Bookkeeping you can actually trust
If you don't trust your numbers, every decision is a guess. The fix is rhythm, not better software.
Reconcile every month, by the 10th
Bank and credit card statements reconciled monthly, not 'when there's time.' Behind-the-books shops always make the worst financial decisions, because they're flying blind.
Hire a bookkeeper before a CFO
A part-time bookkeeper for $300 to $800 a month is the highest-ROI hire most small shops never make. Owners doing their own books at midnight is a leading cause of bad books.
Three reports, every month
P&L, balance sheet, cash flow statement. Glance at all three. You don't need to be an accountant to spot a trend going the wrong way.
Take your version of this question further
This is one operator-tested angle on the question. Your shop, your size, your trade, and your team change the answer. Ask your specific version inside Ask a Shop Owner to get a response grounded in how owners like you actually handled it.