Hiring a Bookkeeper: What 17 Years of Hiring Taught Me.

After 17 years of hiring bookkeepers, I've learned that every part of the hiring process tells you something. A resume, an interview, and a reference each provide valuable information. The challenge isn't gathering more information; it's understanding what each piece is actually telling you and how much weight to give it.

Early in my career, I hired candidates who interviewed well, had impressive experience, and said all the right things. More than once, I walked away feeling confident that I'd found the right person, only to realize a few weeks later that something wasn't working.

Each experience taught me something, and over time they changed the way I approached hiring. These are the lessons I find myself coming back to every time I evaluate a bookkeeping candidate.

Lesson #1 Strong Candidates Don't Always Give the Strongest Interviews

This was one of the hardest lessons for me to learn. 

When you're interviewing someone, it's natural to gravitate toward the candidate who communicates confidently. They have quick answers. They speak comfortably about reconciliations, month-end close, and client communication. They leave you thinking, "This person knows their stuff." And sometimes, they do. 

But I've also met excellent bookkeepers who didn't interview particularly well. 

They took a little longer to answer, they asked for clarification, they weren't trying to impress me with polished answers. They were approaching the conversation the same way they would approach a client's books: carefully and methodically. 

Looking back, those candidates often became some of my strongest hires.

That's why I've learned to pay attention to how someone answers, not just how confidently they answer. If a candidate slows down to think, asks thoughtful follow-up questions, or wants to understand the situation before giving an answer, I see that as a positive. Those are the same habits that help someone catch errors, investigate discrepancies, and make good decisions once they're on the job.

Lesson 2: Experience Is Only Valuable If It Can Be Applied

When I first started hiring, I paid a lot of attention to where someone had worked and how many years of experience they had.

Today, I care much more about what they can actually do with that experience.

Someone may have spent ten years in bookkeeping, but if their role involved repeating the same routine every month, they may have had very little exposure to troubleshooting, investigating discrepancies, or working through unfamiliar situations.

On the other hand, I've met candidates with fewer years of experience who developed excellent judgment because they were consistently solving problems and asking good questions.

Years in the profession tell a part of the story, but they're much more meaningful when you understand what that experience actually looked like day to day. 

Lesson 3: References Rarely Change My Mind

I've rarely had a reference tell me something completely unexpected. Most references are positive, and understandably so.

What they can do is reinforce what you've already observed during your hiring process.

I still check references, and I think they're an important part of the process. What I've learned over the years, though, is that they rarely change my hiring decision. Instead, they tend to confirm what I've already observed. By the time I reach that step, I want to know the candidate can do the work, so I'm using that conversation to learn about everything a resume and interview can't fully capture. How do they communicate? How do they handle feedback? Are they someone their previous employer would genuinely hire again?

Those answers add valuable context, but they are not the foundation of my hiring decisions. 

Lesson 4: The Details Matter More Than You Think

One pattern I've noticed over the years is that candidates often reveal as much in the small details as they do in the big interview questions.

It's easy to focus on technical knowledge, but I also pay attention to how carefully someone follows instructions, whether they read the entire prompt before answering, and if they take a moment to review their work before moving on.

Those habits may seem minor during the hiring process, but they're often the same habits that show up once someone is responsible for client work.

Bookkeeping is a profession where consistency matters. The people who routinely catch small issues before they become bigger problems are usually the ones who have developed a habit of slowing down, paying attention, and checking their work.

I've learned not to overlook those small signals because they're often a preview of how someone will approach the role once they're hired.

Lesson 5: A Good Hiring Process Should Keep Evolving

The biggest lesson I've learned over the last 17 years is that a hiring process should never become so familiar that you stop questioning whether it's still working.

The way I evaluate candidates today looks very different from the way I approached hiring early in my career. Some of the questions I once relied on no longer tell me very much, while other parts of the process have become more important because experience showed me what they reveal about a candidate. I've changed what I listen for during interviews, how I evaluate previous experience, and what I need to see before I feel comfortable extending an offer.

Those changes came from looking more closely at what each hiring process had shown me before the person joined the team. When someone became a strong, dependable hire, I wanted to understand which qualities had been visible early on and how I could recognize them again. When a hire struggled, I looked back at where I may have made an assumption or failed to evaluate something thoroughly enough. 

Experience has given me greater confidence in my hiring decisions, but it has also taught me to keep refining how I make them.

Want to apply these lessons to your own hiring process?

I've put together a Bookkeeper Hiring Checklist: 12 Steps to Hire with Confidence, a practical framework to help you evaluate candidates, reduce hiring risk, and make more confident, evidence-based hiring decisions before extending an offer.

Looking Back

The bookkeeping profession has changed considerably over the last 17 years. Bookkeepers are working with more technology, communicating more directly with clients, exercising stronger judgment, and taking greater ownership of the financial information they manage. A hiring process that worked well years ago may no longer reflect what firms need from their bookkeepers today.

That's why I continue to revisit my own process. Every candidate, every successful hire, and every hiring decision that didn't work out has given me more information about what to look for and where the process can improve.

Hiring will probably never become completely predictable, but it can become more informed. The more clearly we understand what we're evaluating and why it matters, the better chance we have of recognizing the candidates who will truly succeed in the role.

If you're looking to bring that same confidence to your own hiring process, BookkeepingIQ provides live-proctored bookkeeping assessments that allow candidates to demonstrate their skills before an offer is made. Instead of relying solely on resumes and interviews, you'll have objective insight into how a candidate performs in a real bookkeeping environment.

Explore our bookkeeping assessments and employer resources to learn how BookkeepingIQ can help you hire with greater confidence.