If you’re considering hiring a Virtual Bookkeeping Assistant, you probably have many questions.

Finding the right talent for your business is difficult, and hiring virtually might seem even more daunting. However, the good news is that hiring remotely is easier since you can pick from a broader talent pool and are not restricted by location.

Still, while the role of a virtual bookkeeper is no different from an in-house bookkeeper, there are slight differences in how they operate. Therefore, to have a smooth and seamless professional relationship, you’ll want to ensure you are hiring the right person for the job.

To make things easier, we’ve put together a list of questions that will help you narrow down your list of candidates until you find your perfect fit.


Who is a Virtual Bookkeeping Assistant?

A Virtual Bookkeeping Assistant is a qualified accounting professional who operates remotely and helps your company manage its finances.

They save entrepreneurs significant time and money by taking care of menial and tedious routine tasks that are still important and need to be done.

The only significant difference between an in-house accountant and a Virtual Bookkeeping Assistant is that a virtual bookkeeper does not work from your office but operates from their own house or a co-working space. However, thanks to modern technology, they can still be part of important company meetings through video conferencing.

Some of the tasks you can outsource to your Virtual Bookkeeping Assistant are -

  • Making sure your bills are paid on time
  • Preparing Balance Sheets Or P&L accounts
  • Reconciling bank statements
  • Preparing invoices and general ledgers
  • Sales Tax Reporting
  • Mailing invoices to customers
  • Managing financial data, and
  • Entering payables and receivables

For a more detailed list of tasks, you can delegate to a Virtual Bookkeeping Assistant, read our blog: 14 Bookkeeping Tasks A Virtual Assistant Can Do For Entrepreneurs.

Source: Unsplash

10 Questions to ask before you hire a Virtual Bookkeeping Assistant

What are your working hours, and what is your availability?

Virtual Assistants work from all over the world. For example, your office could be based in Los Angeles, and your Virtual Assistant could be based in India. Therefore, having clear communication on work hour expectations is very important.

The good news is that Virtual Assistants work flexible hours and can be very accommodating with their schedules. Even more so, if you hire from a virtual assistance agency like Wishup, you can find a Virtual Assistant who works your preferred schedule. So timing is not an issue.

You will also need to discuss the hours you expect them to work for your business. Since they are not permanent employees, you can decide their workdays based on your budget and workload size. For example, your Virtual Assistant could work for your business Monday to Friday like a regular employee, but if the workload is light, you could also request them to work for only two days a week.

Every company is different, and it’s vital to lay out the crucial details beforehand so there’s no room for miscommunication later on.

How will we communicate?

When you work with an in-house bookkeeper, you don’t even think about communication since they work in the office.

But, with a Virtual Bookkeeping Assistant, deciding the means of communication is crucial for your working relationship. You will need to find a Virtual Assistant who can accommodate and adjust to your means of communication. For example, if you communicate through a platform like WhatsApp or Slack, your Virtual Assistant must be familiar with these tools. Or, if you prefer to communicate via video chat, your Virtual Assistant will need to install the right software to make communication easier.

You will also need to discuss how often you communicate with your Virtual Bookkeeping Assistant. While Virtual Assistants are pretty independent in their workstyle, you will still need to communicate regularly to give them instructions or get work updates. We recommend a 15-20 minute call every day or every alternate day to ensure things are on track.

At Wishup, our virtual bookkeepers file an end-of-day report daily that lets you know how they spend their time at work. This way, even if you don’t communicate daily, you’ll still be aware of what work is completed by your assistant.

Tell me about your past work experiences and what is your area of interest/expertise.

Much like hiring an in-house bookkeeper, it is preferable to hire a virtual bookkeeper with experience working in similar environments to your business. For example, if you work in real estate, a Virtual Assistant who’s worked as an accountant in a realtor’s office would adapt to your business much faster than someone who has worked in e-commerce or education.

Additionally, you want someone on your team who is genuinely interested in the type of work you do. Only then will it be a mutually beneficial working relationship, where both parties can help each other grow.

Pay attention to the way they speak when they answer these questions. If they sound enthusiastic and interested in the opportunity, it’s a good sign. Another good sign is if your potential Virtual Assistant asks you questions and is eager to learn more about the position.

Tell me a time when things didn’t go according to plan and how you handled the situation.

Everything isn’t always going to be smooth sailing in a business. There are bound to be times when things go wrong, deadlines are missed, or unexpected mishaps happen. Even if you hire the most qualified person, things might be beyond their control.

However, what is in your hands is hiring someone who can keep their head on your shoulders when things go awry.

Ask them, for example, how they managed to follow up with a client who wasn’t making a payment on time or how they kept things running when their computers crashed. This is especially important, as their work majorly depends on being available on the computer.

At Wishup, we have a challenging aptitude test and select only the top 1% of applicants, who are then trained on various aspects of the job and how to handle any difficulties that may arise. We also ensure that our Virtual Assistants are equipped with proper tech and have backup arranged in case of an emergency.

Source: Unsplash

How are you going to be a proactive member of the team?

