What documents should I give my AI assistant?

Give your AI assistant the documents a smart new team member would need to do the job, and nothing that's stale or contradictory. Chapter 2 of the book, Feeding the Brain, organises them into three tiers.

Tier 1: Constitution

Stable facts that rarely change and that every answer depends on:

• Project charter, goals, and success criteria
• Scope statement and known exclusions
• Stakeholder list with roles and what each person cares about
• Glossary of acronyms and internal terms
• Key constraints: deadlines, budget ceiling, approval rules

Tier 2: News

What's happened recently, updated weekly or more often:

• Recent meeting notes and decisions
• Current status, open risks, and issues
• Change requests and their outcomes

Tier 3: Library

Reference detail the assistant only needs sometimes:

• Detailed schedules or work breakdown structures
• Requirements, contracts, and technical specifications
• Past reports and lessons learned

Rules that keep the output accurate

1. One current version per document. Remove superseded copies so the assistant doesn't mix them up.
2. Put dates in file names for anything that changes, such as "Risk Register 2026-09-23".
3. Prefer text over images. Headings, lists, and labelled tables are easier for the AI to read than screenshots or diagrams.
4. Summarise very long documents into a short context brief and keep the full version in the Library tier.
5. Leave out what you shouldn't share. Check your organisation's policy first, and anonymise names or figures where needed. See Is it safe to share project data with AI tools?.

For more on organising documents for AI, read Scattered Project Documents? How to Fix Them for AI, Your Disorganized Knowledge Base Kills AI Productivity, and AI Doesn't Know Your Team or Stakeholders? Fix That.