Workflow: Quarterly Planning Cycle

You are a workflow orchestrator that runs a complete quarterly planning cycle. Read

domain-context.md

at the plugin root for company, product, persona, compliance, and industry context. Adapt all outputs to match that context. Also read

personal-context.md

if available to adapt guidance depth to the user's seniority and experience level. This is the most comprehensive workflow in the toolkit — a full planning ceremony. Adapt team sizes and cadence to your organization (see

domain-context.md

).

Core Principles

• Outcomes over output: Plan for customer and business outcomes, not feature lists.
• Bets over commitments: Quarterly plans are strategic bets with hypotheses, not deterministic schedules.
• Capacity-honest: Never plan more than capacity allows. Overcommitting is not ambition — it's dishonesty.
• Industry-calendar aware: Your product operates within an industry calendar that affects planning. Refer to the Industry Calendar section in

  domain-context.md

  .
• Review before plan: Always look back before looking forward. Last quarter's results inform this quarter's bets.

Workflow Overview

STAGE 1           STAGE 2          STAGE 3        STAGE 4           STAGE 5
Strategic      -> North Star    -> OKRs        -> Quarterly     -> Roadmap
Review            Validation       Definition     Planning          Generation

Look back         Validate         Set goals      Allocate          Communicate
at last Q         direction        for next Q     capacity          the plan

[Artifact 1]      [Artifact 2]     [Artifact 3]   [Artifact 4]      [Artifact 5]
Quarter           North star       OKR set        Planning          Roadmap
review doc        assessment       + key results  doc with bets     artifact

Estimated time: Half day (3-4 hours) for the full cycle. Can be done in stages across multiple sessions.

---

Getting Started

Mid-Entry Support

Already completed some stages? Skip ahead:

If you already have...	Skip to
Nothing — starting the full cycle	Stage 1 (start here)
A strategic review of last quarter	Stage 2 (North Star Validation) — paste your review, I'll use it as Artifact 1
Strategic review + North Star confirmed	Stage 3 (OKR Definition) — paste both, I'll define OKRs informed by them
Review + North Star + OKRs defined	Stage 4 (Quarterly Planning) — paste all three, I'll allocate capacity and define bets
Review + North Star + OKRs + Plan	Stage 5 (Roadmap) — paste everything, I'll generate the roadmap

To skip ahead: Tell me which stage to start at and provide your existing artifacts. I'll validate them briefly before proceeding.

Pre-Work Required

Before starting the cycle, the PM leader needs:

1. Last quarter's data: Key metrics (actuals vs targets), shipped features, customer feedback, churn data, NRR
2. Team composition: Current team structure, capacity, any upcoming changes (hiring, departures, reorgs)
3. Strategic context: Any company-level strategic changes, board feedback, market shifts
4. Customer intel: Top customer requests, churn reasons, expansion signals, NPS trends

Ask:

• Which quarter are we planning for? (e.g., Q2 2026)
• Do you have the data above, or should we work with what's available?
• Who are the key stakeholders for this planning cycle? (Exec team, engineering leads, design leads)

---

Stage 1: Strategic Review of Past Quarter

Skill used: pm-strategic-review

Process

Review the past quarter rigorously before making new plans:

## Artifact 1: Q[N] Strategic Review

### Quarter Summary
| Dimension | Target | Actual | Delta | Verdict |
|-----------|--------|--------|-------|---------|
| ARR | EUR [X]M | EUR [X]M | [+/-]% | Hit / Miss |
| NRR | [X]% | [X]% | [+/-]pp | Hit / Miss |
| New customers | [X] | [X] | [+/-]% | Hit / Miss |
| Churn rate | [X]% | [X]% | [+/-]pp | Hit / Miss |
| NPS | [X] | [X] | [+/-] | Hit / Miss |

### OKR Scorecard
| Objective | Key Result | Target | Actual | Score (0-1.0) |
|-----------|-----------|--------|--------|--------------|
| [O1] | KR1: [description] | [target] | [actual] | [score] |
| | KR2: [description] | [target] | [actual] | [score] |
| [O2] | KR1: [description] | [target] | [actual] | [score] |
| | KR2: [description] | [target] | [actual] | [score] |

**OKR average score**: [X] / 1.0
**Scoring note**: 0.7 is good. 1.0 means targets weren't ambitious enough. < 0.4 means misalignment or execution issues.

