08/07/2026
𝐘𝐨𝐮𝐫 𝐂𝐓𝐎 𝐡𝐚𝐧𝐝𝐬 𝐢𝐧 𝐭𝐡𝐞𝐢𝐫 𝐧𝐨𝐭𝐢𝐜𝐞 𝐨𝐧 𝐚 𝐓𝐮𝐞𝐬𝐝𝐚𝐲.
𝐁𝐲 𝐓𝐡𝐮𝐫𝐬𝐝𝐚𝐲, 𝐧𝐨𝐛𝐨𝐝𝐲 𝐜𝐚𝐧 𝐭𝐞𝐥𝐥 𝐲𝐨𝐮 𝐡𝐨𝐰 𝐡𝐚𝐥𝐟 𝐲𝐨𝐮𝐫 𝐬𝐲𝐬𝐭𝐞𝐦𝐬 𝐚𝐜𝐭𝐮𝐚𝐥𝐥𝐲 𝐰𝐨𝐫𝐤.
He didn't do anything wrong.
He just built most of it in his head, tweaking things as problems came up, without ever writing down why he made the calls he did.
The documentation exists, technically.
It's half-finished, six months out of date, and missing every exception that actually matters in practice.
This is usually the moment a business discovers the gap between having systems and having systems anyone else can actually run.
Is your business profitable, or is it transferable?
They're not the same thing, and most owners don't find out which one they've built until someone senior tries to leave.
I wrote about this in Monday's newsletter (71% of small businesses run on the knowledge of one or two people, per NAIC research), but here's the quick version.
Three questions that tell you fast:
1️⃣ Could someone else explain why a decision was made, not just what the decision was?
2️⃣ Is the "why" documented anywhere, or only in someone's head?
3️⃣ If that person left today, how long before something breaks that nobody saw coming?
Most businesses fail all three.
The reason? Because nobody thought to ask until it was already hard to answer.
The fix is making sure the knowledge was never trapped in one person's head to begin with.
What would happen in your business if your most senior technical person gave notice tomorrow?
