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Annual Strategy Sprint

Workflow
5 steps·45 min·advanced

Build a 2-year product strategy your team can actually align on — vision, horizons, trade-offs, and a pre-mortem.

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Steps

1

Product Vision

Defining a Strong Product Vision

You are a product strategy advisor helping a PM craft a product vision that is both inspiring and actionable. Guide me through building a vision for [Type your product].

## Context
- **Current product stage:** {{product_stage}}
- **Target customer:** {{target_customer}}
- **Time horizon:** {{time_horizon}}

## Vision Building Framework

### 1. Customer Problem (The "Why")
- What fundamental problem does this product solve?
- Why does this problem matter now more than before?
- What is the cost of the status quo for the customer?

### 2. Future State (Working Backwards)
- Describe the world 3-5 years from now if this product fully succeeds
- Write a fictional customer testimonial from that future
- What behavior change does this product create?

### 3. Unique Value Proposition
- What makes this approach fundamentally different from alternatives?
- What would be lost if this product did not exist?
- What is the "10x better" dimension vs. status quo?

### 4. Strategic Guardrails
- What this product will NOT do (anti-goals)
- Which customer segments are intentionally excluded?
- What principles guide trade-off decisions?

## Output Format

### Vision Statement (1-2 sentences)
- Lofty and inspiring, yet realistic and attainable
- Focused on the customer outcome, not the technology
- Free of jargon — anyone in the company should understand it

### Vision Narrative (200-300 words)
- Tells the story: problem today, transformation, future state
- Includes the "why now" and "why us"

### Validation Checklist
Rate the vision against these 4 criteria (pass/fail):
1. Is it inspiring enough that the team wants to build it?
2. Is it realistic enough that stakeholders believe it?
3. Is it constraint-free (describes the outcome, not the solution)?
4. Is it grounded in a real user problem with evidence?
Customize Variables0/4
Start with a vision that's specific enough to guide real tradeoffs.
2

Strategy Blocks

Run a Strategy Blocks sprint to craft a 2-year product strategy

You are a senior product strategist helping me run a Strategy Blocks sprint for {{product_or_company}}. Our current business constraint is {{top_business_constraint}} and we have roughly {{weeks_available}} weeks before we need leadership alignment.

Walk me through all five steps of the small "s" 2-year strategy process and produce the concrete artifacts below. Wherever I need to fill in data, ask me one question at a time instead of guessing.

## Step 1 — Preparation (3-5 weeks)
1. Define the strategy working group roles: product lead (me), engineering lead, design lead, data lead. List the exact deliverable you expect from each.
2. Draft the leadership interview script — 5 questions per interview, covering success/failure, success metrics, principles, why things failed before, and pet ideas.
3. Give me a competitive + comparables template: head-to-head feature matrix, investment themes, screenshots.
4. Checklist for behavioral insights (data lead) and UXR insights (design/research).

## Step 2 — Strategy Sprint (1 week, day-by-day)
- Day 1: share-out agenda (list which sections each working group member presents)
- Day 2: problem generation to strategic pillar selection
  - How to cluster 50-150 problem statements into 10-15 themes
  - How to flip each cluster into an opportunity framing
  - Score each opportunity on: expected impact, certainty of impact, clarity of levers, uniqueness of levers (1-5 each)
  - Sum and sort; pick top 3 opportunity areas as the strategic pillars
  - Generate 3 "how might we" questions per pillar
- Day 3: 2-year winning aspiration
  - Imagine a journalist's headline two years from now — produce 3 draft headlines, then blend into one

## Step 3 — Design Sprint (1 week)
List what the design lead needs to produce: illustrative concepts per pillar that clarify strategy, not shovel-ready specs.

## Step 4 — Document Writing (1-2 weeks)
Outline the strategy document: context, 3 strategic pillars with rationale, what we're explicitly NOT focusing on, 2-year winning aspiration, illustrative concepts, success metrics.

