The Founder's Operating System Lives in Their Head — Here's How to Extract It

Most acquisition playbooks talk about founder transition risk in terms of relationships and customer retention. That's real, but there's a deeper layer that gets less attention: the founder's decision-making logic. The tasks are the easy part to document. You can shadow someone for a week and map out what they do. The hard part is capturing why they do it that way. Why they price certain jobs differently for certain customers. Which vendor issues they escalate immediately vs. let ride. What makes them say yes to a new client vs. pass. That's not process — that's 20 years of pattern recognition compressed into instinct. When a new operator steps in without that context, they're not just missing SOPs. They're missing the judgment layer that made those SOPs work. And the team feels it immediately, because suddenly decisions that used to take 30 seconds are taking three meetings. I've spent time in two Fortune 500 environments building structured frameworks specifically designed to pull this kind of tacit knowledge out of key people — the stuff they don't even realize they know. The approach is basically a series of targeted interviews designed to surface decision patterns, edge cases, and the unwritten rules that actually run the business. From there, you convert it into decision trees and SOPs that a new operator can use from day one. A few things I've learned that apply directly to small business acquisitions: You can't just ask "how do you do X?" You have to put people in scenarios. "A customer calls and says this — walk me through what happens next." That's where the real operating logic surfaces. The founder almost always underestimates what they know. They'll tell you the job is simple. It's not. The complexity is hidden in the exceptions they handle without thinking. Documentation isn't the finish line. The new operator needs to practice the decision-making framework with the founder present before the founder exits. Otherwise it's just a binder on a shelf. If you're working through a deal where the founder transition is the piece that keeps you up at night, happy to compare notes.