working-backwards▌
refoundai/lenny-skills · updated Apr 8, 2026
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Apply working backwards methodology to clarify product vision before building.
- ›Guides users through the core framework: identify the customer problem, write a mock press release, develop an FAQ, and evaluate three criteria (big idea, strategic fit, viable plan)
- ›Draws on insights from 12 product leaders including Ian McAllister, Bill Carr, and Melanie Perkins on starting with customer problems, defining ideal future states, and escaping incremental thinking
- ›Flags common mistakes like
Working Backwards
Help the user apply the working backwards methodology using frameworks and insights from 12 product leaders.
How to Help
When the user asks for help with working backwards:
- Start with the customer - Ask who the customer is and what problem they have, before discussing solutions
- Write the press release - Guide them through drafting a mock press release that describes the finished product
- Develop the FAQ - Help them anticipate and answer internal questions about feasibility and strategy fit
- Test the three criteria - Evaluate if the idea is big enough, strategically appropriate, and has a viable plan
Core Principles
Start with the customer problem
Ian McAllister: "Working backwards is all about the problem and starting there. Teams that do it wrong don't work backwards - they have something they want to build." Avoid retrofitting a problem to a pre-existing solution. Start with the problem paragraph before defining the solution.
Trust that results follow value
Bill Carr: "Jeff would say, we took it as an article of faith. If we served customers well, things like revenue and share price would follow." Work backward from the ideal customer solution and trust that business metrics will follow.
Use backcasting to escape the present
Christopher Lochhead: "Standing in that future, five years out, looking back to the present, what did we do to make this different future happen? That's how you unshackle yourself from the past." Envision a radical future and work backward without being constrained by current limitations.
The PR/FAQ forces clarity
Bill Carr: "We're going to start by writing a press release describing the feature in a way that speaks to the customer. The idea better jump off the page as something a customer will really need." Write a problem paragraph, a solution paragraph, a customer quote, and a leadership quote before building anything.
Evaluate three things
Ian McAllister: "One, is it a big idea? Two, is it something we should be doing? Three, is there a legitimate plan to succeed?" A successful product proposal must pass all three tests. The FAQ proves whether a legitimate plan exists.
Define the ideal state first
Melanie Perkins: "Column B is work from this dream reality and work backwards from how to achieve that." Imagine the 'castle on the hill' - the mythical perfect experience - first, then build rungs on a ladder from today to that vision.
Align the entire machinery
Anuj Rathi: "You're working backwards from an entire machinery at a particular day that is working. What will be the machinery we would have created so that this product is successful?" Working backwards includes GTM strategy, organizational alignment, and stakeholder buy-in, not just the product itself.
Define the theoretical ideal
Nilan Peiris: "What is the theoretical minimum cost for moving money? What is the theoretical maximum speed? Not just make it instant, make it cheap, but what actually is the lowest it could possibly be?" Define the best possible outcome and work backward from that, not from incremental improvements.
Questions to Help Users
- "Who is the customer, and what is their problem - in their words?"
- "If you wrote a press release for this product today, what would the headline be?"
- "What would a customer quote say about how this changed their life?"
- "Is this idea big enough to matter? Is your company the right one to build it?"
- "What's the FAQ that addresses the elephant in the room?"
- "What does the theoretical ideal state look like, not just an improvement?"
Common Mistakes to Flag
- Starting with the solution - The most common failure is having a solution and retrofitting a problem to it
- Vague customer benefit - The press release must jump off the page with clear customer value
- Skipping the FAQ - Internal questions about feasibility and strategy are crucial for honest evaluation
- Incremental thinking - Work backward from the ideal, not from small improvements to the status quo
- Only product focus - Working backwards should include GTM, organizational alignment, and stakeholder management
Deep Dive
For all 15 insights from 12 guests, see references/guest-insights.md
Related Skills
- Defining Product Vision
- Writing PRDs
- Startup Ideation
- Setting OKRs & Goals
How to use working-backwards on Cursor
AI-first code editor with Composer
Prerequisites
Before installing skills in Cursor, ensure your development environment meets these requirements:
- ›Cursor installed and configured on your development machine
- ›Node.js version 16.0+ with npm package manager (verify with
node --version) - ›Active project directory or workspace where you want to add working-backwards
Execute installation command
Execute the skills CLI command in your project's root directory to begin installation:
The skills CLI fetches working-backwards from GitHub repository refoundai/lenny-skills and configures it for Cursor.
Select Cursor when prompted
The CLI will show a list of available agents. Use arrow keys to navigate and space to select Cursor:
Verify installation
Confirm successful installation by checking the skill directory location:
Reload or restart Cursor to activate working-backwards. Access the skill through slash commands (e.g., /working-backwards) or your agent's skill management interface.
