business-monthly

Strategy Monthly Check-in

Purpose

Monthly check-in that reviews the quarterly Core Focus and Outcomes, sets monthly Outcomes, and breaks those outcomes into high-level project tasks. This is where strategy becomes actionable work.

Hard Gate

Do NOT jump straight to tasks. Monthly outcomes come first, tasks come from outcomes. If there are no quarterly files (core-focus.md and outcomes.md for the current quarter), suggest running business-quarterly first, or business-initial if nothing exists.

Checklist

1. Read shared references - Load ./references/file-structure.md and ./references/markdown-templates.md
2. Read existing files - business-plan.md, current quarter's core-focus.md and outcomes.md, and the previous month's files if they exist
   • If no quarterly files exist, stop and redirect to business-quarterly or business-initial
3. Previous month review - if prior month's outcomes.md and tasks.md exist:
   • Review what was targeted
   • Check off completed items
   • Ask about anything that stalled: "This didn't get done — is it still important, should it carry forward, or should we drop it?"
4. Quarterly pace check - Compare progress to date against quarterly outcomes
   • If in month 2 of quarter and only 20% through a quarterly outcome, flag it
   • Ask: "Are we on track, or do we need to adjust?"
5. Monthly Outcomes - For each relevant quarterly focus area, set 1–3 monthly outcomes
   • These should be achievable in ~30 days
   • Each should represent meaningful progress toward the quarterly target
   • Walk through one at a time with the user
6. Present and approve Outcomes - Show the full set; get buy-in before moving forward
7. Run reviewer - Dispatch ./reviewers/review-monthly.md to sense-check outcomes against quarterly goals
8. Save monthly outcomes.md - Save to strategy/{year}/Q{N}/{month-name}/outcomes.md
9. Monthly Tasks/Projects - Break each outcome into 2–5 high-level project tasks or milestones
   • Not daily to-dos; these are "chunks of work" that might take a few days to a week
   • Examples: "Interview 5 potential users", "Draft landing page copy", "Set up analytics tracking"
10. Present and approve Tasks - Show the full list; get buy-in
11. Save monthly tasks.md - Save to strategy/{year}/Q{N}/{month-name}/tasks.md
12. Route to weekly - Suggest a weekly check-in to break the month into weekly work

Process Details

Setting Monthly Outcomes

Start with the quarterly focus and outcomes as your anchor:

• "Your quarterly focus is [X] with an outcome of [Y by end of quarter]. What would meaningful progress look like this month?"
• If they say something vague ("make progress on it"): "Can you put a number or specific milestone on that? What would you be able to point to at the end of the month?"
• If they say something too ambitious for one month: "That sounds like a quarter's worth of work. What's the subset that fits in a month?"

Go one outcome at a time. Don't batch them.

Breaking Outcomes into Tasks

Help them think in projects, not to-dos:

• "To achieve [monthly outcome], what are the main chunks of work? Think projects or milestones, not individual tasks."
• Flag granular tasks: "Writing the email copy" is weekly/daily level. "Launch email campaign" is monthly level.
• Flag unmapped tasks: "How does this connect to your monthly outcomes?"

Key Principles

• Outcomes before tasks - Resist jumping straight to doing
• Monthly outcomes are stepping stones - They should clearly add up to quarterly targets
• Tasks are projects, not to-dos - Save granular work for weekly/daily check-ins
• Pace tracking continues - Flag drift from quarterly goals early
• Carry forward decisions - Don't silently move incomplete items; make a conscious choice about whether they stay, evolve, or drop
• One question at a time - Keep the conversation focused
• Everything chains upward - Monthly outcomes → Quarterly outcomes → Annual vision

File Structure

Save outputs using the nested directory structure from file-structure.md:

• strategy/{year}/Q{N}/{month-name}/outcomes.md - The monthly outcomes with supporting context
• strategy/{year}/Q{N}/{month-name}/tasks.md - The high-level monthly projects and milestones

Month directories use lowercase full names (e.g., january, february). Use the current date to determine the correct quarter and month path.