All you need to know about working with Virtual Assistants

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As with any employee, especially when leading a team is new to you, a variety of challenges can pop up when you add a virtual assistant to your team. Yes, the virtual environment presents a different set of circumstances than that of an in-house team. However, contrary to what seems to be the widespread belief, most of the challenges encountered are related to things like your mindset, your systems, and how you handle mistakes, rather than having something to do with the fact that the work is being done virtually.

Lucky for you, you have us to walk you through common challenges and how to overcome them! Plus, as you’ll see, if you follow the rest of our advice about investing time in creating your systems, training your VA, and so on, you will mitigate the number and intensity of these challenges.

Challenges with Your Mindset

The one thing that’s probably most likely to trip you up is your own leadership mindset. This is a good news/bad news situation. The bad news is, you’re likely to get in your own way.  The good news is that you are in the driver’s seat when it comes to eliminating mindset as a challenge in working with your virtual assistant – at least you will be if you take our advice and face the mindset challenges head-on! 

We encounter the leadership mindset blocks below with our clients all the time. And it doesn’t matter what kind of business owner we’re working with. These issues seem to come up for everyone – and our leadership team at The Virtual Hub would confess that we’ve been there, too!

It’s Quicker or Easier to Do It Myself

The number one mindset block we hear is, “It’s easier to do it myself.” So let’s be honest. Much of the time that statement will be true because it’s your business, you’ve been doing it yourself for quite a while, and you’re therefore a whiz at it. But it’s time for some tough love. If you keep doing everything yourself, you will never move your business to the next level. Period. 

Yes, it’s quicker and easier for you to do it yourself right now. But over time, it’s going to hold you back, and with proper training, your VA will soon be expert at it, as well. In fact, they may eventually be even quicker and more talented at certain tasks because they’ll be more focused on them than you can be within the whirlwind of managing your entire operation.  

Plus, even if it does take a little bit longer for your VA to do it, but their hourly rate is significantly less than yours (which it certainly should be!),  it’s more cost-effective, both financially and mentally, to delegate it to a VA. So learn to let this one go!

It Might Not Be Done Right if Someone Else Does It

Like the last one, this mindset block trips people up because it’s also true, at least at the moment. And no matter how well-prepared you are, with your systems and tasks lists, you will face a time when you’ll give a process to your virtual assistant, and it won’t quite go right the first time. But this is why you, as the business owner, take responsibility for oversight and provide constructive feedback to your VA. Over time, your VA will learn exactly how to perform tasks to your specifications – and they will be off your plate, giving you back time to spend in your genius zone. So pushing through this mindset issue when it comes up for you will be worth it to you in the long run.  

Plus, mistakes can be gifts to your business. We don’t mean to leave you hanging, but we dig into that in another section, below!

I Don’t Have Enough Time to Set It Up Right Now

This one is a classic mindset block! We hear all the time, “I just don’t have the time to get a virtual assistant up and running,” or, “Setting up for a VA will take me more time than I have right now.” And we’re not being snarky when we reply that, if you don’t have time to get a VA set up and running, then you don’t have time to grow your business! (Okay, maybe a little bit snarky.) 

You simply have to bite the bullet and create the time and space, or you are going to stay running in place forever. No matter how hard it may seem, especially during the first month, you have to move past this mindset block and find a way to invest the time in bringing on a VA. Just trust us on this one. This block will keep you stuck, but the time that you spend now to set up your VA is an investment in your time that will come back to you – with dividends – later.

It Will Take Too Long to Explain It

This one is sort of a corollary of the previous mindset block. Maybe you’re prepared to take the time to create the systems and processes, but it’s the ongoing training and oversight that feel daunting and time-consuming to you. Sure, you’re going to have to not only do the process mapping but also train your virtual assistant on the processes. And, yes, it’s not going to be a “one and done” situation, where you explain it once, and your VA performs to perfection. It takes time. 

But, as we said above, the time you invest now will come back to you, which will allow you to propel your business forward. If you don’t take this step and invest in a VA, it will paralyze you and your business. Let go of this idea ASAP!

I Can’t Trust that Someone Else Can Do It Properly

Put your hand up if you’re a control freak. If your hand isn’t up, you’re likely lying to yourself. (Or maybe you’re reading this in a public place and you’re just trying not to look ridiculous.)  

