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, settle the inputs below. When one is missing or vague and would change the result, ask about it; when it wouldn't, use a sensible default and say which one you used.