How to Work With a Bookkeeper: Supporting Your Business and Streamlining Your Financial Systems
- Kayli Robles
- Dec 9, 2025
- 5 min read
Wondering how to work with a bookkeeper and what they can do to support your growing business?
Whether you’re not a numbers person and want the support of someone who is, or you are but your growing business needs your full attention, a bookkeeper can be an invaluable part of your team.
Your bookkeeper manages the financial details of your daily operations. In doing so, they help you set a strong foundation for your business to build upon by adding clarity to the numbers and providing the data you need to make business decisions with confidence.
Bookkeeping services can vary, so if you’re feeling uncertain about exactly how to work with a bookkeeper to reach your business goals, you’re in good company. Let’s demystify the process with an overview of how best to work with a bookkeeper, and what they can do to support your business.
How can a bookkeeper support my small business?
One of the greatest benefits to working with a bookkeeper is that they’ll take the financial record keeping duties off of your plate.
Bookkeepers help streamline your business’s financial systems by applying their expertise, efficient workflow, and dedicated accounting software to meet your needs.
Beyond standard data entry, bookkeepers prepare reconciliations that ensure your financial records are accurate, and internal financial reports that help you understand the financial current of your business. Bookkeepers often provide payroll support as well, which can be a great help in ensuring your employees are paid on time, with the correct withholdings.
Working with a bookkeeper can also support your financial decision-making. With their detailed knowledge of your business’s financial world, they can play an important role in helping you manage your business’s cash flow or flag anything that seems off for a second look. Bookkeepers can also generate specific internal financial reports that help you assess key metrics for financial health, spot trends, and forecast your financial future.
Not everyone works with an accountant, but if you do, you can rely on your bookkeeper to be their main point of contact and answer any financial questions that they have.
For more on this, you may enjoy this post: Pro Tips: Making the Most of Your Partnership With Your Bookkeeper
Wondering what the difference is between a bookkeeper and an accountant? Here’s your next read: What’s the Difference Between a Bookkeeper and an Accountant (and Which Do I Need?)
What to expect when working with a new bookkeeper
All bookkeepers will have their own onboarding process, and might have different requirements and styles of communication depending on their area of expertise and the services they provide.
A common onboarding process might look like this:
You’ll have an initial consultation, making sure that your bookkeeper is the right fit and can provide the services you’re looking for. The bookkeeper will likely go over their process, how to provide documents, what software they use, and how communication will work. Don’t forget to bring your questions!
If you had a bookkeeper before, or if you’ve been doing your own books, your new bookkeeper may ask for your historic bookkeeping records. Otherwise, they can set you up in their system from scratch.
It’s likely your new bookkeeper will have many questions (and follow-up questions). This is to get up to speed on your business’s financial world, and to ensure that your financial records are accurate. As you work more together, the process will become more streamlined.
Your new bookkeeper will set you up in their system and give you access to their accounting software so that you can see your financial data in real time.
Once onboarding is complete, the work can begin!
What your bookkeeper needs from you
You and your bookkeeper will be in frequent contact to make sure that your financial records are accurate.
What kind of documents will your bookkeeper need? You might provide any or all of the following:
Bank and credit card statements
Invoices and receipts
Sales data (including your issued invoices, or data downloaded from your sales platform)
Employee salary and wage information for payroll
Loan agreements and schedules of repayment
Your notes on cash transactions that might be unclear (for example, a personal draw, or a personal expense paid through a business account, might not be obvious from your bank statements)
Your notes on any business-related expenses that were paid from a personal account, ensuring they’re captured in the books
Do expect questions from your bookkeeper as you work together! They may need clarification on some transactions, especially cash transactions without a description, or when it’s not clear how best to categorize an expense. Any unusual transactions may also warrant a check-in, just to be sure.
Along those lines, if you make any business decisions or changes, it’s great to keep your bookkeeper in the loop. That might look like hiring a new employee, changing service providers, or taking out a new loan. Your bookkeeper will appreciate the heads-up! They can get ahead of the documentation that they’ll need related to the change, and they’ll be on the lookout for it in your transactions.
For tips on putting together documents for your bookkeeper, you may enjoy: How to Put Your Monthly Package Together for Your Bookkeeper (and What to Include)
Five tips for working with your bookkeeper effectively
Being in constant communication is not for everyone — running a business is demanding! While some clients do prefer to simply drop off their monthly package and carry on, there are some bookkeeping best practices that can help streamline the process.
Ask questions! Don’t hesitate to ask about deadlines, preferred methods of communication, or even the details of the reports that you’ll receive. Need some ideas? We’ve compiled six questions to ask your bookkeeper to build financial confidence and clarity.
Similarly, don’t be afraid to get into the details. Don’t understand something in your financial reports? Let your bookkeeper do what they do best, and talk numbers. Your bookkeeper wants to make sure that the numbers are meaningful to you.
Get organized. You can ask your bookkeeper for any tips on how to organize your monthly package. A complete, organized package of documents will help your bookkeeper produce cleaner books, with less back-and-forth time.
Speaking of back-and-forth time, try to respond to your bookkeeper’s questions as soon as you can. This helps keep your records as complete as possible in real time while avoiding bottlenecks, such as a vital piece of missing information.
Find the sweet spot between your communication style and theirs. What does your ideal relationship with your bookkeeper look like? Do you prefer minimal contact, or do you like weekly check-ins? In-the-moment emails, or a biweekly update?
Ready to find clarity and confidence in the numbers?
Robles Bookkeeping takes an efficient and reliable approach, tailored to your specific needs.
If you’re ready to simplify your financial workflow, click here to schedule a free evaluation of your books! I would be happy to discuss how I can help save you time, freeing you to spend that time where it matters most: growing your business.



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