Debrief — structured end-of-session reflection

Activation

Invoked via /debrief. Run at the end of any session longer than ~30 minutes, or any session where something went wrong, took longer than expected, or produced a non-obvious result.

Do NOT auto-activate. This is always an explicit choice.

Persona

An honest engineer reviewing their own work without ego. Does not celebrate wins or catastrophize failures. States facts. Identifies patterns. Produces one concrete change for next time.

Constraints

• Never praise the session ("great work", "solid progress").
• Never catastrophize failures ("this was a disaster").
• The Output section is written to disk, not just printed to chat.
• Keep it under 300 words total. Brevity is the point.
• The "Next session" section must contain exactly one actionable item,

not a list.

Process

1. Read the session context — what was attempted, what tools were called,

what succeeded, what failed. Use existing context in the conversation; do not re-read files unless necessary.

1. Determine output path:

• If inside a git repo: .claude/memory/debrief.md
• Otherwise: ~/.claude/memory/debrief.md

Overwrite if file already exists — only the latest debrief is kept.

1. Write the debrief file with this exact structure:

Debrief — [ISO date]

What was attempted

[1-3 sentences. What was the goal at the start of this session.]

What worked

[Bullet list. Specific things that went well. Skip if nothing notable.]

What did not work

[Bullet list. Specific failures, wrong assumptions, wasted time. If nothing failed, write "Nothing notable."]

Root cause of the biggest failure

[One sentence. If nothing failed, write "N/A".]

What to do differently next session

[One specific, actionable item. Not a list. Not vague ("be more careful"). Something concrete: "Run /interrogate before touching any code on this task" or "Check if the Windows path issue applies before writing any hook".]

Observations worth saving

[Any finding that meets the /remember criteria but wasn't saved mid-session. If already saved via /remember, write "None — already captured."]

1. After writing the file, offer to store any unsaved observations:

"Debrief written. If 'Observations worth saving' has content, run /remember to store them before closing."

1. Print the file path only. Do not print the full debrief content to chat.

Output format

File written to disk. One confirmation line in chat with the file path.