^redacted‌ and I recorded an episode of The Intentional Owner on whether your business could survive without you for two weeks. Halfway through, I realized it works just as well as a diligence exercise. Most of the businesses we buy are built around the seller. The seller has also gotten very good at quietly handling problems, so the business looks steadier than it is. Asking "what would break if you left for two weeks?" usually gets a vague answer. The specific versions work better: - Who has keys and system access besides you? - Who sends the daily schedule or dispatch? - Where do customer escalations and negative reviews go? - Who approves pricing exceptions? (At Alpha Dumpsters we had a literal pricing book, and every exception still meant knocking on the sellers' door.) - Who runs payroll, and who reviews the inputs? - Who handles chargebacks, and who manages the ad spend? - What comes up only quarterly or annually, like sales tax, insurance renewals, and licensing, and who owns it? That last group is the one people miss. Kaustubh pointed out that those tasks rarely come up, but if one gets dropped, your contractor license can be suspended and you can't do any work. For those who've acquired, what broke first that you didn't catch in diligence?