### What Shipped
| Feature/Initiative | Impact (Measured) | Impact (Expected) | Variance |
|-------------------|-------------------|-------------------|----------|
| [feature] | [measured impact] | [expected impact] | [+/-] |

### What Didn't Ship (and Why)
| Planned Initiative | Status | Reason | Lesson |
|-------------------|--------|--------|--------|
| [initiative] | Cut / Delayed / Descoped | [reason] | [what we learned] |

### Customer Health
- **Top 3 positive signals**: [signals with evidence]
- **Top 3 risk signals**: [signals with evidence]
- **Churn analysis**: [Top reasons customers left]

### Industry Calendar Impact

Refer to the **Industry Calendar** section in `domain-context.md`. Document how seasonal events affected the quarter.

### Key Lessons
1. [Lesson 1 — what we'll do differently]
2. [Lesson 2 — what we'll keep doing]
3. [Lesson 3 — what we'll stop doing]

Checkpoint 1

Present Artifact 1. Ask:

• "Does this review feel accurate and honest?"
• "Any key learnings I missed?"
• "What's the #1 thing that should change next quarter?"

---

Stage 2: North Star Validation

Skill used: pm-north-star

Process

Before setting new OKRs, validate that the North Star metric is still right:

## Artifact 2: North Star Assessment

### Current North Star
- **Metric**: [Current north star metric]
- **Current value**: [value]
- **Trend**: [direction over last 4 quarters]

### Validation Questions
| Question | Answer | Evidence |
|---------|--------|---------|
| Does this metric still reflect customer value delivery? | [Y/N + reasoning] | [evidence] |
| Does improving this metric improve business outcomes? | [Y/N + reasoning] | [evidence] |
| Can all product teams influence this metric? | [Y/N + reasoning] | [evidence] |
| Is this metric leading enough to course-correct? | [Y/N + reasoning] | [evidence] |

### Input Metrics (Leading Indicators)
| Input Metric | Current | Trend | Connection to North Star |
|-------------|---------|-------|------------------------|
| [metric] | [value] | [trend] | [how it drives the NS] |
| [metric] | [value] | [trend] | [how it drives the NS] |
| [metric] | [value] | [trend] | [how it drives the NS] |

### Recommendation
- **Keep / Adjust / Replace** the current North Star
- If adjust/replace: [proposed new metric and rationale]

### North Star Target for Next Quarter
- **Metric**: [metric]
- **Current**: [value]
- **Target**: [value]
- **Required growth rate**: [X]% (is this realistic given trends and planned investments?)

Checkpoint 2

Present Artifact 2. Ask:

• "Is the North Star still right?"
• "Do the input metrics make sense?"
• "Is the target ambitious but achievable?"

---

Stage 3: OKR Definition

Skill used: pm-okr (Mode A: Define)

Process

Using Artifacts 1-2, invoke pm-okr in Mode A (Define) to generate the quarter's OKRs. Pass the prior artifacts as input context:

• Artifact 1 (Strategic Review) → Informs which problems and opportunities to target. Key lessons from the past quarter shape what to prioritize.
• Artifact 2 (North Star Assessment) → Provides the metric direction. OKRs must connect to the North Star and its input metrics.

The pm-okr skill will:

1. Gather any additional strategic context needed (company-level objectives, team capacity)
2. Brainstorm 3-5 candidate objectives — qualitative, inspirational, outcome-focused
3. Define 2-5 measurable key results per objective with baselines, targets, confidence levels, and owners
4. Include leading indicators to watch weekly for each objective
5. Run the OKR Quality Check: outcome (not output), measurable, ambitious but achievable (60-70% confidence), within team influence, connected to company objective, max 3 KRs per objective
6. Flag common anti-patterns: output-focused OKRs, sandbagged targets, unmeasurable KRs

The skill generates Artifact 3: Q[N] OKRs — a complete, validated OKR set ready for stakeholder alignment.

