It’s late. You’re sitting at your desk and the numbers just aren’t adding up. Your desk is covered with receipts, tax season is looming, and you’re up to your eyeballs in paperwork that should have been completed months ago. 

You’re frustrated, overwhelmed, and starting to wonder if you’ll ever get back to the side of your business you actually love. You know it’s time to make a change—it’s time to fire yourself as the DIY CFO of your company and hire a real bookkeeper! 

But how do you find the right one?

It’s important to know what to look for in a bookkeeper when you start your search. Let’s get into the bookkeeping basics so you can invest in a bookkeeper that is perfect for you. 

It’s Time to Hire a Bookkeeper If…

Look, we get it—you’re the CEO, the marketer, the HR department, and sometimes even the janitor. But if you’re turning into your own full-time bookkeeper, something’s gotta give. 

Here’s the deal: if you’re drowning in spreadsheets and losing track of what actually makes your business tick, it’s time to call in the pros. (You wouldn’t fix your own car without a mechanic, right? Same rule applies to your books!) 

It’s time to hire a bookkeeper if:

  • Your Books Are a Mess. Receipts are piling up, and your accounts haven’t been reconciled in months. If managing finances feels overwhelming, it’s time for expert help.

  • You’re Missing Tax Deadlines. If tax season is stressful and you’re constantly scrambling to meet deadlines, a bookkeeper can keep your finances organized and compliant year-round.

  • Cash Flow Is Unpredictable. If you’re unsure where your money is going or struggling to keep track of payments and expenses, a bookkeeper can bring clarity and consistency to your
    cash flow.

  • Growth Is on the Horizon. As your business expands, so do your financial responsibilities. A bookkeeper helps your financial systems grow with you so you can focus on scaling your operations.

  • You’re Not an Expert in Finances. Let’s face it—unless you’re a trained accountant, bookkeeping can be complex. If you’re unsure about managing your books, it’s time to delegate to someone who knows the ropes.

What Exactly Does a Bookkeeper Do?

A bookkeeper keeps your financial house in order. While you’re out there hustling, they’re behind the scenes tracking expenses, keeping an eagle eye on your income, and whipping up reports faster than you can say ‘tax season.’ 

Basically, they save you from living in spreadsheet purgatory so you can get back to doing what you actually love—growing your business.

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Tasks That a Small Business Bookkeeper Manages

A bookkeeper is the financial backbone of your business. From handling your day-to-day money moves to prepping for the dreaded end-of-year reporting, they’ve got it covered. Here’s a sneak peek at what they do behind the scenes:

Track financial transactions

Your bookkeeper is a financial detective. They’re on top of every sale, expense, and payment so that your books are balanced and your financial records are clean. 

Manage payroll

A bookkeeper may handle everything from collecting work hours to calculating paychecks—including deductions and benefits—so you don’t have to worry about a thing.

Maintain financial records

They keep your records so fresh, so clean, and most importantly—accurate. Whether it’s making sure everything’s audit-proof or keeping you compliant with all those pesky tax regulations, they’ve got it under control. 

Handle financial obligations

Bills, loans, taxes—your bookkeeper makes sure all your financial obligations are handled on time. They keep track of what’s due to help you avoid late fees and keep your business’s finances in good standing. 

Prepare financial reports

At the end of the month, quarter, or year, your bookkeeper puts together detailed financial reports. These reports are like a check-up at the doctor—they give you a clear view of your business’s financial health.

Improve processes 

A great bookkeeper is always looking for ways to streamline processes and enhance accuracy so that your financial records are not just up-to-date but also optimized for efficiency. 

Give financial advice.

Most good bookkeepers will also walk through your financials and advise you on financial decisions for your business and act as a thought-partner.

12 Qualities to Look for in a Bookkeeper

With a saturated bookkeeping market, it can be hard to sift through resumes and automated websites. Here is a checklist of qualities to scan for on your bookkeeping search:

1. Trustworthy

Your bookkeeper will have access to sensitive financial information, so trust is non-negotiable. Look for someone with a solid reputation and positive testimonials that vouch for their integrity and reliability.

