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Module 4 · Lesson 4.5 · 13 min

Managing Long Sessions

Keep answers sharp in long working sessions using /context, /compact, /clear and a simple handover note.

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Module 4
Your Business Brain

Write your business down once. Every session starts knowing it.

Bruno Ashford
Bruno Ashford · Module 401 / 12
The problem
On Monday it wrote in your voice. On Tuesday it had never heard of you.
Bruno Ashford
Bruno Ashford · Module 402 / 12
Why AI forgets

The context window is a desk

If it is not on the desk, Claude does not know it.

  • Every session starts with a clear desk
  • Files, messages and replies fill it
  • When it is full, quality drops
  • /context shows what is on it
Bruno Ashford · Module 403 / 12
Two kinds of memory

What carries over between sessions

CLAUDE.mdAuto memory
Who writes itYouClaude
What it holdsInstructions and factsLearnings and preferences
LoadedEvery sessionEvery session
Edit with/memory or any editor/memory
Bruno Ashford · Module 404 / 12
The handbook

What goes in your CLAUDE.md

  1. 1CompanyWho we are in one paragraph
  2. 2OffersWhat we sell and for how much
  3. 3ClientsWho we serve and who we do not
  4. 4VoiceConcrete rules, real examples
  5. 5Red linesWhat never happens
  6. 6Folder mapWhere everything lives
Bruno Ashford · Module 405 / 12
Guidance from Anthropic's docs

Keep the handbook lean

~200lines per CLAUDE.md, recommended ceiling
1rule per line
@imports for longer documents
Bruno Ashford · Module 406 / 12
Rules

Red lines, standards, quality bars

Three different jobs. Write them separately.

  • Red lines: must never happen
  • Standards: how we always do it
  • Quality bars: checked before you see it
  • Test every red line by breaking it
Bruno Ashford · Module 407 / 12
Guidance vs. enforcement
CLAUDE.md guides the agent. Permissions and hooks lock the door.
Bruno Ashford
Bruno Ashford · Module 408 / 12
Folders

If a new hire could find it, so can the agent

Structure is context you never have to type.

  • One folder per business area
  • Dates first: 2026-09-proposal.md
  • Originals never edited
  • A folder map in CLAUDE.md
Bruno Ashford · Module 409 / 12
Long sessions

Four commands that keep answers sharp

  1. 1/contextSee how full the desk is
  2. 2/compactSummarise and keep going
  3. 3/clearFresh start between tasks
  4. 4Handover noteSave decisions to a file
Bruno Ashford · Module 410 / 12
Your project

A tested company handbook

Write it, then prove it on three real tasks.

  • Loaded and visible in /context
  • Knows your client, offer and voice
  • Refuses two red-line tests
  • Under about 200 lines
Bruno Ashford · Module 411 / 12
Recap
Stop re-explaining your business. Write it down once, and let every session start from there.
Bruno Ashford
Bruno Ashford · Module 412 / 12
01 / 12

Use ← → to move. The marker highlights text and the pencil draws on the slide; navigation locks while you annotate. Undo removes the last mark, Esc exits.

1Check the desk regularly

Run /context when a session has been going for a while or answers start to drift. If the context is mostly full, it is time to act, before quality drops.

Terminal
/context
2Compact when you are mid-task

/compact summarises the conversation so far and frees space, while keeping the thread of the task. You can tell it what to keep. Claude Code also compacts automatically when the window gets full, but doing it yourself at a natural break gives you control over what is kept.

Terminal
/compact Keep the pricing decisions, the client list we agreed and the open questions. Drop the drafts we rejected.
3Clear between unrelated tasks

Finished the sales analysis and starting on a marketing email? Type /clear. A clean start is faster, cheaper and more accurate than dragging the old task along. Your CLAUDE.md loads again automatically.

Terminal
/clear
4Write a handover note before you stop

Anything said only in conversation can be lost. At the end of a long task, ask Claude to write a short handover note to a file, and to move lasting rules into CLAUDE.md. Tomorrow you start from the note, not from memory.

Prompt for Claude
We are stopping for today. Write a handover note to reports/handover.md: what we did, decisions made, files created, open questions and the next three steps. Then tell me if any of today's decisions should become permanent rules in CLAUDE.md.
5Pick up where you left off

Claude Code can resume earlier conversations, and a handover file makes any fresh session productive in one message. For most business work, a fresh session plus the note beats resuming a huge old conversation.

Terminal
claude --continue
MDCompany CLAUDE.md TemplateTemplateMDAgent-Friendly Folder Structure GuideGuide

You have probably noticed it. The first hour with Claude is brilliant. By the third hour, it repeats itself, forgets a decision you made at lunch and starts to feel slower. That is not fatigue. It is a crowded desk.

Long sessions fill the context window with old files, old drafts and dead ends. The fix is a few simple habits: check the desk, summarise it when it gets full, start fresh between tasks, and save important decisions somewhere permanent.

Key points

  • Long sessions crowd the context and quality drops.
  • /context shows how full the desk is.
  • /compact summarises and frees space mid-task.
  • /clear starts fresh between unrelated tasks.
  • Save decisions in a handover note or CLAUDE.md, not only in chat.

Avoid

  • Running one conversation all day across unrelated tasks.
  • Making important decisions only in chat and never writing them down.
  • Waiting for answers to go bad before checking /context.
  • Resuming a huge old session when a fresh one plus a note would be better.
Real-world example: an e-commerce store

Priya spent a full afternoon with Claude rebuilding her product descriptions for 120 items. Around item 70 the tone started drifting back to generic. She ran /context, saw the window was nearly full of old drafts, and ran /compact asking it to keep the approved voice examples. Quality came back immediately. She now writes a handover note after every batch of 30 and starts the next batch fresh.

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