As entrepreneurs and business owners, we tend to be natural control freaks. It’s also usually why we are successful – because we care deeply about our business. To help you get through this block, really bring your VA into your vision and get clear with them on what success looks like. 

And just resign yourself to the fact that a thing or two won’t be done properly the first time. But you can use the instance as an example to go back to with your VA to explain exactly what is needed for success and what success looks like to you.

I Will Lose Control of It All If Someone Else Does It

Another control freak problem is behind this mindset block. But the paradox is that if you are doing everything yourself, it means you are out of control now. You think you’re in control, but you’re not. Needing to do everything means that your business is controlling you and not the other way around. What really gives you control? Delegating effectively and communicating successfully.  

Something amazing happens when business owners let go of this mindset block, add to their team, and learn to delegate like – well – a boss. They end up feeling unbelievably in control of their businesses even though they’re not actually the ones doing all the work. When you become the one who is overseeing the business and leading the ship, it’s an amazing feeling. Does it take work to get there? Yes, it does, and it’s not going to happen immediately. But please believe us when we implore you not to let this block stop you!

Letting Go and Moving Past Mindset Blocks

In the short term, it may be a bit tricky to push through the blocks, especially when there will be evidence to support your belief in them (e.g., your VA makes a mistake). But the long-term gains of getting through these blocks are astronomical. When you take a leadership position in your business, it can grow and grow and grow. That means becoming a true leader by establishing the right systems and processes and recruiting the right team. This is how people grow scalable businesses, and can grow and scale multiple, 6- and 7-figure businesses. If you’re wondering how the heck they can do that, when you can’t stop spinning your wheels in one business, leading a team is the secret. If any of these blocks are resonating with you, know that you are not alone. Nearly everyone experiences at least one of these blocks as they grow their business and their team. But these beliefs will paralyze your ability to grow the business that you truly want. So when you see these blocks come up, and you feel them in your head and your heart, know that you’re not alone but push through them. Repeat to yourself, “This is a leadership block and it’s keeping me stuck.” And then keep going!

Challenges with Communication

Communication is going to be the key to accomplishing anything and to the success or failure of your work with your virtual assistant. In the sections about preparing for bringing a virtual assistant on board and managing their work, we described best practices for communication in detail. Knowing when and through which channels you’ll be communicating throughout the day or week helps to manage expectations and workflows. Creating clarity around communication preferences and documenting everything in your project management tool ensures that you are on the same page and up to date with one another. 


If you establish and maintain an effective communication rhythm, you will experience far fewer communication challenges than if you don’t stick to a solid plan. But even the best-laid plans run into issues, so here are some additional ways to ensure the effective communication required for the virtual environment.

Lack of a Company Culture

But there’s a little bit more to it than having a clear meeting and reporting structure. You, as the business leader, must also maintain an open channel of two-way communication. Communicating with your VA shouldn’t be a one-way street, where you assign tasks and they merely complete them and report results. Your VA should be comfortable coming to you with problems or roadblocks and even ideas of their own. 


Establish a nurturing environment of mutual trust with your team by creating communication channels where everyone can share openly and honestly. And nurture your relationships with your virtual assistant or team by communicating beyond the needs of the business. Spend time getting to know one another, as you would in a brick-and-mortar environment. You may even want to slate some “social time” on your calendar from time to time. When you build a strong relationship with your team and communicate frequently, team members are more likely to share and contribute, which builds trust and cultivates creativity and innovation. 


Other behaviors that cultivate trust and open communication include discussing business values (e.g., respect, reliability, and honesty), listening to one another, and focusing on consistency in communication. Also, make sure your task management tools are transparent so that everyone can see who is working on what. Even better, acknowledge everyone’s contributions to the business routinely during weekly and monthly meetings.  


Don’t let the virtual environment prevent you and your team from having a clear company culture – create one. 

Not Being Clear About Who Does What and by When

Some of the tasks you assign to your virtual assistant may have a collaborative element. That is, you both need to have your hands in part of the process. For example, say content management and scheduling are tasks you want to hand off to your virtual assistant, but you continue to be the content creator. In order for your VA to successfully complete their tasks, they need to get the content from you and in a timely fashion. Make sure you are clear on how long the VA’s portion of the task will take and you give them your content with ample time to complete their steps by your desired publish dates. And don’t guess or assume. Know how long it takes your VA to complete tasks rather than assume it will take them the same amount of time as it might take you.


