home / skills / coowoolf / insighthunt-skills / divergent-working-backwards

divergent-working-backwards skill

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/strategy-planning/divergent-working-backwards

This skill helps teams explore three divergent product strategies by drafting full PR/FAQs and comparing trade-offs before committing.

npx playbooks add skill coowoolf/insighthunt-skills --skill divergent-working-backwards

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---
name: divergent-working-backwards
description: Use when defining new product lines or major pivots, when single PR/FAQ leads to tunnel vision, or when giving leadership real strategic choices instead of yes/no decisions
---

# Divergent Working Backwards (3 PR/FAQs)

## Overview

An enhancement of Amazon's "Working Backwards" process. Instead of writing one Press Release, the team writes **three distinct, divergent PRs** to explore different strategic directions before converging.

**Core principle:** Power of Three—always explore three radically different solutions.

## The Process

```
┌─────────────────────────────────────────────────────────────────┐
│  1. DEFINE THE CUSTOMER PROBLEM                                 │
│     What are we solving?                                        │
├─────────────────────────────────────────────────────────────────┤
│  2. IDEATE 3 DIVERGENT SOLUTIONS                                │
│     NOT variations—strategic alternatives                       │
│     Example: Tiered vs. Points-based vs. Segment-focused        │
├─────────────────────────────────────────────────────────────────┤
│  3. DRAFT 3 DISTINCT PR/FAQs                                    │
│     Full press release for each future                          │
│     Include compliance, legal, ops details                      │
├─────────────────────────────────────────────────────────────────┤
│  4. STAKEHOLDER REVIEW & DEBATE                                 │
│     Compare the 3 futures                                       │
│     Force real trade-off discussions                            │
├─────────────────────────────────────────────────────────────────┤
│  5. SELECT ONE PATH & COMMIT                                    │
│     Disagree and commit once chosen                             │
└─────────────────────────────────────────────────────────────────┘
```

## Key Principles

| Principle | Description |
|-----------|-------------|
| **Divergence first** | Prevents falling in love with first idea |
| **Show don't tell** | Write full PR/FAQ, not just bullet points |
| **Leadership choice** | Give real options, not yes/no on single plan |
| **Commit after debate** | Once chosen, full commitment |

## Common Mistakes

- Writing three variations that are only slightly different
- Not pushing to truly divergent strategic alternatives
- Skipping the full PR/FAQ detail for each option

---

*Source: Anuj Rathi (Jupiter Money, Swiggy) via Lenny's Podcast*

Overview

This skill adapts Amazon’s Working Backwards into a structured exercise that produces three fully realized, divergent Press Releases and FAQs. It forces teams to explore radically different strategic futures instead of iterating on a single concept. The outcome is clearer trade-offs for leadership and a stronger basis for committing to one direction.

How this skill works

Start by defining the core customer problem you intend to solve. Then ideate three genuinely different strategic approaches and write a complete PR/FAQ for each, including compliance, operations, and legal considerations. Use stakeholder review to debate the trade-offs, then select one path and commit to execution.

When to use it

Defining a new product line or major market pivot
When a single PR/FAQ causes tunnel vision in the team
Before presenting options to leadership to avoid yes/no choices
When you need to validate fundamentally different monetization or segmentation strategies
During strategic offsites or product kickoff workshops

Best practices

Insist on three truly divergent strategies, not incremental variations
Write full PR/FAQs that describe customer experience, metrics, and risks
Include cross-functional reviewers early—legal, ops, finance
Use the review to expose trade-offs, not to merge ideas prematurely
After selection, adopt a ‘disagree and commit’ stance and allocate resources

Example use cases

Choosing between tiered pricing, points-based rewards, or segment-specific offerings
Deciding whether to build a new product, acquire a partner, or license technology
Repositioning a product for different customer segments (enterprise vs SMB vs consumers)
Evaluating three go-to-market strategies for international expansion
Preparing leadership with clear, comparable strategic choices instead of a single recommendation

FAQ

Why three options and not two or four?

Three encourages contrast without overwhelming decision-makers—two can be binary and limiting, more than three diffuses focus.

How different should the PR/FAQs be?

They should be strategic alternatives that would lead to different roadmaps, cost structures, and customer outcomes—not minor feature variants.