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 meeting agenda, mid-quarter check-in agenda, close-of-quarter retro, and the weekly/biweekly tracking cadence that holds it all together.
The framework synthesizes four canonical sources. Christina Wodtke's Radical Focus (2016) defines the weekly Monday-commit / Friday-celebrate rhythm and the discipline of one OKR per quarter. Reforge's product strategy cycle frames quarterly planning as a forcing function for strategy choices. Marty Cagan's quarterly product strategy connects vision and roadmap to quarterly bets. And the RAD ritual (Reflect-Align-Decide) is the meeting format used inside the kickoff, mid-check, and close meetings.
When to Use
- Pre-quarter (2-3 weeks before quarter 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. Use the framework to 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 -- this skill resets the ritual.
The Quarterly Cycle
Week -3 -2 -1 0 1-5 6 7-12 13
| | | | | | | |
| Pre-quarter | Kickoff | Mid-quarter | Close
| homework | (start) | check-in | retro
| | | |
+---Reforge / Cagan-+--- Wodtke weekly Mon/Fri rhythm ---+
Pre-Quarter Homework (Weeks -3 to -1)
Three workstreams happen in parallel before the kickoff:
- Strategy review. Is the team's strategy still right? (Cagan's product strategy review)
- Outcome candidate list. What outcomes could the team commit to? (Pulled from
discovery/jtbd-workshop/,execution/north-star-metric/,execution/outcome-roadmap/) - Capacity assessment. What is the team actually capable of delivering? (Headcount, capacity, dependencies, on-call rotation)
Output: a 1-page kickoff brief delivered 48 hours before the kickoff meeting.
Kickoff Meeting (Week 0)
The 2-3 hour meeting that commits the quarter's OKRs, roadmap, and capacity plan. Run as a RAD session (Reflect-Align-Decide).
Tracking Cadence (Weeks 1-12)
The Wodtke weekly rhythm:
- Monday Commit. 15-30 min team huddle. Each person commits to what will move the OKR this week.
- Friday Celebrate. 30 min team huddle. Wins, learning, blockers.
Plus a biweekly review of confidence levels on each Key Result (1-10 scale).
Mid-Quarter Check-in (Week 6)
The 90-minute meeting that course-corrects. Review confidence, kill or carry over, address dependencies.
Close-of-Quarter Retro (Week 13)
The 90-minute meeting that scores the OKRs (0-1.0), extracts learning, and feeds the next quarter's pre-work.
Pre-Quarter Homework
The homework is the difference between OKR-as-aspiration and OKR-as-commitment. Skip the homework and the kickoff becomes a brainstorm rather than a commit.
Workstream 1: Strategy Review
Owner: PM (with EM and Design Lead)
Output: A 1-page "is our strategy still right?" memo.
Questions:
- Vision check. Does the current vision still hold? (Use
execution/product-vision/'s Vision Review Checklist) - NSM check. Is the North Star Metric still the right one? (See
execution/north-star-metric/) - Customer signal. What has changed in the customer's world in the last quarter? (Pull from
discovery/customer-interview-script/recent sessions) - Competitive signal. What competitor moves are worth responding to?
- Operational signal. What has changed inside the team or company (org changes, budget shifts, exec mandates)?
If any of these has materially shifted, the strategy review escalates to a strategy reset before kickoff -- which may require more than one kickoff meeting.
Workstream 2: Outcome Candidate List
Owner: PM
Output: A list of 5-10 candidate outcomes, each scored for impact and feasibility.
Sources:
- Top desired outcomes from the last
discovery/jtbd-workshop/ - Themes in the outcome roadmap (
execution/outcome-roadmap/) - Open bets carried from prior quarter
- Customer-feedback opportunities surfaced in
discovery/interview-synthesis/ - Reactive items (incidents, SLA misses, churn drivers) -- these are necessary but should not crowd the list
For each candidate, capture:
- The outcome statement (in Ulwick format from
discovery/jtbd-workshop/) - The hypothesis: "If we [X], then [outcome] will improve from [Y] to [Z]"
- Confidence (1-10) -- how confident are we in the hypothesis?
- Effort estimate (S/M/L/XL)
Workstream 3: Capacity Assessment
Owner: EM (with PM)
Output: A capacity plan in person-weeks.
Account for:
- Headcount at start and end of quarter (planned hires, planned departures)
- Holidays, PTO commitments
- On-call rotation overhead
- Maintenance and support load (typically 20-30%)
- Cross-team dependencies (
execution/dependency-map/) - Reserve for unplanned work (typically 15-20%)
Output: "We have X person-weeks of productive capacity for new work."
The Kickoff Brief
48 hours before kickoff, the PM circulates a 1-page brief:
# Q[X] [Year] Kickoff Brief
**Team:** [...]
**Strategy status:** Unchanged / Updated / Reset (see attached memo)
**Vision link:** [link]
**Last quarter's score:** [average OKR score 0-1.0]
## Candidate Outcomes (5-10)
| # | Outcome | Hypothesis | Confidence | Effort |
|---|---------|-----------|------------|--------|
| 1 | [...] | [...] | 7 | M |
| ... | ... | ... | ... | ... |
## Capacity
- Total person-weeks: [X]
- Reserved (maintenance, on-call, unplanned): [Y]
- Available for new work: [X-Y]
## Carry-overs from last quarter
| # | Item | Why incomplete | Recommendation |
|---|------|----------------|-----------------|
| 1 | [...] | [...] | Kill / Carry / Restart |
## Open questions for the kickoff
- [Decision needed 1]
- [Decision needed 2]
- [Decision needed 3]
Kickoff Meeting Agenda (Week 0)
Length: 2-3 hours (or 2 x 90 min) Participants: PM, EM, Design Lead, +/- exec sponsor, +/- key cross-functional partners Format: RAD (Reflect-Align-Decide) Materials: Kickoff brief; whiteboard or shared doc
0:00 - 0:15 | Reflect: Last Quarter (15 min)
- Quick review of last quarter's OKR scores
- Top 2 learnings from the close retro
- Carry-overs: any items the team has agreed to continue?
0:15 - 0:45 | Align: Strategy Context (30 min)
- Strategy review memo: still valid? changes needed?
- Vision sanity check: still inspiring? Roadmap items must trace to it.
- NSM context: where do we stand? what trend are we trying to move?
- Top customer/competitive signals from pre-work
0:45 - 1:15 | Reflect: Candidate Outcomes Review (30 min)
- PM walks through the 5-10 candidate outcomes
- For each: hypothesis, confidence, effort
- Open Q&A and challenge
1:15 - 1:30 | Break (15 min)
1:30 - 2:15 | Decide: Commit to OKRs (45 min)
- Vote on 1-3 Objectives (Wodtke: prefer 1)
- For each Objective: 3-5 Key Results
- Each Key Result has a baseline, target, and owner
- Apply the
execution/brainstorm-okrs/SMART validation