Now, if you’re reading up on virtual assistants because you intend to hire your first team member, this next bit isn’t relevant to you just yet. But for anyone who has more than one person on their team, be sure to assign tasks to specific individuals. We’ve heard of cases where the business owner is going to be out of pocket, so she emails the team, asking them to complete X, Y, and Z while she’s out. But she didn’t specify which team member was to work on which tasks. Without that clarity, each team member is likely to assume that the other team member(s) are completing the tasks, and therefore, no one gets the work done! And it’s not their fault. It’s up to the leader to be clear when delegating work.

Feeling Like You Don’t Know What Your Virtual Assistant Is Working On

If you follow the advice about how to map out clear, step-by-step processes, use a project management tool, and nail down a communications rhythm, you’re unlikely to be in the dark about what your virtual assistant is working on. However, it still comes up all the time – business owners feel a sense of uncertainty around their VA’s work.


Let’s just say it one more time: provide clear tasks and deadlines – using your project management tool – and keep the communication channels open, and you can avoid the doubts some business owners experience when it comes to their VAs. 


But, in addition, have reasonable expectations around how much time tasks take for your VA to complete, and remember no one is on-task every minute of every workday. So, for example, if you know one of your VA’s tasks would take you 15 minutes to do, allow them 30 or so minutes to complete it. That is, double or even triple the amount of time you would need – at least at first. It’s a cinch for you because you’ve been doing it all along, but the task is new to them. 


Finally, keep in mind that everyone needs breaks throughout the day – to grab a coffee or water, to run to the bathroom, to eat, or even just a time-out now and then to give our brains and eyes a break from the computer. In a shared, physical work environment, you wouldn’t expect someone to be tied to their desk all day, so don’t expect it because your work arrangement is virtual. On the whole, remote workers are more productive, anyway, so the amount of downtime during your VA’s working hours is likely to be far less than what you might expect in a face-to-face setting. 


If you’d like our thoughts on why business owners may not know what their VA’s are working on and what to do about it, tune into The Virtual Success podcast.

Challenges with Geography

Okay, so geography, per se, isn’t really the problem. The challenges your relative geographical locations have to do with the time zone and cultural differences that may exist if you opt to hire an offshore VA – which we highly recommend you do.  Although many business owners may see these differences has huge obstacles to working with an overseas VA, we barely see these as obstacles at all.

Time Zone Differences

If you want to be able to communicate with your virtual assistant in real-time throughout your workday, or if you need for your VA to interact with customers during your working hours (e.g., replying to issues via email), you may think that an overseas VA is out of the question. However, because being a virtual assistant is a highly desirable job in various parts of Asia, many VAs have chosen to work during non-traditional hours in order to accommodate their clients. So, you have a high probability of finding a qualified overseas VA who is willing to work during your operating hours. 


On the flip side, residing and working in different time zones is something you might want to leverage for your business. If you…


  • Don’t feel that you need to communicate with your VA several times a day
  • Would prefer not to be pinged with questions throughout the day 
  • Want to extend your hours to improve customer service, or
  • Like waking up to completed work…


…then a virtual assistant working opposite your hours might be just what you’re looking for! 


Plus, there are so many tools for communicating with one another, such as using Loom to record screen-sharing video demos, that syncing your schedules may not be essential. Just make sure that there is some overlap or that the two of you can adjust your hours so that you can have the face-to-face video calls you’ll have as part of your communication rhythm. We recommend having at least two hours of overlap with your VA in your daily schedule to ensure clear communication and productive workflow. 


Time zones can be an obstacle, but they don’t have to be! There are plenty of ways to be successful with a VA in another time zone.

We have weekly all hands-on meetings and we alter the time each week so that people in different time zones can rotate each week and attend the meetings.  We try to rotate one-on-one (meetings) constantly with the team.

Kevin Garber, ManageFlitter CEO

Cultural Differences

In our digital era, the world has become a much “smaller” place. With virtually unlimited information and entertainment available 24/7, we’re all exposed to more and more diversity every day. Basically, people around the world are getting more familiar with each other.

