Working with a Virtual Assistant: Common Problems and Issue Resolution

Working with a virtual assistant is one of the best ways to get the time you need for business-critical tasks. However, you should be aware of the very real possibility of running into issues with your VA. Fortunately, these virtual assistant problems can be avoided or dealt with quickly if identified early in the process.


Just like working with an on-site employee, working with a virtual assistant isn’t always easy. Various issues can arise when you’re working with someone you can’t interact with in person.

The best way to avoid virtual assistant challenges is to find the right VA. This is someone who:

has the skills and knowledge your business requires, and is well-equipped with the tools and mindset for remote work.

These are some of the most common virtual assistant problems new clients encounter:


Contrary to popular belief, one of the biggest benefits of working with a VA is the time difference. A remote worker on the other side of the globe can get things in order as you sleep so that everything is ready for you when you start your workday. An eCommerce business can take calls and accommodate inquiries 24/7 without you having to work past 5 PM.

However, there are also some disadvantages to having a significant time difference. For instance, some clients forget that virtual assistants are not mere robots who can work for 16 hours a day without sleep. They are human, and if you’re not mindful of their working hours and insist on working with them on your usual schedule, it would result in burnout for them.


When you’re not working with direct employees and have limited visibility, it can be difficult to clarify their job’s exact nature and scope. You might not realize that your virtual assistant has had to take on a wider variety of tasks than initially assigned. It can get out of hand when you have someone doing things that were never agreed upon. This can easily lead to burnout, disagreements, and a virtual assistant terminating their contract.


Because virtual assistants work remotely, it can be difficult to figure out how productive they are. You might trust them yet still feel uneasy about what exactly they’re accomplishing each day. This can lead to micromanaging, which can make your virtual assistant feel uneasy and demotivated.


Communication is probably the biggest challenge you could encounter. A VA who does not communicate well creates many headaches, including delays in work and loss of important information. Without clear communication channels, both clients and virtual assistants are more likely to become frustrated. When this happens, both sides become unable to collaborate, and work quality can drop.


One of the most common virtual assistant issues encountered by those new to remote outsourcing is that their company culture doesn’t take remote workers into account. When this happens, their VAs end up disconnected and unable to participate in company endeavours. Virtual assistants have to keep up with company issues, and if they’re not integrated into the team, you risk them feeling left out.


Some virtual assistants stay with your business for a long time; others do not. There are several reasons why virtual assistants may terminate. However, now that remote work has become more commonplace, virtual assistants are in high demand, and a highly skilled VA can easily find better business opportunities. Losing someone who has become integral to your company can be devastating to your business.


Here’s how you can fix or prevent the most common virtual assistant problems:


Virtual assistants can work while you sleep or when you’ve already logged off work. This means that they can help you and your business be more productive than people in the same time zone as you. Instead of seeing the time difference as a potential issue, look at it as an opportunity to get more done in less time.


If you want virtual assistants to do your work for you, it’s important to define tasks right down to the smallest details possible. Otherwise, there will be room for misunderstanding and scope creep.

To avoid scope creep, create clear guidelines for your virtual assistant, including the extent of their work, the KPIs (key performance indicators) and metrics they need to report, when each task is due, and the timelines for each project. Be as specific as possible while still leaving room to change the details if necessary. BUT bare in mind that Virtual Assistants are Self-employed and work WITH you NOT FOR you.


A common reason behind virtual assistant problems is a lack of communication. While virtual assistants work independently, they should still be able to communicate with you about potential problems, solutions, and questions. A VA who’s not getting the guidance or feedback she needs will get frustrated, and her work will suffer.

Regular communication, whether through calls or instant messaging apps, is vital. This is especially important in the early days of a contract. Agree hours during which you and your virtual assistant are available for calls. Schedule a regular weekly meeting for quick check-ins on progress as well as on general wellbeing.

When VAs contact you with a problem, try to find out why they’re having the issue before jumping to a solution. This will give you and your VA a chance to troubleshoot solutions together and understand any underlying problems.


Make it clear that remote workers are part of the team. Invite them to engage in non-work banter, virtual happy hours, and other social events with your team.

Incorporate virtual assistants into the workflow from the beginning. Instead of treating them as second-class entities, integrate virtual assistants into your team’s processes as smoothly and intuitively as possible.

Use a project management system to help both on-site and remote team members keep track of projects and have easy access to information.

Make sure virtual assistants receive recognition for their contributions, just like on-site team members.

Virtual assistants work best when they understand their role in your business, so make sure that’s clear by including virtual assistants in your team’s regular team meetings or sending virtual assistants weekly reports on company activities.


One of the biggest hesitations business owners have about hiring a VA is how tenuous the relationship seems. Another is the time and effort it might take to build a working relationship beneficial for both parties.

But it’s really not that difficult to nurture the relationship once you make your virtual assistant a vital part of your team. 

As virtual assistants become an integral part of your business’s activities, build in regular check-in times to have conversations about the progress they’re making and how they think things are going. 

One of the best ways to show your appreciation for your VA’s hard work is to pay on time but you can also provide incentives such as a performance bonus or gift card. This will show virtual assistants that you value the job they’re doing, and any incentive increases their level of dedication to your organization.

Build a culture of appreciation, and remember to be genuine and specific in your expressions of gratitude.


The VA industry is booming, and any entrepreneur can find a virtual assistant for almost any task with just a quick Google search. However, not all virtual assistants are created equal, and if you’ve never hired one before, you can end up losing instead of saving time and money.

Here are a few tips to keep in mind when hiring a virtual assistant for the first time:

Avoid virtual assistants who claim to be good at everything. It’s better for individual VAs to focus on one area and do it well than attempt something beyond their skill level. Though Agencies will often offer a wide variety of services.

Research the virtual assistant’s background and experience to learn about their qualifications. 

If you don’t have much experience working with VAs, it can be tempting to hire based on the hourly rate rather than the level of skill and ability. Don’t fall into this trap. Instead, base your decision on the results they have achieved for previous clients and how well you ‘click’ on the discovery call.

Ask for testimonials from previous clients so you can assess each VA’s skill level.


 If you’re feeling overwhelmed by the day-to-day tasks of running your company, hiring a VA might be one of the best business decisions you make. But before making that decision, there are some things to keep in mind about working with a VA so as not to encounter any virtual assistant problems. Keep these best practices in mind to avoid the common pitfalls and overcome the challenges of working with a virtual assistant. 

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