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Things that can (and do!) go wrong when hiring a Virtual Assistant


Barnaby Lashbrooke

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

8 minute read

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A Virtual Assistant can be a powerful resource to help you do more, be more efficient, and increase your earnings.

With their organizational skills, deep knowledge of your industry, and a keen ability to plan, they are an invaluable asset to your team, as long as you choose the right person for the job.

Skills and experience play a big role in how a virtual assistant fits into your team, but characteristics like personality, communication style, culture, expectations, and work style matter, too.

Over the years we've matched tens of thousands of entrepreneurs with assistants, and while it goes well the vast majority of the time, we've seen pretty much everything that can go wrong with getting a virtual assistant on board to assist you.

The most common issues are personality clashes and misunderstandings in expectations and task delegation, leading to delays and incomplete work.

These are "gotchas" that can quickly turn hiring a virtual assistant into a failure and put you back to square one and even disrupt your operations.

You'll need to start the hiring process all over again, costing you time and money.

These are especially important to pay attention to if you haven't hired a virtual assistant before—and if you have, and it didn't end well, these might point you in the right direction.

Poor match

One of the most common issues we see in selecting an assistant is not making sure the assistant you choose is well-matched to you and your business.

Start by considering which tools and systems are essential to your operations. Does your team live on Slack? Are you already managing your emails with Streak and your social media posts with Buffer? Ideally, your virtual assistant is familiar with these and similar tools or brings her knowledge of different tools to improve upon your current workflow.

However, the list of achievements in their resume is not the only criteria to keep in mind. Soft skills are just as important to succeed in any company. Qualities like teamwork, communication, flexibility, organization, empathy, and analytical skills are crucial for any Virtual Assistant. Your assistant must be organized enough to make your work more efficient, but also have the flexibility to respond well to unexpected situations.

Also, consider personality type—do you need someone more formal or are you happier working with someone relaxed? What personality types have you worked well with in the past and what hasn't worked so well? Trying to skip the selection phase and assuming it isn't important with a virtual assistant is the problem here. It's almost more important when hiring a Virtual Assistant because chances are, you'll never meet face to face.

Not investing time in or building the relationship

The second most common failure scenario is that some people don't invest time in their new virtual assistant, providing training, induction, and guidance to them and explaining how you'd like everything to be done. Whilst virtual assistants can work using their initiative, they will still need your direction and investment, especially at the start of the relationship.

Regardless of their years of experience and how familiar they are with your industry, each business (and business owner) is unique. So, your new virtual assistant will need some training to familiarize herself with the way you work. Some of your crucial operations may differ from the systems she had in place and worked for her before.

Likewise, you need to plan to build a relationship with your virtual assistant too. Sometimes people assume this isn't as important with third-party contractors like VAs or freelancers, but we would argue that it's as vitally important to build a solid, supportive, and safe relationship with your virtual assistant as it is with any new hire.

Getting to know your virtual assistant more closely and even personally (with clear boundaries, of course) is the best way to keep communication flowing, and understand their motivations and the way they work.

Unrealistic expectations

Unrealistic expectations represent a big stumbling block in enjoying a virtual assistant—from trying to delegate without providing instructions to expecting your new virtual assistant to change your life without investing time and energy into helping them do that.

Just because a virtual assistant can take on a multitude of tasks, it doesn't mean they will do the work of several people. As your operation grows, you'll need to add more people to the team to work on tasks like content creation and marketing.

Despite what you might have seen in films (think The Devil Wears Prada) expecting your virtual assistant to be a ‘mind reader' and be one step ahead of your every need isn't always realistic.

Experienced virtual assistants might anticipate some of your needs or potential issues, but it's not realistic to expect them to know what you want at all times if you don't communicate those needs.

You don't get dramatic timesaving results from your assistant unless you're prepared to invest almost endlessly in helping them achieve that for you.

Delegating the ‘wrong' tasks

A common cause of failure of a virtual assistant relationship is the delegation of the 'wrong' type of task. So delegating tasks that only you can do, or require your specific input or knowledge to complete rather than repetitive tasks that are time-wasting or you lack sufficient skill or knowledge to complete.

Your virtual assistant will be most helpful in organizing, scheduling, and prioritizing. For example, they can set up an email system to put your important messages front and center while filtering out the non-critical messages. However, most times you'll need to reply to those emails personally.

Another common mistake is to delegate critical tasks like marketing and sales to an assistant. This rarely works—especially if your business or sales channel is new—because your assistant is likely to have less passion, conviction, and knowledge than you do in growing your business.

Many virtual assistant positions are asking applicants to wear many hats—administrative tasks, personal tasks, finance management, event planning, research, social media management, content writing, email marketing, and so on. However, the more you split your assistant's time and attention into dozens of different tasks, the less time they'll have to focus on their core responsibilities.

Not treating your virtual assistant with respect

Finally, it's important to realize that you need to treat your virtual assistant with respect and consider rewarding them well to create a successful ongoing relationship that really helps you to achieve more.