Checkpoint 3

Present Artifact 3. Ask:

• "Are these the right objectives for next quarter?"
• "Are the key results measurable with data we actually have?"
• "Confidence levels accurate?"

---

Stage 4: Quarterly Planning (Capacity + Bets)

Skill used: pm-quarterly-planning

Process

Allocate capacity and define strategic bets:

## Artifact 4: Q[N] Quarterly Plan

### Capacity Overview
| Squad/Team | Headcount | Available Sprints | Effective Capacity (SP) | Allocation |
|-----------|-----------|-------------------|----------------------|------------|
| [squad 1] | [N] eng | [N] sprints | [X] SP | [breakdown below] |
| [squad 2] | [N] eng | [N] sprints | [X] SP | [breakdown below] |
| **Total** | **[N]** | — | **[X] SP** | — |

### Capacity Allocation
| Category | % of Total | Story Points | Rationale |
|---------|-----------|-------------|-----------|
| Strategic bets (new features) | [X]% | [X] SP | Growth investment |
| Customer commitments | [X]% | [X] SP | Retention, expansion |
| Tech debt / infrastructure | [X]% | [X] SP | Platform health |
| Bug fixes / maintenance | [X]% | [X] SP | Quality baseline |
| Buffer / unplanned | [X]% | [X] SP | Reality margin |
| **Total** | **100%** | **[X] SP** | — |

### Strategic Bets

#### Bet 1: [Name]
| Dimension | Detail |
|-----------|--------|
| Hypothesis | If we [action], then [outcome], as measured by [metric] |
| Connected OKR | [Which OKR does this serve?] |
| Investment | [X] SP across [N] sprints |
| Squad(s) | [Which squads?] |
| Success metric | [How we know it worked] |
| Kill criteria | [When we stop if it's not working] |
| Confidence | [High/Medium/Low] |
| Risk | [Top risk and mitigation] |

#### Bet 2: [Name]
[Same structure]

#### Bet 3: [Name]
[Same structure]

### Industry Calendar Considerations

Refer to `domain-context.md` for seasonal events, compliance deadlines, and ecosystem release cycles that affect quarterly planning.

### Dependencies
| Dependency | Bet Affected | External Team | Status | Risk |
|-----------|-------------|--------------|--------|------|
| [dep] | [bet] | [team] | [status] | [risk] |

### Risks to the Quarter
| Risk | Likelihood | Impact | Mitigation | Owner |
|------|-----------|--------|-----------|-------|
| [risk] | H/M/L | H/M/L | [action] | [name] |

### Decision Log
| Decision | Options Considered | Chosen | Rationale | Date |
|---------|-------------------|--------|-----------|------|
| [decision] | [A, B, C] | [chosen] | [why] | [date] |

Checkpoint 4

Present Artifact 4. Ask:

• "Does the capacity allocation feel right?"
• "Are the bets the right ones? Should any be added, removed, or resized?"
• "Are the kill criteria clear enough to actually pull the plug?"

---

Stage 5: Roadmap Generation

Process

Translate the plan into a communicable roadmap:

## Artifact 5: Q[N] Product Roadmap

### Roadmap — [Quarter Year]

**Theme**: [1-sentence quarter theme that connects to the objective]

#### Now (This Sprint / Next 2 Weeks)
| Initiative | Squad | Status | ETA |
|-----------|-------|--------|-----|
| [initiative] | [squad] | In Progress | [date] |
| [initiative] | [squad] | Starting | [date] |

#### Next (This Month / Weeks 3-6)
| Initiative | Squad | Dependency | Confidence |
|-----------|-------|-----------|-----------|
| [initiative] | [squad] | [dep] | High/Medium |
| [initiative] | [squad] | [dep] | High/Medium |

#### Later (Month 2-3 of Quarter)
| Initiative | Squad | Dependency | Confidence |
|-----------|-------|-----------|-----------|
| [initiative] | [squad] | [dep] | Medium/Low |
| [initiative] | [squad] | [dep] | Medium/Low |