Also, in the countries where the virtual assistant industry is rapidly growing, such as India and the Philippines, English as a second language is very common and many are highly proficient speakers of the language. In fact, the Philipines has two official languages: Filipino and English. (The Philipines is fourth, behind the U.S. India, and Pakistan, in its number of English speakers!) 


And as far as Filipino culture goes, it’s a blend of both Eastern and Western influences, so its citizens have a lot more in common with Westerns than you might think! So cultural challenges in working with offshore team members, especially those in the Philippines, are becoming less and less of a challenge over time.


With certain exceptions, which we covered in the ‘how to hire’ section, any challenges in working with a team member from a different culture can be easily overcome with the right mindset and open communication. 

Business Security

A common concern when it comes to considering a virtual assistant is how to grant access to the business systems the VA will need to use while still protecting the security of the business. It’s a legitimate worry, as you won’t really know and trust your virtual assistant (at least at first!), yet you’ll need to allow them into the systems and information about your business. Of course, you could say this about any new employee, virtual or otherwise, yet it seems to create much more fear in the virtual environment. 

Virtual assistants are likely to be honest. Otherwise, they’re not going to be in the industry for long. At the same time, just as a brick-and-mortar business might limit access to certain programs and software, it’s savvy to have some protections in place, if for nothing else than your own peace of mind. Fortunately, there are many ways to reduce the risk involved and protect your business. Let’s take a look.

Develop Clear Data Security Policies

If you’ve been working solo or with a small local or familiar team, you’re not likely to have already developed policies around security (or maybe much else for that matter!). It’s pretty common sense for employees, including VAs, to grasp their need and responsibility to protect your data, but it’s smart to have a policy and to make your expectations clear and specific 

As you’re documenting your business processes, add a policy for data security, information privacy, and anything else that might be relevant to the security of your business.  Also, as your recording and documenting tasks you’d like to hand off to your VA, think about what access they’ll need to perform each task. Some programs have levels of users, where some users have full access to all capabilities, while others can perform limited functions within the platform. Within systems like that, you can block access to anything they don’t really need.

Make sure you keep a record of what your VA does and does not have access to so that it will be easy for you to recall what they can access, as well as to change settings or otherwise take away access should something go wrong.

Look at Business Security Systems Options

Sometimes business owners aren’t aware that there are alternatives to giving providing their virtual assistant with their own login credentials for their accounts. For example, they share give the VA their own username and password to their business website, allowing the VA to essentially log in as the business owner. 

The trouble with giving away your logins and passwords is that the VA has that information, and you’ll be scrambling to change them all should something go wrong or your VA moves on to another opportunity. (Think of what a pain it is when you try to log in to one of your accounts and you have to reset the password because you forgot it or because the software forces periodic updates. Now imagine that times all of your passwords!) Also, your login will include complete administrator access to any system, and that’s not always ideal. 

For every one of your systems, you’ll give the VA access to, provide them with their own username, being sure to look at the user options you can assign to their access. VAs should definitely have their own accounts, and it’s preferable if you set up those accounts so they are restricted to only the functions the VA needs to get into. For example, Facebook has several options for page roles, including administrator, editor, moderator, and analyst, and each has things they can and cannot do. It will be much simpler and safer to simply revoke access or delete an account in a system, rather than having to update all of your passwords. 

In many of these tools, having unique user IDs means that you can also track what other users do in your software. You can see if they appear to be doing anything that is not within the scope of their job. 

Another point here is to look at tools or software which include version control with them. Version control allows you to see what has changed and to revert to previous versions at various points in time. For example, both Microsoft Word and Google documents allow you to view earlier versions of documents.

Use a Password Manager

For any tools where you can’t create a separate account, or where the work simply requires the VA to go in “as” you, you should use a password manager, such as LastPass. Password managers allow you to grant access to your online systems – from social media platforms, CRM and project management tools, to your business email accounts, and your cloud storage drives – and log in as you, without giving them your passwords. A password manager like LastPass stores your username and password combinations safely in your app account. When you want to revoke access, you simply go back into the sharing feature within your password manager and withdraw it.


As a bonus, LastPass will tell you when your passwords are weak, it will detect when you’re using the same credentials on multiple platforms, and it will suggest and manage those super secure passwords that are basically random assortments of letters, numbers, and symbols!

