When Is the Right Time to Hire a Bookkeeper?

Every business has needs as unique as its owner. Some businesses hire a bookkeeper from day one, while others prefer to manage their own books for many years. 

The decision to start working with a bookkeeper often depends on:

• Your level of comfort with bookkeeping 

• The amount of time you have available to manage your books

• The size of your business and how quickly it’s growing

• The complexity of your transactions and reporting requirements

• Your needs when it comes to reviewing and using financial data

If you’ve been wondering whether now is the right time, this quick guide may offer some helpful insight.

Here are five clear signs that it’s time to hire a bookkeeper:

1. When doing your own bookkeeping feels overwhelming

We’ve all been there — just the thought of tackling this month’s bookkeeping sends you looking for anything else you can do to feel productive.

Running a business is stressful enough. When doing your own books starts adding to that stress, it’s probably worth considering adding a bookkeeper to your team.

Even more so if you’re frequently procrastinating on your bookkeeping tasks — especially if it’s because you need to focus on running your business. Operating your business is the highest-value use of your time, but it’s still essential to keep your books accurate and up to date throughout the year. That’s where a bookkeeper can be a great asset.

2. When you’re struggling to answer your accountant’s questions

If you only work with your accountant a few times per year (or less), you know that they may have questions about the details of your books that can relate to things that happened a long time ago. 

You might find it costs too much of your time to dig into the books to find the information that they’re looking for. Or, you may find it a challenge to keep up with the debits and credits they’re referring to.

Either way, working with a bookkeeper can help alleviate some of the stress:

• Cleaner, more accurate books can lead to fewer questions and more efficient tax preparation.

• A bookkeeper can quickly drill down into the data and pull the reports your accountant needs, along with supporting backup.

• Your bookkeeper also speaks in debits and credits, so communication is smoother (and your workload is lighter). 

3. When you’re planning to expand

No matter what your expansion looks like, you can bet that it will increase the volume of transactions and the amount of financial data that you’ll want to track. For example:

• More construction projects require additional job-costing

• A new business line requires separate cost and profitability tracking

• A new location comes with new agreements and expenses to track and manage

• Hiring employees increases payroll transactions and reporting requirements 

If you’re hiring employees for the first time, you may be new to payroll processes and compliance. Professional payroll services or payroll setup support, which some bookkeepers provide, can be especially helpful in supporting you through the process. 

The right bookkeeper can help you manage the higher volume of transactions and track the financial data that matters most for business decision-making and cash flow monitoring. 

4. When your cash flows are feeling a bit foggy

Is cash flow management feeling more reactive than proactive? If you’re dealing with missed bills, long-outstanding customer invoices, or scrambling to cover surprise costs, it may be because:

• Bookkeeping isn’t completed consistently, making financial data less relevant.

• You haven’t had time to digest financial results and what they mean for your cash flow.

• Errors such as misclassifications or duplicate entries are muddying the flow of cash.

These are just a few examples that suggest it might be time to bring on some additional support. A bookkeeper can help you keep your books accurate and up to date so that you can monitor your cash flows and plan ahead for upcoming costs.

Cash flow support is typically outside the essential bookkeeping process, but even requesting additional reports can be helpful. If you’re considering hiring a bookkeeper, you can ask what kind of support they’re able to provide. For more tips on choosing the right bookkeeper, you may find this resource useful: 10 Questions to Ask Before Hiring a Bookkeeper

For a broader overview of bookkeeper roles and responsibilities, you might also enjoy: What Is a Bookkeeper? A Simple Guide for Small Business Owners

5. When small mistakes could have expensive consequences

As your business grows, so does the room for error — and those errors can start costing much more than just your time. Errors such as misclassifications, duplicate entries, or missing transactions can cause issues in your tax filings, payroll reporting, or financial reporting.

The cost might include higher accounting fees needed to fix errors at year-end, the cost of potential future audits, or even penalties and interest resulting from filing errors. 

Working with a bookkeeper can reduce this risk considerably by ensuring books are clear and accurate throughout the year, and any errors can be addressed as they arise, rather than only at tax time.  

If the time is now, we’re here to help

To run your business effectively, you need accurate numbers and a reliable partner to discuss them with you in a clear, practical way. 

We offer a full suite of bookkeeping services tailored specifically to your business. If you’d like to explore next steps, it’s quick and easy to schedule a free evaluation of your books so we can determine how best to support you. We look forward to connecting.