What should I expect during the first month with a new bookkeeper?
The first month with a new bookkeeper is not going to feel like a finished product. It is almost entirely about setup, information gathering, and building the foundation that makes every month after it run smoothly. If you go in expecting polished financial reports on day one, you will be disappointed. If you go in expecting a lot of questions and a bit of a learning curve on both sides, you will be in good shape.
The process usually starts with access. Your bookkeeper will need login credentials or invitations for your accounting software, bank accounts, credit card accounts, payroll system, and any other platforms where money moves. If you are using QuickBooks Online, this means adding them as an accountant user. The faster you provide access, the faster everything else moves.
After that comes the review phase. A good bookkeeper will look at the current state of your books before changing anything. They want to understand your chart of accounts, how transactions have been categorized, whether reconciliations are current, and where there might be gaps or errors. This is where they figure out how much cleanup is needed before they can start maintaining things going forward. Sometimes the books are in decent shape and just need minor adjustments. Other times there are months of uncategorized transactions or bank accounts that were never reconciled.
Expect a lot of questions during this phase. Your bookkeeper does not know your business yet. They will ask about recurring transactions, vendor relationships, how you handle payments, whether certain charges are personal or business, and what categories make sense for your specific situation. This is a good sign. A bookkeeper who doesn’t ask questions during the first month is probably guessing, and guessing leads to bad data.
By the end of the first month, you should have a clear picture of where things stand. Your bookkeeper should be able to tell you what shape the books are in, what needs to be cleaned up, and what the ongoing process will look like. You might get your first set of reconciled financials, or you might get a plan for catching up if the books were behind. Either way, you should understand the timeline and what comes next.
Communication expectations matter too. Talk about how often you will check in, whether that is weekly emails or a monthly call. Ask how they prefer to receive documents like receipts and invoices. The businesses that have the best experience with full-service bookkeeping are the ones that establish clear communication habits early instead of waiting for problems to come up.
One thing people overlook is that the first month is also when you evaluate whether the relationship is a good fit. Does the bookkeeper explain things in a way you understand? Do they respond in a reasonable timeframe? Do they seem to genuinely understand how your business operates? These are things you can only assess once the work starts.
If you are working with a QuickBooks ProAdvisor in Chandler or anywhere else, the first month should feel like an investment. It takes more time and energy upfront than any month that follows. But when the foundation is built correctly, everything after that first month becomes routine. Your books get done on time, your reports are accurate, and you stop wondering whether your numbers are right.
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More Questions
How do I find a bookkeeper who understands my industry?
Look for a bookkeeper who can describe the specific chart of accounts and reports that matter for your type of business. Ask about their client base, check references from similar businesses, and pay attention to whether they ask about your operations or just your transaction volume.
Read answerWhat's the best way to handle retainage in bookkeeping?
Set up dedicated Retainage Receivable and Retainage Payable accounts in your chart of accounts, track balances by project, and review them monthly so nothing falls through the cracks at project closeout.
Read answerHow do I set up QuickBooks Online for my business?
Start by choosing the right plan, then focus on your chart of accounts, bank connections, and opening balances. These three areas determine whether QBO actually gives you useful financial data or just creates a mess you'll need to clean up later.
Read answerHow should a general contractor track costs per project?
Assign every expense to a job number and cost category in your accounting software as it happens. Break costs into labor, materials, subcontractors, and equipment so you can compare actual spending to your estimate and catch overruns early.
Read answerHow do I track tips and gratuities in my books?
Tips should be tracked through a tips payable liability account, not as revenue. Credit card tips flow through your bank and get cleared when paid out, while cash tips still need to be reported and run through payroll for tax purposes.
Read answerShould I use cash basis or accrual basis bookkeeping?
Most small businesses do well with cash basis bookkeeping. It's simpler and offers more tax flexibility. But if you carry receivables, manage inventory, or need to understand true monthly profitability, accrual basis gives you a much clearer picture.
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