Quarterly Planning Expert

Overview

Quarterly planning is the operating cadence that turns annual strategy into quarterly outcomes. Done well, it produces aligned OKRs, a roadmap that delivers them, a capacity plan that respects reality, and a tracking ritual that catches drift before it compounds. Done poorly, it produces OKR theater -- a slide deck of objectives that nobody references after week two.

This skill is the above-OKR-writing companion to execution/brainstorm-okrs/. Where brainstorm-okrs/ covers how to write good OKRs, this skill covers the full quarterly cycle around them: pre-quarter homework, kickoff agenda, mid-quarter check-in, close-of-quarter retro, and the weekly/biweekly tracking cadence. The framework synthesizes four sources: Wodtke's Radical Focus (Monday-commit / Friday-celebrate rhythm, one OKR per quarter), a product strategy cycle (explicit upstream strategy choices), Cagan's quarterly product strategy, and the RAD ritual (Reflect-Align-Decide) used inside each meeting.

Core Capabilities

• Pre-quarter homework -- strategy review, outcome candidate list, capacity assessment, and the 1-page kickoff brief
• Kickoff facilitation -- the 2-3hr RAD agenda that commits OKRs, roadmap, and capacity
• Weekly Wodtke rhythm -- Monday Commit, Friday Celebrate, biweekly KR confidence review
• Mid-quarter check-in -- carry / kill / pivot / escalate decisions at week 6
• Close retro -- 0.0-1.0 OKR scoring, learning extraction, and next-cycle seeding

Clarify First

Before running a phase, confirm these inputs. If any is unknown or vague, ASK — do not assume:

• Which phase — pre-quarter/kickoff vs mid-quarter check-in vs close retro (selects the agenda and artifacts produced)
• Position in the 13-week cycle — what week you're in (the carry/kill/pivot check belongs at ~week 6, the retro at week 13)
• Existing OKRs & strategy — the committed Objective and the annual strategy it serves (the kickoff commits OKRs; every Objective must trace to a vision pillar)
• Real team capacity — honest capacity after PTO/on-call (a stretch slate dressed as commitments is the #1 cadence failure)

Stop rule: ask only the 2-3 that most change the output. If the user says "just draft it," proceed and list your assumptions at the top of the artifact.

The Quarterly Cycle

Week -3   -1     0       1-5    6      7-12    13
  | Pre-quarter | Kickoff |  Mid-quarter  | Close
  |  homework   | (start) |   check-in    | retro
  +-Strategy/Cagan--+-- Wodtke weekly Mon/Fri rhythm --+

• Pre-quarter (weeks -3 to -1): run the homework and kickoff to commit OKRs and roadmap.
• Mid-quarter (~week 6): run the check-in to course-correct.
• Close (week 13): run the retro to extract learning before the next cycle.

When to Use

• Pre-quarter (2-3 weeks before start). Run the homework and kickoff to commit OKRs and roadmap.
• Mid-quarter (~week 6 of 13). Run the mid-quarter check-in to course-correct.
• Close-of-quarter (last week). Run the close retro to extract learning before next planning cycle.
• New PM joining mid-quarter. Understand where the team is in the cycle and what is expected when.
• Failing OKR cadence. Team has OKRs but no one references them by week 4 -- reset the ritual.

References

Load the reference that matches the task -- keep this file lean and pull detail on demand:

• references/cycle-playbook.md -- the full operational playbook: pre-quarter homework + kickoff brief template, kickoff / mid-quarter / close agendas, the weekly Wodtke rhythm scripts, anti-patterns, artifacts-produced map, troubleshooting, and success criteria. Read this when running any phase of the cycle.
• references/quarterly-planning-guide.md -- the framework theory (Wodtke Radical Focus, Cagan product strategy, strategy cycle, RAD ritual) with a worked Reconcile Q3 example. Read this when you need the reasoning behind the rituals.
• references/red-flags.md -- 11 quarterly-planning anti-patterns (OKR theater, capacity in story points, stretch goals as committed slate) with symptoms and fixes. Read this when reviewing a quarter's plan or diagnosing a failing cadence.

Templates live in assets/: kickoff_agenda_template.md, mid_quarter_check_in_template.md, close_retro_template.md, quarterly_review_deck_outline.md.

Scope & Limitations

In scope: pre-quarter homework (strategy, outcomes, capacity); kickoff agenda; weekly Wodtke rhythm; biweekly KR confidence review; mid-quarter check-in; close retro; carry/kill/pivot framework; quarterly review deck outline.

Out of scope: writing individual OKRs (execution/brainstorm-okrs/); roadmap construction (execution/outcome-roadmap/); sprint-level planning (scrum-master/); multi-quarter / annual strategy (c-level-advisor/); performance management (career/); portfolio management (program-manager/).

Caveats: the cycle is the system -- skipping one ritual (especially the close retro) degrades the next quarter; OKRs are a tool for focus, not control (Wodtke argues one Objective per team per quarter); the skill assumes a 13-week quarter; it works best where the company has shared OKR practice.

Integration Points