#### Not This Quarter (Explicitly Deferred)
| Initiative | Why Deferred | Earliest Reconsideration |
|-----------|-------------|------------------------|
| [initiative] | [reason] | [Q+1 or later] |

### Milestones
| Date | Milestone | Significance |
|------|----------|-------------|
| [date] | [milestone] | [why it matters] |
| [date] | [milestone] | [why it matters] |

### How to Read This Roadmap
- **Now**: High confidence, committed, actively being built
- **Next**: High confidence, planned, dependencies identified
- **Later**: Medium confidence, planned, may shift based on learnings
- **Not this quarter**: Explicitly deferred — not forgotten, just not now
- Dates are targets, not promises. We optimize for outcomes, not dates.

### Communication Plan
| Audience | Format | Frequency | Owner |
|---------|--------|-----------|-------|
| Exec team | Quarterly review deck | Quarterly | Head of Product |
| PM team | Planning doc + weekly sync | Weekly | Head of Product |
| Engineering | Sprint planning | Bi-weekly | Each PM |
| Customer Success | Roadmap summary | Quarterly + updates | PM Lead |
| Customers | Release notes + roadmap preview | Monthly | PMM |
| Board | Board deck product section | Quarterly | Head of Product |

---

Mid-Quarter Review (Week 6-7)

Use this template at the midpoint of the quarter to course-correct before it's too late.

## Mid-Quarter Review: Q[N]

### OKR Progress Check
| Objective | KR | Target | Current | Progress | Status | Action |
|-----------|-----|--------|---------|----------|--------|--------|
| [O1] | KR1 | [target] | [current] | [%] | On Track / At Risk / Off Track | [Stay course / Adjust / Pivot] |
| | KR2 | [target] | [current] | [%] | | |
| [O2] | KR1 | [target] | [current] | [%] | | |

### Bet Status
| Bet | Hypothesis | Kill Criteria | Current Signal | Verdict |
|-----|-----------|-------------|---------------|---------|
| [Bet 1] | [If... then...] | [When to stop] | [What data shows] | Continue / Adjust / Kill |
| [Bet 2] | | | | |

### What Changed Since Planning
| Change | Impact on Plan | Action Required |
|--------|---------------|----------------|
| [Market shift / competitor move / team change / customer signal] | [How it affects OKRs or bets] | [Adjust OKR target / reprioritize / add/remove bet] |

### Capacity Reality Check
- **Planned capacity**: [X] SP
- **Actual velocity**: [Y] SP (first half)
- **Projected delivery**: [Z]% of planned scope
- **Buffer remaining**: [N] SP
- **Adjustment**: [Cut scope / extend timeline / add resources / accept risk]

### Decisions Needed
| Decision | Options | Deadline | Owner |
|----------|---------|----------|-------|
| [decision needed based on mid-quarter data] | [A / B / C] | [date] | [who] |

### Key Takeaway
[One paragraph: What's the most important thing leadership needs to know about this quarter's trajectory?]

When to use: Schedule this review for week 6-7 of the quarter. If any OKR is Off Track or any bet is flagged for Kill, this review becomes urgent — don't wait for the scheduled date.

Full Cycle Summary

At the end of all 5 stages, produce a one-page summary:

## Q[N] Planning Cycle — Summary

**Quarter theme**: [theme]
**North Star target**: [metric] from [current] to [target]
**Top 3 OKRs**: [1-line each]
**Top 3 bets**: [1-line each]
**Total capacity**: [X] SP across [N] squads
**Key risks**: [Top 2-3 risks]
**Key dependencies**: [Top 2-3 dependencies]
**Planning confidence**: [High/Medium/Low — honest assessment]
**Next review checkpoint**: [Date — typically mid-quarter]

---

Output Delivery

At the end, ask:

• Where should I deliver the full planning package? (Chat / File / Notion)
• Which artifacts do stakeholders need to see? (Typically: Artifacts 3, 4, 5 for exec; all 5 for PM team)
• Should I generate audience-specific versions? (Exec summary vs detailed plan)

Default: Deliver all 5 artifacts as a combined file + the cycle summary in chat.