The 4 Big Mistakes Entrepreneurs Make when Hiring a Virtual Assistant

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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With 14 year’s experience in Real Estate, 7 years running businesses, 6 years running offshore teams and importantly the Managing Director of a Real Estate Specific Offshore Staffing Solution for the past 3 years. Stephen Atcheler is an expert in helping businesses implement offshore solutions to help them scale, reduce internal wage costs, create automation and develop an online footprint.


Stephen Atcheler

The Marketing Manager and Coordinator of ShoreAgents, Angie Dayrit has built her career in the Marketing field for 5 years.
Since the early age of 20, she has been exposed to the positivities and possibilities of top career industries.
She’s a firm believer of the power of out-of-the-box thinking–taking in the key things of traditional marketing while openly embracing the technological advancements of Marketing.


Angie Dayrit

CIPS, TRC, Founder and Managing Director of property management business solutions company ireviloution is an international real estate identity who has coached, mentored and trained over a thousand of property management teams and business to success and thousands of individual property management business owners and property managers worldwide.

Jo-Anne Oliveri

A co-founder of LockedOn – a powerful, easy-to-use real estate CRM platform that makes listing and selling simple. With over 15 years in software development experience in the real estate industry, Iain has helped create software solutions that have enabled thousands of agents create lasting relationships with their customers.

Iain French

He is the Founder of the hugely successful Offer Management Platform, Market Buy, and a career real estate agent spanning 22 years. He has worked in all facets of real estate and has won many awards over the years for Innovation, Sales volume, and office performance. Dave is dedicated to improving the real estate industry and providing agents with the tools they need to survive and thrive in an ever-evolving business environment.

Dave Stewart

She is the founder of Rent Roll Starter and specialises in helping independent real estate agents to start and build their own Rent Rolls, using affordable (and sometimes free) marketing and growth strategies.

Ellen Bathgate

He is the Co-Founder and CEO of the Melbourne-based proptech start-up Rental Heroes. He is passionate about applying innovative digital solutions to help people connect better. Like many Australians, Ben and his co-founder Dom, have been both tenants and landlords. They founded Rental Heroes because they saw an opportunity to speed up issue resolution and automatically handle common tenant requests 24/7 (everything from a broken dishwasher a to pet requests!). Rental Heroes have launched their AI-chatbot “Alex” - who helps property managers by liaising directly with tenants to handle everyday requests and issues.

Ben Burton

With more than 15 years experience as a professional real estate photographer, Brad has a deep understanding of what it takes to showcase a home in its best light. After photographing homes all day and editing them all night, Brad decided to create, which has become the ultimate photo editing portal for everyone from professional photographers, real estate agents, to property managers.

Brad Filliponi

With extensive digital experience spanning over 30 years, He is a full-service mobile marketing business specialist and chatbot ninja. Mike helps empower small business owners and real estate agents to achieve marketing success on Facebook by generating leads through conversation.

Mike has built the marketing platform and designed the Facebook strategy using old school systems so that Real Estate Agency owners can build the most effective marketing lists as well as own the data from advertising and marketing. Following Mike’s vendor paid 12-point strategy over 12 weeks will build a list of over 1,000 prospects segmented into Buyers and Sellers that teaches Facebook who should see your ads in the future.

Mike Hillsdon

A marketing consultant, writer, and a social entrepreneur. For the last two years, he’s been engaged in Australian real estate marketing, media broadcasting, and shared services marketing.

He has a great passion for evolution in terms of learning which develops a holistic facet in his personality.

Ejay Manalansan

Sarah has emerged as a highly sought after speaker and panelist on the intersection of artificial intelligence and human systems in real estate. Sarah is passionate about helping agents and organisations to understand this new technology, simply, so they can make confident and informed decisions about how to adapt to a future of work where human and digital resources collaborate.

Sarah Bell

Joel is the founder of Property TV and has worked with some of the most innovative companies in Australia, USA and Europe. He is the former CEO of Californian PropTech entity Transmit Data and former CIO for a Silicon Valley technology incubator, Joel has been at the forefront of property marketing and technology for the past 15 years. Joel is also the former CIO of the Australian Property Institute and former Head of Technology for real estate franchise group, Raine & Horne.

Joel Leslie

He is a mental skills & mindset coach, and founder of  Jet Xavier Consulting Agency. Jet Xavier has conducted over 4000 elite human performance coaching and training sessions with various real estate agents and major agencies across Australia and overseasHe is a pioneer in the Real Estate industry as his training and coaching techniques bring the latest neuroscience, positive psychology, and elite human performance models to agents and principals helping them to create success at every level.


Jet Xavier

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