Cowork Session Planner

Cowork Session Planner

This skill generates a pre-session brief for non-technical Cowork users by scanning available project files (context.md, logs, tasks, CLAUDE.md) and producing a minimal structured brief: current project status, recommended session goal, and a prioritised work plan. It runs at the very start of a session — before any real work task is requested — so the user knows exactly where to focus.

Input: Current workspace / project folder. Optional: explicit session goal as free text.

Output: Structured markdown brief (inline response). Optionally saved to output/session-brief.md on user request.

Language Detection

Detect the user's language from their message:

• If Russian (or contains Cyrillic): respond in Russian
• If English (or other Latin-script language): respond in English
• If ambiguous: respond in the language of the trigger phrase used

Instructions

Step 1: Parse Input

1. Check if the user provided an explicit session goal (free text after the trigger phrase).

   • If yes: store as stated_goal; use it as the primary session focus in Step 4.
   • If no: stated_goal is empty; derive focus from project files in Step 3.

2. Identify the project folder to scan.

   • Default: current workspace / selected folder.
   • If user specifies a path, use that path.

Step 2: Scan Project Files

1. Look for the following files in the workspace (in order of priority):

   • context.md or CLAUDE.md — project overview and status
   • logs/log.md — recent activity log
   • TASKS.md or any file containing open tasks
   • Any output/skill-spec.md or in-progress output files

2. For each found file, extract:

   • context.md / CLAUDE.md: project name, current status, open questions
   • logs/log.md: last log entry (date + action description)
   • TASKS.md: open tasks (status: pending or in_progress)
   • skill-spec.md: if present, note "skill spec in progress"

3. Note any missing files for the Notes section of the brief.

Edge Cases:

• If no context.md or CLAUDE.md found: proceed without project overview; flag as missing in Notes.
• If log file is empty or absent: skip last-action extraction; open brief with "No activity log found."
• If multiple task files found with conflicting state: list all sources; flag conflict in Notes.

Step 3: Determine Session Focus

1. If stated_goal is set: use it as the session goal. Skip to Step 4.

2. Otherwise, derive focus from extracted data:

   • Check open tasks (status: pending / in_progress) — select the highest-priority item.
   • If no tasks, check last log entry — infer next logical step from last completed action.
   • If neither available: propose "Define session goal" as the first task.

3. Compile a prioritised work list (max 5 items):

   • Item 1: derived or stated session goal
   • Items 2–5: remaining open tasks or logical next steps

Step 4: Assemble Brief

1. Build the pre-session brief with these sections:

   • Project / Status: project name + 1-sentence current state
   • Session Goal: recommended or stated goal (1 sentence)
   • Work Plan: numbered list, max 5 items
   • Blockers: any open blockers or conflicts from Step 2; "None" if clean
   • Notes: any missing files, file conflicts, or flags from Step 2

2. Use bilingual headers (EN + RU) if Russian was detected; English-only otherwise.

3. Display the brief inline. Do not save to file unless user explicitly requests it.

Step 5: Handle Save Request

1. If user says "save" or "save to file": write brief to output/session-brief.md.
2. Confirm file written and provide path.

Negative Cases

• No project files found (empty workspace): Return: "No project files found. Please select your project folder or provide a session goal to get started." Do not generate an empty or partial brief.
• User invokes mid-session (active tasks detected): Detect in-progress tasks or recent log entries (within last hour). Note: "It looks like you're already mid-session." Offer a re-focus brief instead of an initial brief (same format, but titled "Re-focus Brief").

Output Format

Inline markdown response:

## Сессионный бриф / Session Brief
**Проект / Project:** [project name or folder]
**Статус / Status:** [1-sentence current state]

### Фокус сессии / Session Goal
[Recommended or stated session goal — 1 sentence]

### План работы / Work Plan
1. [Task 1 — highest priority]
2. [Task 2]
3. [Task 3]
...

### Блокеры / Blockers
- [Blocker 1 if any, otherwise: None]

### Заметки / Notes
- [Missing files, conflicts, or flags — if any]

Field rules:

• Work Plan: 1–5 items; each item is a specific, actionable task (not a vague category)
• Blockers: specific obstacle or "None"
• Notes: only populated when something is flagged (missing file, conflict, mid-session detection)