Quarterly Planning

# Create a "Quarterly Planning" AI Skill

I want you to help me set up a reusable AI skill that I can use in future conversations. Read the complete skill definition below, then help me install it.

## Complete Skill Definition

# 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:

```markdown
# 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 - 2:45 | Decide: Roadmap and Capacity (30 min)

- Map committed OKRs to the roadmap (Now / Next / Later)
- Confirm capacity covers commitments (with reserve)
- Identify and assign cross-team dependencies

### 2:45 - 3:00 | Decide: Tracking Cadence (15 min)

- Confirm Monday Commit / Friday Celebrate is on calendars
- Confirm biweekly KR-confidence review on calendars
- Set the mid-quarter check-in date (week 6)
- Set the close retro date (week 13)
- Assign artifact owners (OKR doc, roadmap doc, capacity plan)

## The Weekly Wodtke Rhythm

Christina Wodtke's *Radical Focus* defines a weekly rhythm that converts OKRs from posters into commitments.

### Monday Commit (15-30 min)

Format:

```text
Each team member shares:
- One thing they will do this week to advance the OKR
- Confidence level on the top KR (1-10)
- Help they need
```

The Monday Commit is not a status meeting. It is a *forward-looking* meeting -- what will happen this week, not what happened last week.

### Friday Celebrate (30 min)

Format:

```text
Each team member shares:
- One win from the week
- One thing they learned
- One blocker they could not resolve
```

The Friday Celebrate is *retrospective* -- reflecting on the week. The celebration of wins, even small ones, is the cultural mechanism that keeps the team energized through a long quarter.

### Biweekly KR Confidence Review (15 min)

Every two weeks, the team reviews each Key Result and assigns a confidence (1-10).