Use of Credit Cards

If you want to have your virtual assistant place orders or book events, you’ll have to provide them with a way to make payments. However, you should never hand over your credit card details for a variety of reasons.


For one, the fine print of most credit card contracts includes conditions that nullify your fraud protection if you have shared your details and experience fraudulent transactions. That means that even if your credit card is stolen – and the fraudulent charges weren’t made by your VA – the credit card company can stick to their fine print and not investigate and reverse those charges!


If making payments will truly be a routine need for your VA, you have some alternatives, including:


Getting them a card, in their own name, on your business credit account.

Nominating your VA officially to have access (you’ll need to check with your provider as to whether they will allow this. Make sure they know the VA isn’t an employee where they are a contractor or hired through a third-party company).

Getting a prepaid card just for the VA’s use, which will automatically cap what they can spend.

Granting them access to a card with limited available credit.

Use Copyrights and Patents

If you’re created proprietary tools, systems, and branding, protecting your intellectual property is likely to be of importance. As such, it’s a common concern, as a VA will often gain intimate knowledge of the inner-workings of your business. It’s therefore important to take steps to protect your intellectual property through copyrights, trademarks, or patents. This at least gives you a paper trail and some legal footing should you need it later. 

Keep in mind that, when you’re working across international borders, enforcing intellectual property claims is always easy or effective. We recommend speaking with an attorney who’s qualified to speak to intellectual property law, as their application often depends upon the country that you live in. 

Overall though, if it’s something that you qualify to have, it tends to be better to have security policies like this than not.

Use Non-Disclosure Agreements (NDAs) and Non-Compete Clauses (NCCs)

An NDA (non-disclosure agreement) helps you to have some legal recourse if your VA were to share any proprietary information from your company with anyone else. The agreement basically asks them to keep your “behind-the-scenes” confidential, and not share your client lists or any other vital business information. 

An NCC (non-compete clause) is sometimes referred to as a CNC (covenant not to compete). Asking an employee to enter a non-compete agreement means they will not go work for a competitor or start a competitive business of their own when they terminate their work with you. Typically, they bar the employee from competing with you and/or working for a competitor for a finite period of time after they stop working with you. The purpose behind these agreements is to stop them from gaining a competitive advantage over you by using the intimate details of your business. 

NCCs generally last for a limited amount of time, and they may also be limited to specific geographic areas. Courts tend to uphold NCCs as long as the limitations included are “reasonable.” Asking someone to never compete with you in the future would be a limitation the courts would consider to be unreasonable.

Do Your Homework on Virtual Assistant Providers

The best security measure you can take is to do your homework before you find and hire a virtual assistant, rather than merely building in protections once they’ve come aboard. If you want to go with a freelancer – and you’re therefore hiring on your own – don’t fail to check candidates’ work history and references. 

You want to ensure you speak with people who can verify work history, reliability, and performance levels. It’s a good idea to also invest in some background checks. If you intend to search for freelance candidates through platforms such as Upwork, the candidates there will have ratings and reviews, but be aware that they can be fakes and don’t rely solely on reviews to vet a candidate. Be sure to connect with at least one real person who can speak on the candidates’ history, experience, and work ethic or habits. 

If you’re new to hiring team members, this can be a bit time-consuming and even a little intimidating. Searching for candidates through a third-party, virtual assistant company can save you a lot of legwork, but take a little time to research the VA companies you consider. Just like VAs, they’re not all created equal. You’ll want to know if the company has security policies in place to protect its clients and if they receive good reviews from their clients. Most reputable companies NDAs and contracts which bind them to information security and confidentiality rules built into their placement services, but you’ll want to verify that. You may also want to ask to see the agreements in case you have a specific clause you’d like to include. A good, reputable company will accommodate your needs. 

Another layer of security can be added when you hire through a VA company where your VA will be under the direct supervision of that company. For example, at The Virtual Hub, our VAs are all grouped into teams where quality assurance is monitored and ideas are shared. It creates an ecosystem of accountability and productivity, designed to protect clients and give them the best possible experience. 

Fears over the security of the business are a common obstacle that prevent owners who need help from jumping in and hiring a virtual assistant. And we get it. Securing your business should be a concern, but it shouldn’t be such a worry that it prevents you from getting the help that you need. By simply putting a few precautions in place, your business will generally be as safe as with a virtual team member as any business would with an in-office employee.

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