2. Knowledgeable

A great bookkeeper stays on top of the latest financial regulations and industry trends. They should be well-versed in accounting principles, tax laws, and the specific needs of your business.

3. Organized

With so many moving parts in bookkeeping your bookkeeper should have a system in place for managing financial records, deadlines, and daily transactions without missing a beat.

4. Detail-oriented

The details matter in bookkeeping. A detail-oriented bookkeeper will catch the small errors that can lead to big problems—there has to be accuracy in every aspect of your financial records.

5. Client-centric

Your bookkeeper should prioritize your business’s unique needs. They should take the time to understand your goals and tailor their services to help you achieve them with personalized support.

6. Proactive vs. reactive 

A top-notch bookkeeper doesn’t just react to issues—they anticipate them. Look for someone who proactively identifies potential financial problems and offers solutions before they become crises.

7. Tech-savvy

Your bookkeeper needs to be tech-savvy. They should be skilled in using accounting software and managing data entry efficiently. Check out their tech deck and see if they are keeping up with industry trends. 

8. Communication

Clear communication is essential for a smooth working relationship. Your bookkeeper should be able to explain financial concepts in a way that makes sense to you and keeps you informed about your financial health.

9. Problem-solving

When financial challenges arise, you need a bookkeeper who can think on their feet. Problem-solving skills are important for dealing with unexpected issues and finding practical solutions quickly.

10. Understanding

Every business is unique, and your bookkeeper should understand the nuances of your industry. Hire someone with experience in your field who can provide insights tailored to your specific needs.

11. Ethical integrity

You need a bookkeeper who adheres to the highest ethical standards. They should be transparent, honest, and committed to maintaining the confidentiality of your financial information.

12. Clarity

A great bookkeeper won’t shy away from asking questions to clarify details. They know that making assumptions can lead to mistakes, so they prioritize accuracy by seeking out the right information.

How to Identify Qualities in a Bookkeeping Candidate

How do you identify these qualities in a bookkeeper? It’s all about asking the right questions. Here are some of my favorite interview questions to get you started:

  • Which accounting software are you most comfortable with, and why?
  • Can you walk me through your experience in different industries?
  • How do you catch and correct errors in the ledger?Have you had to switch to new accounting software before? How did you handle it?
  • How do you keep up with the latest bookkeeping practices?
  • What systems do you use to stay organized?
  • Can you explain the three-way match process?
  • How would you address a minor discrepancy during a bank reconciliation?
  • How do you communicate financial details to clients?

small business bookkeeping

What to Look for in a Bookkeeper—Frequently Asked Question

Is a bookkeeper cheaper than an accountant?

Yes, bookkeepers are generally less expensive than accountants because they handle daily financial tasks like recording transactions and managing payroll, while accountants focus on higher-level financial analysis and tax preparation.

Is it worth getting a bookkeeper?

Yes, hiring a bookkeeper is worth it because they save you time and ensure your financial records are accurate. This allows you to focus on growing your business without getting bogged down by bookkeeping tasks.

What questions should you ask your bookkeeper?

Key questions to ask include: “Which accounting software do you prefer?”, “How do you handle errors in financial records?”, and “How do you keep up with changes in bookkeeping practices?” These questions help assess their expertise and fit for your business.

How much should I spend on a bookkeeper?

Expect to spend between 1-5% of your monthly revenue on bookkeeping services. The exact amount depends on the complexity of your financial needs and the level of service you require.

Do I need both a bookkeeper and an accountant?

Yes, having both a bookkeeper and an accountant is ideal. A bookkeeper handles daily financial tasks, while an accountant provides higher-level financial analysis and tax preparation, ensuring comprehensive financial management for your business.

Find Your Perfect Bookkeeping Match with Bookkeeping Match Up!

Finding the perfect bookkeeper doesn’t have to be a guessing game. 

With Bookkeeping Match Up, we take the hassle out of the process by connecting you with pre-vetted bookkeepers tailored to your business’s unique needs. Book a free call today, and let’s find your perfect bookkeeping match—because your business deserves the best.

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