## Step 5 — Rollout (2-3 weeks)
1. Gatekeeper 1:1s (founders/CEO)
2. Group review with functional leaders
3. Team roadshows (8-10 people, clarity adjustments only — defend pillars)
4. Empower teams to build roadmaps from the doc

## Output
Produce:
1. A filled-in 2-page strategy brief for {{product_or_company}}
2. The 4-dimension scoring rubric as a table
3. A kickoff agenda I can send to the working group on day 1
4. A sequenced list of the 3 biggest risks that could derail this process and how to pre-empt each

Default to concrete examples over abstract frameworks. Flag any step where my {{top_business_constraint}} changes the recommended approach.
Customize Variables0/3
Turn the vision into a 2-year strategy built on blocks, not slides.
3

Three Horizons Map

Build a three-horizons product strategy map

You are a product strategist helping me build a three-horizons strategy map for {{product_name}} over the next {{planning_window}}. Current revenue and growth profile: {{current_profile}}.

## Output a map with 3 rows
- **Horizon 1 (0-12 months) — Defend and extend the core.** List 3 bets, each with expected impact on {{north_star_metric}} and guardrail metrics.
- **Horizon 2 (12-24 months) — Adjacent growth.** List 2 bets with the market hypothesis and the proof point required before funding.
- **Horizon 3 (24-36+ months) — Transformative.** List 1-2 bets with the technology or customer behavior shift that has to be true.

## For each bet
1. Cost (eng weeks + non-eng cost)
2. Expected upside and the confidence level
3. Kill criteria — the specific metric thresholds that trigger wind-down
4. Owner

## Resourcing mix
Recommend a % split across horizons for {{product_name}}'s stage and defend it with 2 comparables.
Customize Variables0/4
Balance core, adjacent, and transformational bets explicitly.
4

What We Are NOT Doing

Design a "what we are NOT doing" document

You are a product strategist helping me write a "What We Are NOT Doing" document for {{team_or_product}} covering {{time_horizon}}. My three biggest recurring scope debates: {{recurring_debates}}.

## Format per entry
For each item we are NOT doing:
1. **The ask** — who asked for it, in one sentence
2. **Why it's attractive** — steelman the case in 2-3 sentences
3. **Why we are not doing it** — pick one of: wrong time (what trigger would flip this), wrong team (whose job is this), wrong strategy (the pillar it violates), wrong evidence (what data we'd need)
4. **Revisit trigger** — the specific event or metric threshold that re-opens the debate
5. **Owner** — who updates this entry if things change

## Output
1. Filled entries for each of the recurring debates
2. Three items I probably should add but haven't thought of — based on the strategic pillars
3. The single entry most likely to get challenged at the next QBR and the prepared response

## Distribution plan
Where this doc lives, who reviews it quarterly, and the review cadence for revisit triggers.
Customize Variables0/3
Write down the tempting ideas you're rejecting. It's how strategy survives Q2.
5

Pre-Mortem

Run a pre-mortem on your annual product plan

You are a strategy facilitator running a pre-mortem on {{plan_name}} for {{planning_year}}. The current plan commits us to: {{top_commitments}}.

## Step 1 — Imagine year-end failure
Assume it is 12 months from now and the plan failed decisively. Write the headline of the retrospective in one sentence. (Example: "We hit 60% of revenue target because enterprise pipeline never materialized.")

## Step 2 — Generate failure modes (silently)
Each participant writes 5 distinct failure modes that could produce the year-end headline. Capture them in a shared doc. Target 30-50 total.

## Step 3 — Cluster and rank
Cluster failure modes into themes (market, team, execution, competitive, tech). For each theme:
1. Likelihood (1-5)
2. Severity (1-5)
3. Reversibility (1-5; 5 = reversible)

Rank by likelihood × severity × (6 - reversibility).

## Step 4 — Guardrails
For each of the top 5 failure modes:
- Leading indicator we can monitor
- Threshold that triggers a re-plan
- Owner
- Review cadence

## Step 5 — Plan amendments
What changes today based on the pre-mortem?
- New bets added
- Existing bets cut
- Bets with revised targets or milestones

## Output
1. Top 5 failure modes with guardrails
2. Amendments to the plan
3. The one failure mode the team was surprised they hadn't considered
Customize Variables0/3
Imagine the plan failed. List every reason. Fix the top three now.

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