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How To Successfully Work With Multiple Virtual Assistants: Top Tips For Entrepreneurs


Barnaby Lashbrooke

Founder and CEO of Time etc, author of The Hard Work Myth

8 minute read

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Working with virtual assistants (VAs) is no longer a luxury that only the top 1% can afford to invest in. More and more businesses are utilizing their services to streamline their operations and reclaim valuable time for more meaningful work.

Nevertheless, taking the plunge into the world of virtual assistance can still be a big decision for many entrepreneurs, and you want to make sure you’re getting the most out of your time and money.

What many people don’t realize is that one of the best ways to optimize your experience is to have more than one VA by your side to support you. But the sad fact is, when hiring one VA feels like a big step, even fewer people feel confident in bringing additional assistants into the fold.

Why should you work with multiple VAs?

Many entrepreneurs and business owners who come to us only consider working with one assistant when they imagine the support they’ll need. And depending on the tasks they need to offload, one assistant may well be enough.

However, if their needs are more varied or specialized, it can be difficult for one individual assistant to tick every box in terms of skills and experience needed to complete their work.

At this point, we would recommend bringing an additional assistant onto their team to make sure all bases are covered. This does not incur any extra cost, as plans are based on hours of support rather than the number of assistants. For example, two assistants completing one hour of work each is equal to one assistant completing two hours of work.

While many are open to this, some are less sure. If you find the thought of working with a larger team of virtual assistants daunting, we want to put your mind at rest. With the right know-how, you’ll be able to harness the power of your growing team with confidence and ease.

But don’t just take it from us. One of the best things you can do is learn from those who have been there and done it — in this case, people who have successfully worked with many virtual assistants for a number of years.

Tom* has been a Time etc user since 2016 and currently has ten virtual assistants on his team.

John* has been with Time etc since 2019 and has three virtual assistants to cover his different needs.

Here, you’ll find Tom* and John*’s first-hand insights on how they have maximized the success of their multiple-assistant team, along with our own tried-and-tested techniques.

Tips for successfully working with multiple VAs

Clear instructions

You and I both know that as a busy entrepreneur, your time is precious. Chances are, you want to hire a VA so you can take tasks off your plate, not add more to it. While creating instructions or handovers may seem like another low-impact, time-consuming task, Tom* says it’s a crucial step.

There’s no need for fancy fonts or excessive decoration, just as long as they are clear and easily accessible. “(Instructions) can come in any format, including video and written documents. I like to use a shared document format such as Google docs so that VAs can see the latest changes and contribute updates at all times,” he says.

“I encourage VAs to update the process docs, especially when encountering a task for the first time because it's easier for them to identify the areas that aren't clear,” he added.

By taking the time to do this, you will set your virtual assistants up for success and free up more of your own time in the future.

See: Five Essential Tech Tips For Getting Started With A Virtual Assistant

Have a “main” assistant

As busy entrepreneurs with so many responsibilities to juggle already, one of the most common fears that hold our users back is that managing multiple virtual assistants could be too confusing to keep track of.

One method we have found to be incredibly effective is to have one VA act as your “main” assistant. They can act as the main point of contact between you and your wider VA team and can be responsible for delegating to and coordinating with the other assistants—almost like a project manager of the team.

Regular communication

Even if you have your main assistant handling your additional assistants’ tasks, it’s still essential to communicate regularly with each assistant on your team.

Avoid falling into the trap of “out of sight, out of mind”. John* agrees, “In a virtual environment, greater effort is needed to make sure everyone is on the same page and working well together.”

By this, we mean that sometimes it’s hard to avoid getting lost in the day-to-day shuffle of your work, and it can happen to the best of us. But just because you don’t see someone every day, it doesn’t mean they don't need your attention. Taking the time to stay connected and engaged with each member of your virtual assistant team is vital for strong, productive partnerships, and greater success in the long run.

Findings from a recent McKinsey Global Institute report support this, too. Their results showed that teams that are well-connected are 20-25% more productive compared to others.

We always recommend scheduling regular one-on-ones or check-ins with your assistant to provide opportunities to catch up on what they’ve been working on, give feedback, and answer any questions they may have. In John*’s case, he keeps lines of communication open through “all points of contact” – email, phone calls, instant messaging, and so on – to be available if ever an assistant encounters a problem, which helps keep things running smoothly.

But the impact of good communication reaches far beyond your meetings and Slack channels. Creating an environment that encourages openness, honesty, and accountability will help build trust between you and your virtual assistants, and foster a more positive working relationship.

Don’t be strangers

Not just reserved for clients, Tom* also recommends encouraging communication within your VA team.

Introduce the different virtual assistants on your team to each other and encourage them to keep in touch. This creates a strong feeling of teamwork and collaboration and means they can rely on each other for support and questions rather than having to always refer back to you. “Email dialogue and video calls are particularly beneficial when someone is new to a task”, he says.

It can also mean that if one virtual assistant isn’t available for whatever reason, they can ask another assistant on the team to step in directly (depending on what the tasks are, of course!).

Take advantage of tech and tools

The good news is that there is no shortage of tech options and resources available to streamline your processes and make working with multiple VAs easier.

For example, many of our users utilize LastPass or Secure Share to make sure each assistant has all the right access they need to complete your tasks. Or, if you’re struggling to think of ways to use more hours in your plan, use the free to-do list optimizer on our website to find out exactly how much of your regular work should stay on your plate and which tasks can be handled by your virtual assistants.

When choosing collaboration or project management tools to use, it's worth considering a tool that's neither too complex nor too limited. Keep into account the type of work your team will do, the size of the team, and its goals. For instance, a tool like Clickup can easily become your one-point solution for many of your VAs' tasks – from project management to customer service. But if you only need a simple task management system for a small team, a free Trello account could be all you need.

Bonus tip

To make sure you’re setting yourself up for the best chance of success, John* says you must always remember the reasons why you’ve opted for a virtual assistant in the first place, rather than an in-house employee.

“(Hiring virtual team members) allows you to fish in a much bigger pool for skills and talent, and hiring a portion of someone’s full skill set to match specific tasks is usually more effective than hiring the full package (of a full-time employee) for the same task, where the rest of their skill set won’t be put to use,” he says.

Whatever your reasons for not hiring in-house, you’ll want to make sure you reap the benefits of a virtual assistant as soon as possible and for as long as possible. But this will be hard to achieve without investing some time and effort into your virtual employee, John* explains. “Companies go to great extents to onboard new employees, and for good reason,” he says. “So despite the fact that you’ll likely never meet in person, it’s important to remember that virtual assistants are still part of your business.”

See: How To Form A Successful Relationship With Your Virtual Assistant

What’s the bottom line?

Running a business is not for the faint-hearted, and the more you grow it, the more complicated things can get. As an entrepreneur, you’re probably already familiar with how valuable virtual assistants can be for helping you to achieve more. But when it comes to getting the best support for your needs, sometimes two heads are better than one. Working with multiple virtual assistants may feel like a daunting prospect, but in reality, it’s a simple step to unlocking even more of your and your business’s potential.

If you have any questions or queries about getting started with a virtual assistant, or if you need additional support, our expert team will be more than happy to help.

*Names have been changed.

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About the author

Barnaby Lashbrooke is the founder and CEO of Virtual Assistant service Time etc as well as the author of The Hard Work Myth, recently recommended by Sir Richard Branson. Barnaby is a Forbes Columnist on productivity and is also an accomplished entrepreneur, selling more than $35 million worth of services.

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