HOW TO CHOOSE THE RIGHT BOOKKEEPER

When I started my apparel company, I thought I had a pretty good handle on finances. After all, I had taken two accounting classes in college, and they were pretty much my favorite course. (Why did I go to college for apparel design again? Oh yeah, because I said that’s what I wanted to do in my 8th grade video… 🤔) Anyway, I understood the basics—debits, credits, reconciling—but what I didn’t realize at the time was how different real-world bookkeeping was from what I had learned in said college courses. 

I started out using QuickBooks for Mac, which I was just figuring out as I went. While I know what reconciling meant, I had no idea that there was a QuickBooks module for it. Managing cash flow? That was a mystery. I knew I needed a way to track how much cash we had and how much more we’d need to get through the year, so I built a spreadsheet in Excel to help. But I didn’t even know what to call it—I just knew I needed it. 

And then came the real struggles. 

I would put off updating my QuickBooks file for so long that catching up became my worst nightmare. I’d have to dedicate entire days to “reconciling” (not in the module) months of transactions, sometimes breaking down over being off by a single penny (sound familiar?). I had no idea how to fix the errors, and I didn’t understand QuickBooks well enough to make the process easier. 

That’s when I realized I needed help. Admitting there is a problem is the first step, right? 😉 

My Bookkeeper Hiring Journey: Lessons Learned the Hard Way 

At first, I didn’t even know what to look for. I ended up hiring a controller—which, let me tell you, was completely unnecessary for a small business like mine. We were making about $1M in revenue, but it was just me and my business partner. We didn’t need that level of financial oversight, nor did we have the funds to support it.  

Then, after talking to industry professionals and mentors, I finally understood I needed a bookkeeper. So, I hired one. She charged $30 an hour and took about four to five hours a month to do our books. She was a nice person and came recommended, but she couldn’t explain much of what she was doing. She worked in our home office on my MacBook, didn’t use cloud accounting, and while she got us to tax time, she didn’t provide any real insight into the business. 

And then I found Accounting Therapy (as a client.) They didn’t just get my books reconciled; they helped me optimize my processes that were very niche & specific to my industry. While they definitely charged more than $30 an hour, the work was done in almost a quarter of the time, and (most importantly) it was correct, and did I mention optimized? They could also have higher-level financial conversations with me about where the business was and what challenges we were facing. That’s when I first saw the difference between hiring a single contractor and working with a firm, plus I learned some questions to ask should I ever have to hire another bookkeeper.  

So, What Should You Look for in a Bookkeeper? 

So, fast forward to today: I work for Accounting Therapy and let’s just say my bookkeeping knowledge has grown 100-fold since the days of being an apparel small business owner. Lucky for you, dear reader, having had both experiences, I now feel very well equipped to give you some tips on what to look for in a bookkeeper! So, let’s dig in…  

If you’re a small business owner hiring a bookkeeper for the first time, here’s what I wish I had known before I started looking: 

1. How do they handle questions? 

• • • If they don’t know where to categorize a transaction, do they ask you? 
    • Do they proactively reach out if a new process appears in your books, or do they just assume and move on? Or worse yet, leave it to rot in an “ask my accountant” account. 
    • If something doesn’t reconcile, how is it handled? 
    • If they see inconsistencies in how something has been recorded over time, do they address it? 

A good bookkeeper asks questions and doesn’t just guess their way through your financials. 

2. Do they understand your industry? 

• • • Are they familiar with industry-specific workarounds, integrations, or additional apps that could help your business? If they are not, does their team have the capacity to learn? 
      • E.g. If you are an ecommerce company, do they work with Shopify/Square/Stripe? What are their options for you on how to record your sales? 
      • E.g. If you are a contractor or construction business, do they know about job costing? Can they help you implement time tracking by job with geofencing? 
    • Do they know the relevant tax regulations and compliance needs for your industry? 

Bookkeepers don’t have to be industry specialists, but if they don’t understand how your business operates, they might be missing opportunities to make your bookkeeping more efficient. 

3. Can they grow with you? What other services do they offer? 

• • • Do they offer additional services beyond basic bookkeeping, such as accounts receivable (AR) support or accounts payable (AP) management? What about payroll setup and processing? Sales tax? 1099s?  
    • Can they assist with cash flow forecasting and help you manage your cash flow as you scale? 
    • Do they have experience working with businesses that are similar in size and complexity to yours? 

Your business won’t always look the way it does today, so make sure they have the ability to support you as you grow.  

4. What kind of team & backup support do they have? 

• • • If your bookkeeper goes on vacation or is unavailable, who fills in? 
    • Is there a structured workflow that ensures continuity, or will the fill-in person have to ask you a million questions to catch up? 
    • Do they document processes so that someone else on their team can easily step in if needed? 

A single point of failure can be a major risk, so having a bookkeeper with backup support and defined processes is key. 

5. What does their typical client workflow look like? 

• • • How do they schedule your bookkeeping service and when can you expect your monthly reports? Do they send monthly reports? 
    • Do they align their timing with your needs, such as sales tax filing deadlines? 
    • If you need to provide them with month-end documents, when do they expect it and will they remind you? 

Understanding their workflow helps set expectations and ensures they align with your business operations. 

6. What are their year-end processes and expectations? 

This is a big one that often gets overlooked or forgotten about. Before hiring a bookkeeper, ask: 

• • • Do they reconcile your books to your last tax return or expect your CPA to do that? 
    • Are they proactive about gathering year-end documents like loan statements to ensure your liabilities reconcile and your interest expenses are recorded correctly? 
    • Do they review your Accounts Receivable (AR) and Accounts Payable (AP) to determine if anything should be written off? 
    • Are they monitoring AR/AP throughout the year or only at year-end? 
    • Do they take the lead on initiating year-end conversations? Or are you responsible for asking about the above items? 

Some bookkeepers only maintain the books and leave year-end adjustments to the CPA. Others proactively prepare for tax time, ensuring your records are clean before tax season rolls around. Neither is right or wrong, albeit if you leave it for your CPA, it may come with a bigger price tag.  

Independent Bookkeeper vs. Bookkeeping Firm: Which is best? 

There are pros and cons to both options, but the key differences come down to: 

If you’re a very small business with minimal transactions, an independent bookkeeper might be a fine starting point. But if you want accurate books that have more than one set of eyes reviewing them, financial insights, and scalability, working with a firm is often the better investment. 

Final Thoughts: You don’t know what you don’t know. 

When I first started, I had no idea what I didn’t know. I didn’t know what to look for, what questions to ask, or what a "good" bookkeeper even looked like – honestly, I don’t even think I knew what a bookkeeper was. But I quickly learned that hiring cheap and inexperienced (or on the flips side, overqualified) ended up costing me more in the long run. 

Whether you hire an independent bookkeeper or a firm, make sure you’re choosing someone who understands your business, asks the right questions, and has the processes in place to keep your finances in check. Plus, always aim to work with a team or a person you vibe with, i.e. if you own a surf shop and you’re getting stuffy suit and tie feels, probably not the best fit. Don’t underestimate the power of a good relationship and similar communication style! 

Until next time, stay smart!