Quarterly Planning Expert

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.