Short answer: Audit your operation across five areas: process (what happens and who owns it), data (where it lives and how many copies exist), tools (what's used and what overlaps), people (what's manual and what's single-person dependent), and risk (what breaks if someone leaves). Work through each with the questions below and rank findings by frequency multiplied by pain.
Score each finding on frequency (how often it bites) and pain (time, money, or risk when it does). Multiply. Then sort into three tiers:
Turn the findings into a one-page current-state map and a ranked roadmap. Share both with the team — they'll correct things you got wrong, and their corrections are usually the most valuable part of the exercise.
Roughly a week of part-time effort for a business under thirty people, including team conversations.
Shadow systems — the personal spreadsheets and private boards. Founders consistently underestimate how many exist.
They should participate, but the interviews go better when someone else asks the questions. People soften answers when the founder is in the room.
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