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Brooke Benson Question
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How I Keep Long AI Projects from Losing the Plot

The workflow starts when a project grows beyond one conversation and approved decisions, file versions, or next steps become difficult to track. I begin by creating one active authority document. It is not a transcript of every discussion; it contains only the rules, definitions, methods, and structural decisions that currently control the project. Next, I label project files by status: active, working, superseded, or archived. I also state clearly which file is authoritative instead of expecting the AI to infer it from the filenames. As decisions are approved, I record them in the authority document or a change log. I include what was decided, why it was decided, what it affects, and whether it needs later review. This keeps the chat from becoming the only project record. For large deliverables, I divide the work into named stages. A spreadsheet project might move through architecture, data migration, calculations, validation, and publication. Each stage produces a separate file and has a clear completion check. When a conversation gets too long, I create a handoff prompt for the next chat. It includes: - the project goal; - the active authority files; - completed work; - approved decisions; - unresolved issues; - the next specific deliverable; - anything that should not be redesigned. I start the new conversation with that prompt and only the files needed for the next stage. Finally, I validate the output outside the chat. For Excel files, that means opening them in desktop Excel, checking formulas and errors, saving them, closing them, and reopening them. An AI-generated file is not finished until it passes that check. The core pattern is to record the authority, label the versions, log decisions, work in stages, create a clear handoff, and validate the result. Step-by-step: 1. I create one active authority document containing the project’s current rules, definitions, methods, and structural decisions. 2. I label each project file as active, working, superseded, or archived, and identify the authoritative file. 3. I record approved decisions in the authority document or a change log, including the decision, rationale, effects, and any need for later review. 4. I divide large deliverables into named stages, with a separate file and clear completion check for each stage. 5. I create a handoff prompt when a conversation becomes too long, covering the project goal, authority files, completed work, approved decisions, unresolved issues, next deliverable, and anything that should not be redesigned. 6. I begin the next conversation with the handoff prompt and only the files needed for that stage. 7. I validate the final output outside the chat—for Excel files, by opening them in desktop Excel, checking formulas and errors, saving, closing, and reopening them.

Christian Denton
  • ChatGPT
  • Microsoft Excel
  • Google Drive
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