The 4 Big Mistakes Entrepreneurs Make when Hiring a Virtual Assistant

Many people have tried working with a virtual assistant, and many of those have failed. For every Tim Ferriss success story there are a dozen people ready to say that they tried it but it didn’t work.

A VA is great in theory – a low cost assistant to help clear your overflowing to-do list – but can be harder than expected to execute. There are several common mistakes that you can avoid to make your VA experience a much smoother one.

So whether you’ve tried unsuccessfully before, or whether you’re thinking of diving into the world of virtual assistants for the first time, here are the 4 big mistakes that entrepreneurs make when hiring a VA.

1. Underestimate the time

Hiring a VA is not a magic bullet. You can’t just hit ‘hire’ and then this person that you’ve never met is going to solve all of your problems.

The biggest mistake any entrepreneur makes when it comes to hiring a VA is having great intentions at first but then not giving it the time it needs. Be clear about your requirements and recruit accordingly. You may not need a proper job description, per se, but you should have a clear list of tasks and procedures. Start small and build out.

There’s no point just hiring someone because they’re cheap and hoping it’ll work out. Maybe it will! But like any hire you make, you have to think about what you and your business actually need and then choose someone based on that.

Then you have to take the time to understand how you’ll work together. There’s the basic stuff like setting up a communication style, project management software, and deadline expectations. But in the first few months, it’s unlikely that you’ll be able to simply assign a task and assume that it will be done exactly as you want. You’ll need to thoroughly outline the steps, explain the reasoning, and describe the final expectation.

This sounds time consuming, and it is. All employees deserve an induction period and that’s how you need to view this time. If you’re lucky, you’ll make a great hire who totally gets you and your vision and your business on day one. Awesome. But that person is going to be at the expensive end of the range. Which brings us to…

2. Underestimate your budget

A VA is often an entrepreneur’s first hire, when you’ve got too much work but not quite enough budget for an employee. If budget is your main concern, then you can definitely hire a cheap VA. But remember that with every cost saving comes a hidden cost. A fresh new freelancer on Upwork will only be a few dollars per hour in theory, but they will need a lot of training, time and very clear and explicit instructions. That time adds up to dollars.

If you hire the right person, a VA will definitely save you a bunch of money. For example, a real estate virtual assistant will be a third or a quarter of the cost of a local employee. A property manager with a VA can go from managing 150 properties to 300, so for the cost of a quarter of an employee you’re doubling your productivity. Not bad.

But there are still costs involved. Too often, entrepreneurs think a virtual assistant is practically free. This is a big mistake. Plan the costings for your VA as though they are a full time domestic employee – because for the first few weeks, or until you find your perfect person, that’s realistically how much it could cost you in time and set-up.

Yes, virtual staff will mean a drastic reduction in costs to your business, but make a realistic budget at the start so that you’re not unpleasantly surprised.

3. Underestimate the management

By now you’re getting the impression that having virtual staff is not all peaches and roses. Absolutely, a virtual assistant can transform your business from one that is surviving to one that is thriving, and a key part of that is management.

When you start down the road of offshoring parts of your business, you need to be involved in the process of setting it up and managing it. You have to know how everything works together.

But a mistake that entrepreneurs often make is they wind up managing their workforce instead of managing their business. Your business is your business. As soon as you can, pass the task of people management off to somebody who will be able to drive the process, be responsible for training, and make sure the whole thing works.

A great example is Box Brownie, which is a real estate photo editing company founded by Mel Myers. Myers recognised that the success of his company relied on an excellent virtual team so he needed to invest in its management. He turned this task over to one of his local staff. It was their responsibility to filter recruits, build tests and onboard the right people and then to continue to train, grow and scale the staff. Myers got on with the business of making his company successful, knowing that someone else was in charge of his staff. That person travels to visit the offshore team regularly to make sure they feel part of the company, and also to learn more about them.

Which brings us to…

4. Underestimate cultural differences

When we talk about a virtual assistant, virtual staff, outsourcing or offshore teams, we’re talking about real human beings. The reason they are more cost effective is because they live in countries where the cost of living is drastically lower than the US, Australia, Canada, or the UK. They are usually university educated, communicate in excellent English, and are very well qualified.

That being said, you may not always understand them and vice versa. This isn’t about language; it’s about culture. You can’t take anything for granted. Your virtual assistant may be too shy to ask questions or admit they don’t know something. They may expect a lot more micro-managing than you’re used to doing, not because they require scrutiny or supervision, but because it shows that you’re interested in their work.

Just like with your local staff, you need to develop relationships with your virtual team. If you get to know them and their situations, you can avoid surprises. Many Filipino workers, for instance, are looking after extended families and may need to take days off suddenly to care for someone.

Language is important too, so avoid slang or colloquialisms. When setting out tasks, always be clear and specific. For example, what does “find me a mid-range hotel” mean to a worker living in India? It’s better to spell out exactly what your budget is.

And finally, keep in mind that they are working in a different time zone! Your virtual assistant might be starting at 4am, so cut them a little slack.


Taking on your first virtual assistant can be exciting and daunting. When you do it right, outsourcing will completely transform your business by making it more efficient, cost effective, and streamlined. But go into it with your eyes open. Be realistic about how much time, money and management you need to invest. And be open to learning about a whole new culture.





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