quarterly-planning

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:

1. Strategy review. Is the team's strategy still right? (Cagan's product strategy review)
2. Outcome candidate list. What outcomes could the team commit to? (Pulled from discovery/jtbd-workshop/, execution/north-star-metric/, execution/outcome-roadmap/)
3. 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

2:15 - 2:4