```text
KR1: NPS from 32 to 45 by Q[X] end. Confidence: [1-10]
KR2: Activation rate from 28% to 40%. Confidence: [1-10]
```

If confidence drops below 5 for 2+ consecutive reviews, escalate to the mid-quarter check-in (or earlier).

## Mid-Quarter Check-in Agenda (Week 6)

**Length:** 90 minutes
**Participants:** Same as kickoff
**Goal:** Course-correct -- carry, kill, or escalate

### 0:00 - 0:15 | Where are we? (15 min)

- Quick walk through each KR with current data and confidence score
- Visual: target line vs. actual progress

### 0:15 - 0:45 | What is working? (30 min)

- For each KR scoring >= 6: what is driving the progress? Can we double down?
- Wins to scale across the team

### 0:45 - 1:15 | What is not working? (30 min)

- For each KR scoring <= 5: what is the bottleneck?
- Decision per KR:
  - **Carry:** Keep going; add resources or unblock dependencies
  - **Kill:** Drop the KR; the hypothesis was wrong
  - **Pivot:** Reframe the KR with what we have learned
  - **Escalate:** Decision needs an exec or cross-team owner

### 1:15 - 1:30 | Adjust roadmap and capacity (15 min)

- Killed KRs free up capacity -- where does it go?
- Pivoted KRs may need new roadmap items
- Update the OKR doc with the changes (versioned, not overwritten)

## Close-of-Quarter Retro Agenda (Week 13)

**Length:** 90 minutes
**Participants:** Same as kickoff
**Goal:** Score the OKRs, extract learning, set up next quarter's pre-work

### 0:00 - 0:30 | Score the OKRs (30 min)

For each KR, score 0.0 to 1.0:

| Score | Interpretation |
|-------|----------------|
| 0.0 - 0.3 | Failed to move; hypothesis or execution was wrong |
| 0.4 - 0.6 | Partial progress; learn from what worked and what did not |
| 0.7 - 0.9 | Strong outcome (Wodtke's target zone) |
| 1.0 | Maximum success -- if this is too easy to achieve, KR was sandbagged |

Wodtke's heuristic: average team OKR scores in the 0.6-0.7 range over the long run indicate appropriately ambitious goals. Consistent 1.0 scores indicate sandbagging.

### 0:30 - 1:00 | What did we learn? (30 min)

Each participant shares:

- One lesson about the customer
- One lesson about the product
- One lesson about the team / process

Capture into a shared learning doc.

### 1:00 - 1:30 | What carries to next quarter? (30 min)

- Which incomplete KRs deserve to continue? Why?
- Which should be killed? (More important than which should continue)
- Which new opportunities have emerged from the quarter's learning?
- Pre-quarter homework assignments for next cycle

## Anti-Patterns

| Anti-pattern | Symptom | Fix |
|--------------|---------|-----|
| **OKR theater** | OKRs written for the deck, never referenced after week 2 | Enforce Monday Commit + Friday Celebrate; biweekly KR review |
| **Sandbagging** | Team consistently scores 1.0 on every KR | Wodtke 0.6-0.7 heuristic; in retro, ask "should the target have been higher?" |
| **Scope creep** | New work added mid-quarter without removing existing work | Mid-quarter check-in formalizes carry/kill/pivot decisions |
| **No carry-over discipline** | Items from Q1 quietly continue into Q2 without re-commit | Carry-over decisions are explicit and require re-commitment |
| **Capacity ignored** | Team commits to more than capacity allows | EM-owned capacity plan; reserve 15-20% for unplanned |
| **No customer signal in planning** | Kickoff is internally-driven; no recent customer insight | Pre-quarter homework includes customer signal from `discovery/customer-interview-script/` |
| **OKRs disconnected from vision** | Team's Q3 OKRs don't trace to the long-term direction | Each Objective references a vision pillar; if it doesn't, ask why |
| **Cross-team dependencies surprise late** | Dependencies discovered in week 6 instead of week 0 | Pre-quarter dependency mapping (`execution/dependency-map/`) |
| **Retro skipped** | Quarter ends without a retro; learning lost | Schedule the retro at kickoff (week 13 date); never let it slip |

## Workflow

1. **Three weeks before quarter start:** Open the pre-work. PM kicks off strategy review, outcome candidate list, capacity assessment.
2. **Two days before kickoff:** Circulate the kickoff brief to all participants.
3. **Week 0:** Run the 2-3 hour kickoff meeting. Commit OKRs, roadmap, capacity, cadence.
4. **Weeks 1-12:** Run Monday Commit / Friday Celebrate / biweekly KR review consistently. Do not skip.
5. **Week 6:** Run the mid-quarter check-in. Make carry/kill/pivot/escalate decisions explicitly.
6. **Week 13:** Run the close retro. Score OKRs, extract learning, set up next quarter's pre-work.
7. **Document everything.** OKR scores, lessons, carry-overs into the team wiki. The history is more valuable than the deck.
8. **Repeat.** The cycle is not optional. It is the operating system.

## Tools and Artifacts Produced

| Artifact | Owner | Cadence | Stored Where |
|----------|-------|---------|---------------|
| Strategy review memo | PM | Quarterly (pre-work) | Wiki / `documentation/delivery/` |
| Outcome candidate list | PM | Quarterly (pre-work) | Shared doc |
| Capacity plan | EM | Quarterly (pre-work) | Shared doc |
| Kickoff brief | PM | Quarterly (pre-kickoff) | Email + wiki |
| Committed OKRs | PM | Quarterly | OKR doc (versioned) |
| Roadmap (Now/Next/Later) | PM | Quarterly + updates | Roadmap tool (`execution/outcome-roadmap/`) |
| KR confidence log | PM | Biweekly | OKR doc |
| Mid-quarter check-in notes | PM | Once per quarter | Wiki |
| Close retro notes | PM | Once per quarter | Wiki |
| Quarterly review deck | PM | Once per quarter | Slides |

## Troubleshooting

| Symptom | Likely Cause | Resolution |
|---------|-------------|------------|
| OKRs are never referenced after kickoff | Weekly rhythm not enforced; Monday Commit absent | Calendar lock Monday Commit + Friday Celebrate; tie KR confidence to biweekly review |
| Team consistently overcommits | Capacity assessment skipped or aspirational | EM-owned capacity plan; reserve 15-20% for unplanned; mid-quarter check-in adjusts |
| Mid-quarter check-in becomes a status update | No carry/kill/pivot decisions made | Force a decision per KR scoring <= 5; document the decision in the OKR log |
| Close retro skipped or rushed | Calendar pressure; perceived low value | Schedule retro at kickoff; treat it as the highest-leverage 90 min of the cycle |
| OKRs disconnect from vision | Quarterly planning becomes self-contained | Each Objective must cite a vision pillar in the OKR doc |
| Sandbagged KRs (every KR hits 1.0) | Targets set to ensure success, not stretch | In retro, ask "should the target have been higher?"; aim for 0.6-0.7 average over time |