Something as simple as congratulating them for a recent achievement goes a long way to ensure your virtual assistant feels appreciated. For example, if the results of their outreach efforts landed you an important collaboration, don't forget to mention their role in it when you announce it to the rest of the team.

It might sound surprising, but some people forget that their virtual assistant is a living, breathing human who needs to be treated well, encouraged, and motivated to function at their best—just like all of us.

Boundaries are paramount in healthy relationships of any kind. The way people communicate their boundaries depends on their personality and the culture they grew up in and their level of comfort at the workplace. A healthy, positive work environment encourages people to set, communicate, and respect boundaries.

One boundary you and your assistant need to establish firsthand is their schedule and availability. You shouldn't expect your assistant to be available 24/7, always on and ready to reply to every message, even on nights and weekends. That recipe only leads to burnout, poor work performance, and an unhappy employee. Instead, make sure your virtual assistant sets up a schedule accessible to you as well that reveals their work hours and the times and dates when they'll be out of reach, including weekends, holidays, and days off.

When a client doesn't take the time to do these things or, worse, doesn't treat their assistant with respect this can cause serious complications to occur including the assistant not wanting to continue working with the client.

Remember, most virtual assistants are independent and can therefore pick and choose who they work with!

See: Virtual Assistant Vs. Personal Assistant: The Best Support for Business Owners

What can you do to avoid negative situations with a new virtual assistant?

With remote work, you now have access to a massive pool of potential candidates from all over the world, but how do you make sure the person is the right match? Here's what you can do to improve your hiring process and increase your chances of hiring the best for the job on your first try.

Write a clearer job description

The job description is crucial to receive applications from the right people. Virtual assistants can perform a multitude of tasks, from administrative work to content creation and social media management, but it doesn't mean they can do it all and do it well.

So, break down your three must-have priorities and three or four nice-to-haves.

Do you need your virtual assistant to focus on admin work and managing finances? Do you not mind answering your email but need someone to support you with community management and content creation?

Now that you know what your virtual assistant's primary tasks will be, start writing your job ad. Being with a company summary describing what your company does and some of your core values. Then, describe the benefits your offer, followed by the requirements of the position and the main tasks you just determined.

The more specific your job ad is, the easier it will be to catch the eye of the best applicants.

Ask the right questions

After narrowing down the candidate pool to a handful of applicants, you can start scheduling interviews. These are crucial to getting to know the candidate better and assessing other skills not easily seen on a resume or portfolio.

Above all, ask questions that evaluate their previous experience and how they'd apply it to their new position.

For example, here are a few common interview questions to evaluate your applicants:

  • What do you consider to be your major strengths and challenges?
  • What's the first thing you do when you are assigned a new task?
  • How do you handle a disagreement with a colleague? And a disagreement with a client?
  • What does success look like to you?

Your computer breaks and you're on a tight deadline. What would you do to make sure all parties are notified and get the job done on time?

Pay attention to company culture

All companies have a culture, even if you are an entrepreneur. While big companies have brand and company manuals, that's not always the case for entrepreneurs and small businesses. It doesn't need to be a big document, but explaining what your business's mission and vision are, what lies at the core of what you do, and what matters to you, to your team and your company will make all the difference to ensure your virtual assistant fits right in.

Notice their communication style

A crucial aspect of any professional relationship is communication, and it begins with onboarding people who share similar communication preferences.

Again, before starting the hiring process, make sure your own communication style is clear to you.

How often do you like to give and receive updates from your team? Which tools do you prefer to stay in touch with them? Do your teams work together more often or are they free to work independently?

Onboarding a virtual assistant with a compatible communication style ensures your operations run smoothly.


  • Hiring the right person is crucial to your operations, giving you the time you need to focus on more demanding tasks and increasing your efficiency and productivity.
  • Finding the perfect virtual assistant for your company isn't always straightforward, and there are a few things that can go wrong—from personality clashes to poor company culture fit—that affect their performance, affecting your work.
  • Sometimes, the person may be qualified but is just not the best match for your work or communication style, industry, or personality.
  • No matter their experience and skills, VAs still need training and an adjustment period. Spend that time building a healthy professional relationship based on respect and clear communication.
  • Don't expect your virtual assistant to read your mind—communicate your needs and explain to them what you need them to achieve.
  • Virtual assistants may have some experience in tasks like digital marketing, sales, customer support, and social media management and may lend a hand, but they'll be more effective if they focus on just a couple of key areas of your business.
  • Establish some boundaries from the start and create a work environment that respects them.

Let us help

As a premium, fully managed, Virtual Assistant service we can take care of many of the things listed above and guide you through the entire process of finding and working with your ideal virtual assistant - saving you many potential issues and a lot of time along the way. We'd love to chat - get in touch with us today to see how we can assist you.

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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.

Psssst...want a free copy of my book The Hard Work Myth?

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