Though they work remotely, a virtual bookkeeper will still need to maintain close relationships with certain members of your team, as accounting needs to work with different departments in the company. Therefore, you will need a team player who will contribute to your business’s success.

Additionally, you don’t want a person you will have to spoonfeed. A good virtual bookkeeper can proactively understand what needs to be done and take charge of their work.

A proactive virtual bookkeeper will identify things that can be improved and pinpoint inefficient processes that can be streamlined. This will help your company save time in various ways - such as cutting down meetings, improving communications through various software, finding more affordable vendors, and more.

At Wishup, we hire college graduates with previous office experience. Though they work remotely, they have worked in various office settings before and can use their vast experience to help streamline operations and make them more efficient.

What are your salary expectations?

Money can be a tricky subject to bring up, especially in a virtual interview.

Just remember the budget you have set aside for hiring a virtual bookkeeper and start from there. Doing your own research is a good starting point before you begin interviewing candidates.

A Virtual Assistant with more experience and better qualifications will charge more. This is when you will need to decide if you can compromise on qualifications to cut costs.

The important thing to remember is that you are already cutting costs significantly by hiring a Virtual Bookkeeping Assistant. By choosing a Virtual Assistant, you eliminate expenses like paid leaves, insurance, and additional costs of having an in-house assistant. To put things in perspective, a regular bookkeeper might cost you close to $45,000 a year, whereas a Wishup virtual bookkeeper will cost you only $20,000.

Thus, even if you choose to work with a qualified virtual bookkeeper, you will still be saving money compared to if you were hiring an in-office bookkeeper.

What would you do if given an assignment you didn’t understand?

This is important to assess whether you are hiring a virtual employee or an in-house bookkeeper. However, communication with your virtual bookkeeper is not as often as with someone who works in the office. Therefore, you will need a person who is not afraid of admitting their shortcomings and is willing to face challenges and learn on the job.

Every business is different, and there is always something new to be learned. At Wishup, we understand that and try to equip our virtual bookkeepers with all the necessary knowledge they’ll require for the job. Our in-house training program covers over 70 crucial skills and tools that will come in handy to them on the job.

Note their response to this question. A good virtual bookkeeper may have never been given an assignment they didn’t understand. But a great virtual bookkeeper is one who faced a new challenge, wasn’t afraid to admit their shortcomings, and was ready to learn something new.

Source: Unsplash

What is your turnaround/delivery period?

It’s important that everyone is on the same page once you hire a virtual bookkeeper. And deadlines are one of the most crucial aspects to consider before hiring someone. You want someone who works quickly and can meet short deadlines without making mistakes. Ofcourse, you must have reasonable expectations of your virtual bookkeeper.

Additionally, regular deadlines and emergency deadlines are not the same. Sometimes, an urgent invoice needs to be sent out to a client. Or, an urgent financial report might need to be made. Not all of these might be during their work hours. You want someone ready to occasionally go the extra mile and be an asset in times of need. That’s what makes a great employee.

At Wishup, we assign a success manager to every client who oversees the project and the work of the virtual bookkeeper. We value and trust your business and will ensure no missed deadlines.

How can I trust you with my private data?

Working with a virtual bookkeeper essentially means trusting them with really important and sensitive information, such as your passwords and bank details. Naturally, therefore, you’re bound to be worried about the security of your data, and rightfully so.

With freelancers, there is a risk of misusing your information unless proper contracts are signed, and a third party is involved. This is why people prefer to work with Virtual Assistant service providers rather than hiring freelancers.

At Wishup, we take your privacy seriously. We have set rules and guidelines set in place and a non-disclosure agreement that all our Virtual Assistants sign. Therefore, you can rest assured that your data and information are in safe hands.

For more information, read our blog: How Wishup Ensures the Security of their Clients' Data.

Do you have any terms or conditions of business?

Lastly, find out their usual terms and conditions, if any. This information might already be available on their resumes or the website of the virtual assistance agency they work for. Still, it is best to clear this out with either the bookkeeper or the client success manager before hiring.  This covers regular aspects like trial periods, minimum and maximum delivery time frames, contract length, payment processors, and any other details you might want to discuss.

Your time is valuable, something we at Wishup understand too well. This is why we schedule a short, free consultation with our clients. We discuss your expectations and needs and pair you with the perfect virtual bookkeeper. The whole process takes less than 24 hours, and you will have a bookkeeping assistant ready to start the job.


What are you waiting for? Grow your business with a Virtual Bookkeeping Assistant now!

Hiring a quality bookkeeper is challenging, but we can make it simple. If you are interested in growing your business with a remote team of talented bookkeepers, join our team of over 500 happy clients and schedule your consultation today! You could also drop us an email at [email protected], and we will get back to you at the earliest.

Bookkeeping assistant virtual bookkeeping assistant virtual bookkeeping services
Swapna Ravichandran

Swapna Ravichandran

When I'm not writing you can find me curled up with a book & a cup of hot coffee, exploring the city's newest restaurants for my food blog, and spending any other free time I have on the beach.

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