by figuring out your business model, workflow, then get their input.
Now, How to Know You Are Ready to Hire a Virtual Assistant and How to Select the Best Fit

Once you have your business organized in enough of a manner that you know what is sacred and should not be touched, are able explain the processes in place so the VA has a clear understanding of how your business works, and you can give them the keys to the house without the fear of them burning it down – you are ready to hire a VA.
First: The Ideal Match
It is important to understand that the term Virtual Assistant is broad and the tasks they can accomplish will depend on what they offer (another reason to be organized – ensuring who your hire is able to do what you need). Once you know what tasks you need help with, you can start looking for a VA, aligning their skills with you needs.
If you jump in feet first and hire someone simply because they were recommended or because they were affordable, you may find yourself floundering or stuck in a contract with someone who is only adding to your stress, not taking away from it.
Again, take a moment – make a list, determine what you really need for your business, what you would like done in your business, and and out of those two lists – what skills are a “must have” and are “recommended, but not required”.
Second: Trainable or Already Prepared?
The next thing is to determine if you have the time (and energy) to train a VA. Are you meticulous with how your business is ran? Can you loosen your grip on the reins to let someone come in and take over, doing it their way or do you need them to be your carbon copy – not venturing outside of the lines you have drawn for them?
If you don’t have a lot of time to train a VA, you might want to consider hiring someone who is already familiar with the tasks you need help with and can take action with minimal direction and feedback.
Third: Can You Afford the Additional Help?

Say it with me – cheaper IS NOT always better. You get what you pay for?!
I have lost count of how many clients I have onboarded because they have been ghosted by a VA with an hourly rate equivalent to a Starbuck’s coffee (sorry Massachusetts – Dunkin Donuts Coffee). To each their own in terms of their rates but I will let you in on a secret – the hourly rate is equivalent to the tolerance level – especially if you have the skillset to back it.
While VAs overseas may charge substantially less than those in the US, everyone has a line in the sand and if you cross it, nothing is worth continuing the relationship.
I say this because if you are a difficult person to work with (yes – no one is willing to admit this to themselves – I get that), going for a lower rate individual will leave you searching for someone else before the ink dries on the contract.
It’s also important to be aware that someone with a lower rate may just be SAYING they can do it as again, I have seen in countless Facebook groups someone who just obtained a new client quickly seek advice, training, and/or guidance because they have no idea what to do.
Dare I say it – people will lie.
It is messed up but for those starting out, coaches are giving them this advice. “Fake it ’til you make it”. “Get experience by any means necessary”. “Close the sale and figure out the rest later”.
The point to all of this is that knowing what you want to spend is going to play a strong role in when you hire and who you hire. If you are indifferent about the outcome and would rather keep your overhead low and hiring within a budget, you are welcome to move on to the next section.
If you find that quality beats cost and you would rather hire for a slighter hire rate where experience can be proven, then feel free to revisit this page at that time.
In either case, it’s important to set a budget before you start looking for a VA so that you don’t overspend.
Alright, I am ready to train, I know my budget, I have found a few candidates – now what?

There is nothing wrong with taking a VA for a test drive.
Sounds scandalous but hear me out.
Personalities clash all…the…time.
While the VA may be exceptional in terms of skills and just right for your budget, are they easy to work with and will they get you?
- If you are someone who is fun-loving and has a sense of humor, do you want someone who is serious and brooding all the time? Same in reverse.
- If you are a talker, do you want someone who doesn’t care for idle chit chat and just wants to get the work done?
- Do you want a worker or a partner in crime? Do you need handholding and constant updates or are you ok with radio silence until the task is done or constructive updates are provided?
If you’re still not sure, this is why it is ok for you to test the waters.
Hire a VA for a few hours on a trial basis or for an isolated project. This will give you a chance to 1) validate their skills, 2) see if they can really help you and 3) determine if you are comfortable with them.
Overall, hiring a virtual assistant can help entrepreneurs improve their productivity, streamline their operations, and free up time to focus on strategic tasks.
The right time is subjective but being organized should be the baseline of that decision.
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