OPE+ July 2025 | Page 22

OPERATIONS

15 Critical Questions to Ask During Bookkeeping

By Gerri Detweiler
YOU’ RE SITTING AT YOUR desk on a Sunday evening, staring at a pile of receipts and trying to make sense of the numbers. Payments are due Tuesday, payroll hits Friday, and you’ re honestly not sure if there’ s enough cash to cover both. Sound familiar?
Most OPE dealers and landscaping professionals are good at what they do: selling and servicing equipment or creating beautiful outdoor spaces. But accounting? That’ s definitely not why they got into this business.
Yet here’ s the truth: the businesses that thrive in the industry aren’ t always the ones with the prettiest showrooms or best crews. They’ re the ones whose owners have learned to extract real intelligence from their financial data and act on it.
If you’ re a pro at knowing how many hours it will take to install a retaining wall, but don’ t know your margins on the job, you have work to do.
The problem isn’ t that you’ re bad at business— it’ s that nobody ever taught you which questions to ask when you’ re doing your books. You enter transactions, reconcile accounts and file reports, but you’ re missing the strategic insights hidden in those numbers.
These 15 questions will help transform your bookkeeping from a boring chore into one of your best business tools.
Foundation Questions: Getting the Basics Right 1. Is my business structure actually working for me financially? Your business entity choice affects every dollar that flows through your company. If you’ re still operating as a sole proprietorship because you think it’ s simpler, you could be leaving money on the table and exposing yourself to unnecessary risk.
An LLC or corporation with S Corp tax election may save a profitable landscaping business thousands annually in selfemployment taxes, for example, when compared to one that operates as a sole proprietorship. Owners of businesses taxed as S Corps may be able to pay themselves a reasonable salary, which is subject to payroll taxes, and the rest as distributions, which are not. Ask an accountant to walk you through this option to make sure you comply with IRS rules.
2. Am I using the right accounting method for where my business is today? Cash-basis accounting works when you’ re starting out with simple transactions. But if you’ re an OPE dealer managing inventory and manufacturer relationships, or a landscaper with multiple ongoing projects, accrual accounting may provide a more accurate picture.
The danger of cash-basis? You might show zero revenue in May for a large installation that won’ t be paid until July, making that profitable month appear like a financial disaster. Again, consult an accounting professional to find out what’ s right for your business.
Daily Discipline Questions 3. What does my cash position look like right now? Here the key is to focus not on just your bank balance, but on whether your business has the money it needs to pay for immediate expenses. Check your cash flow summary daily, review accounts receivable aging, and monitor upcoming payables.
A daily cash pulse check allows you to spot problems before they become crises. Maybe that large customer payment is 10 days late with a payment, or you have an equipment loan payment due next week.
4. Are all my transactions captured and categorized correctly? Accounting software can import bank feeds automatically, but garbage in equals garbage out. Each transaction needs to go into the correct category in order to be useful and accurate.
For example: for a landscaper, this might mean separating“ Materials: Fertilizer” from“ Materials: Plants.” For equipment dealers, it means tracking“ Parts” revenue separately from“ Service” revenue.
These details aren’ t bookkeeping busy work— they’ re the foundation for understanding what actually makes you money. Key to this process is setting up your chart of accounts correctly from the beginning. Get help if you don’ t know how to do that.
Weekly Management Questions 5. How quickly am I converting work into cash? Get deposits or payments on the spot whenever possible. If not, send invoices immediately after job completion. Every day you delay invoicing is a day you’ re providing an interest-free loan to your customer.
Track your average collection time. If customers typically pay in 30 days, but you’ re invoicing two weeks after job completion, you could wait more than 44 days for your money.
6. What’ s the real story behind this week’ s numbers? Don’ t just record numbers, analyze them. If equipment sales are down but service revenue is up, what does that tell you about your market? If labor costs are higher than expected, is it overtime, inefficiency, or rate increases?
22 OPE + July 2025 www. OPE-Plus. com