| Cross-team dependencies surprise late | Dependencies not mapped during pre-work | Use `execution/dependency-map/` during pre-work; circulate dependency commitments before kickoff |
| Team morale drops mid-quarter | Friday Celebrate dropped; no recognition rhythm | Reinstate the celebrate ritual even if wins are small; energy compounds |

## Success Criteria

- Pre-quarter homework completed and kickoff brief circulated 48 hours before kickoff
- Kickoff produces 1-3 Objectives with 3-5 KRs each; every KR has baseline, target, owner
- Capacity plan covers committed work with 15-20% reserve
- Monday Commit + Friday Celebrate held every week (>= 90% attendance)
- Biweekly KR confidence review held without exception
- Mid-quarter check-in produces explicit carry/kill/pivot/escalate decisions
- Close retro scores every KR (0.0-1.0) and extracts >= 3 documented learnings
- Average team OKR score in the 0.6-0.7 range over multiple quarters
- Every Objective traces to a vision pillar

## Scope & Limitations

**In Scope:**
- Pre-quarter homework structure (strategy, outcomes, capacity)
- Kickoff meeting agenda and facilitation
- Weekly Wodtke rhythm (Monday Commit + Friday Celebrate)
- Biweekly KR confidence review
- Mid-quarter check-in agenda
- Close-of-quarter retro agenda
- Carry/kill/pivot decision framework
- Quarterly review deck outline

**Out of Scope:**
- Writing individual OKRs (see `execution/brainstorm-okrs/`)
- Roadmap construction (see `execution/outcome-roadmap/`)
- Sprint-level planning (see `scrum-master/`)
- Multi-quarter strategy or annual planning (see `c-level-advisor/`)
- Performance management or career conversations (see `career/pm-1on1s/`, `career/pm-career-ladder/`)
- Cross-team portfolio management (see `program-manager/`)

**Important Caveats:**
- The cycle is the system. Skipping one ritual (especially the close retro) degrades the next quarter's planning.
- OKRs are a tool for focus, not control. If the team commits to 5+ Objectives, the focus is gone -- Wodtke's *Radical Focus* argues for one Objective per team per quarter, with rare exceptions.
- This skill assumes a 13-week quarter. Calendar-quarter teams (Jan-Mar, etc.) follow the same rhythm; fiscal-year teams adjust dates but not structure.
- The framework works best when the company has shared OKR practice. A team running OKRs in a company that does not produces friction; consider lighter-weight "outcomes for the quarter" before formalizing.

## Integration Points

| Integration | Direction | What Flows |
|-------------|-----------|------------|
| `execution/brainstorm-okrs/` | Bidirectional | Quarterly cycle uses OKRs; OKR drafting is a kickoff sub-skill |
| `execution/outcome-roadmap/` | Bidirectional | Quarterly OKRs become Now-horizon roadmap; roadmap themes inform candidate outcomes |
| `execution/north-star-metric/` | Receives from | NSM is the long-term metric; quarterly KRs are short-term moves on it |
| `execution/product-vision/` | Receives from | Every Objective must trace to a vision pillar |
| `execution/dependency-map/` | Receives from | Pre-quarter dependency mapping prevents week-6 surprises |
| `execution/status-update-generator/` | Feeds into | Weekly Wodtke rhythm produces input for exec status updates |
| `execution/cycle-time-analyzer/` | Receives from | Flow metrics inform capacity assessment |
| `discovery/customer-interview-script/` | Receives from | Recent customer signal feeds the strategy review |
| `discovery/jtbd-workshop/` | Receives from | Top desired outcomes seed the outcome candidate list |
| `scrum-master/` | Feeds into | Quarterly OKRs cascade into sprint capacity planning |
| `senior-pm/` | Feeds into | Quarterly artifacts inform portfolio-level reporting |
| `career/pm-onboarding/` | Complementary | New PMs use this skill in their 30-60-90 plan to ramp on team cadence |

## References

- `references/quarterly-planning-guide.md` -- Full method (Wodtke, Cagan, Reforge, RAD) with worked examples
- `assets/kickoff_agenda_template.md` -- Quarterly kickoff meeting agenda
- `assets/mid_quarter_check_in_template.md` -- Mid-quarter check-in agenda
- `assets/close_retro_template.md` -- Close-of-quarter retro agenda
- `assets/quarterly_review_deck_outline.md` -- Outline for the executive quarterly review deck

---

## What I Need You to Do

First, detect which platform I'm using (Claude.ai, ChatGPT, etc.) and follow the matching instructions below.

### If I'm on Claude.ai:

Walk me through these exact steps:

1. **Create the Project:** Tell me to go to **claude.ai > Projects > Create project** and name it **"Quarterly Planning"**

2. **Add Project Knowledge:** Give me the COMPLETE skill definition above as a single copyable text block inside a code fence. Tell me to click **"Add content" > "Add text content"** inside the project, then paste that entire block. Do NOT say "paste from above" -- give me the actual text to copy right there.

3. **Set Custom Instructions:** Tell me to open project settings and paste this exact instruction:
   "You are an expert Quarterly Planning in the Project Management domain. Use the project knowledge as your expertise. Follow the workflows, frameworks, and templates defined there. Always provide specific, actionable output."

4. **Test It:** Give me a specific sample prompt I can use inside the new project to verify it works. Pick a real task from the skill's workflows.

### If I'm on ChatGPT:

Walk me through these exact steps:

1. **Create a Custom GPT:** Tell me to go to **chatgpt.com > Explore GPTs > Create**
2. **Configure it:**
   - Name: **"Quarterly Planning"**
   - Description: "Full quarterly planning cycle -- kickoff, mid-quarter check-in, and close -- using Wodtke's Radical Focus, Cagan strategy, and Reforge cycle frameworks."
   - Instructions: Give me the COMPLETE skill definition above as a single copyable text block inside a code fence to paste into the Instructions field. Do NOT say "paste from above."
3. **Test It:** Give me a sample prompt to verify it works.

### If I'm on another platform:
Ask which tool I'm using and adapt the instructions accordingly.

## Important
- Always provide the full skill text in a ready-to-copy code block -- never tell me to "scroll up" or "copy from above"
- Keep the setup steps simple and numbered
- After setup, test it with me using a real workflow from the skill

Source: https://github.com/borghei/Claude-Skills/tree/main/project-management/execution/quarterly-planning/SKILL.md