When I started my career as an assistant, I didn’t expect that experience to shape how I now manage WorkBetterNow’s finance department and serve as General Manager. Along the way, I’ve come to truly appreciate the difference a skilled virtual bookkeeping assistant can make. 

The right assistant doesn’t just handle numbers—they bring clarity, precision, and peace of mind. They free up your time to focus on the big picture while ensuring your finances are in expert hands. If you’re searching for someone to fill that role, here are the key skills that can make all the difference.

1. Meticulous Attention to Detail 

In bookkeeping, even the smallest mistake can have big consequences. The best assistants catch errors before they snowball. I’ve worked with people who saved thousands of dollars by spotting a single misreported invoice. That kind of precision is invaluable. 

What to look for: Ask candidates about a time they caught an error and how they resolved it. Their response will reveal their approach to details.  

2. Proficiency with Accounting Software  

Tools like QuickBooks, Recur360, Xero, and FreshBooks are the bread and butter of modern bookkeeping, and proficiency in these tools is non-negotiable. Beyond that, familiarity with tools like Gusto for payroll or Expensify for managing receipts can take your bookkeeping to the next level.  A tech-savvy assistant can save you hours of manual data entry and significantly reduce errors.  

What to look for: During the interview, ask them to walk you through how they’ve used software to solve a real-world problem or improve efficiency.   

3. Stellar Organizational Skills  

An organized assistant sets up systems that make tracking expenses, deadlines, and cash flow effortless. True organization creates a system where you can find everything you need without hunting for it. This skill not only saves time but also brings peace of mind.   

What to look for: Ask how they manage their own work or keep track of deadlines. Their answer should demonstrate a clear system or strategy.   

4.  Excellent Communication Skills  

Numbers don’t speak for themselves—you need someone who can explain them in a way that makes sense.  I’ve led assistants who’ve made complicated financial reports easy to understand and who communicate effectively with my accountant, vendors, and team. Clear, concise communication can save so much time and avoid unnecessary stress  

What to look for: Ask candidates to explain a complex financial concept in simple terms. You’ll quickly see if they can bridge the gap between data and decision-making.   

5. Confidentiality and Integrity  

Let’s face it: hiring someone to manage your or your company’s books requires a level of trust that’s not easy to come by. Your assistant will have access to sensitive financial information, and you need to know they’ll handle it responsibly.   

Before I hire anyone, I always check references thoroughly and look for signs of integrity in how they’ve handled sensitive data in the past. It’s one thing to manage numbers; it’s another to manage trust. 

What to look for: Check references and ask about how they handle sensitive information or situations that required discretion.  

6. Analytical and Problem-Solving Abilities 

Whether it’s identifying spending trends, flagging inefficiencies, or forecasting potential cash flow issues, a great assistant’s insights can guide smarter decisions.   

One of our finance assistants noticed that our subscription expenses were ballooning. They presented a detailed breakdown and helped negotiate lower rates with vendors. That kind of proactive problem-solving made a tangible difference to our bottom line.   

What to look for: During the interview, ask how they’ve identified and solved a financial issue in the past. Look for examples that show initiative and critical thinking.   

7. Adaptability and Growth Mindset  

The business world moves fast, and you need someone who can keep up.  One of our WBN bookkeeping assistants recently showcased these qualities by learning to incorporate ChatGPT into their workflow for creating financial summaries. With no prior experience using AI tools, they took the initiative to explore ChatGPT’s capabilities, identifying ways to streamline the preparation of clear, accurate overviews of financial data. 

What made this even more impressive was their ability to balance innovation with caution. They quickly adapted to leveraging this new tool while ensuring that sensitive data was never inputted, showcasing a commitment to both efficiency and security. This proactive approach not only saved time but also demonstrated their willingness to grow and embrace new technology to deliver even greater value. 

What to look for: Ask candidates about a skill they’ve recently learned and how it’s improved their work. This reveals their willingness to adapt responsibly. 

The Real Value of a Great Assistant   

When businesses hire the right bookkeeping professional, the transformation is undeniable. Many of our clients who have hired WorkBetterNow Certified Professionals™ for bookkeeping have shared how it’s not just about keeping the numbers straight—it’s about gaining clarity, control, and the confidence to make smarter decisions. 

From uncovering cost-saving opportunities to setting up systems that streamline financial management, our clients have seen firsthand how a skilled professional can turn finances from a source of stress into a foundation for growth. 

WorkBetterNow (WBN) provides outstanding remote talent to small and midsize businesses. WBN’s highly skilled and pre-vetted Latin American professionals are hand-matched for each client’s unique needs. Hundreds of growing businesses turn to WBN to unleash their potential through our exceptional talent, ease of hiring, and ongoing support. Request a consult today!