Security & Verification Notice
We perform automated surface-level scans (Gen AI Scanner, Socket, Snyk) during installation. These checks detect common vulnerabilities but do not guarantee complete security. Always review skill source code and verify the publisher's reputation before production use.
Skills execute code in your development environment. Always verify the publisher's identity, review recent commits, and test in isolated environments before production deployment.
List & Monetize Your Skill
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Use Cases▌
User Story & Requirements Generation
Create detailed user stories, acceptance criteria, and feature specs
Example
Generate user stories for 'password reset feature' with acceptance criteria, edge cases, and test scenarios
Reduce spec writing time by 50%, ensure comprehensive coverage
Competitive Analysis
Research competitors, compare features, identify gaps
Example
Analyze 5 competitor products, create feature comparison matrix, suggest differentiation opportunities
Complete competitive research in 2 hours instead of 2 days
Roadmap Prioritization
Evaluate features using frameworks (RICE, ICE, Kano) and create prioritized backlogs
Example
Score 20 feature ideas using RICE framework, generate prioritized roadmap with rationale
Make data-driven prioritization decisions faster
Stakeholder Communication
Draft PRDs, status updates, and stakeholder presentations
Example
Create executive summary of Q3 roadmap, monthly progress report, feature launch announcement
Save 3-5 hours/week on communication overhead
Implementation Guide▌
Prerequisites
- ›Claude Desktop or compatible AI client
- ›Access to product documentation and roadmap tools (Jira, Notion, etc.)
- ›Understanding of product management frameworks (RICE, Jobs-to-be-Done, etc.)
- ›Stakeholder contact information and communication channels
Time Estimate
30-60 minutes to see productivity improvements
Installation Steps
- 1.Install product management skill
- 2.Start with user story generation for known feature
- 3.Progress to competitive analysis: research 2-3 competitors
- 4.Use for roadmap prioritization: apply RICE/ICE scoring
- 5.Draft stakeholder communications and refine based on feedback
- 6.Build template library for recurring PM tasks
- 7.Share effective prompts with product team
Common Pitfalls
- ⚠Not validating competitive research—verify facts before sharing
- ⚠Accepting user stories without involving engineering team
- ⚠Over-relying on frameworks without qualitative judgment
- ⚠Not customizing outputs to company culture and communication style
- ⚠Skipping stakeholder validation of generated requirements
Best Practices▌
✓ Do
- +Validate research and competitive analysis with real data
- +Collaborate with engineering when generating technical requirements
- +Customize frameworks and templates to your company context
- +Use skill for first drafts, refine with stakeholder input
- +Document successful prompt patterns for PM tasks
- +Combine AI efficiency with human judgment and intuition
✗ Don't
- −Don't publish competitive analysis without fact-checking
- −Don't finalize user stories without engineering review
- −Don't make prioritization decisions solely on AI scoring
- −Don't skip customer validation of generated requirements
- −Don't ignore company-specific context and culture
💡 Pro Tips
- ★Provide context: company goals, constraints, customer feedback
- ★Ask for alternatives: 'Show 3 ways to prioritize this roadmap'
- ★Request stakeholder-specific formatting: 'Executive summary vs. engineering spec'
- ★Use skill for 70% generation + 30% customization to company needs
When to Use This▌
✓ Use When
Use for user story writing, competitive research, roadmap prioritization, stakeholder communication, and PRD drafting. Best for reducing repetitive documentation and research work.
✗ Avoid When
Avoid for strategic product vision (requires deep customer empathy), pricing decisions (needs market and financial expertise), or when face-to-face customer discovery is more valuable than speed.
Learning Path▌
- 1Basic: user stories, feature specs, status updates
- 2Intermediate: competitive analysis, prioritization frameworks, PRDs
- 3Advanced: product strategy, go-to-market planning, OKR setting
- 4Expert: product vision, market positioning, business model innovation
Discussion
Product Hunt–style comments (not star reviews)- No comments yet — start the thread.
Ratings
4.8★★★★★50 reviews- ★★★★★Xiao Singh· Dec 20, 2024
Useful defaults in working-backwards — fewer surprises than typical one-off scripts, and it plays nicely with `npx skills` flows.
- ★★★★★Michael Iyer· Dec 20, 2024
We added working-backwards from the explainx registry; install was straightforward and the SKILL.md answered most questions upfront.
- ★★★★★Maya Thompson· Dec 20, 2024
I recommend working-backwards for anyone iterating fast on agent tooling; clear intent and a small, reviewable surface area.
- ★★★★★Pratham Ware· Dec 16, 2024
Registry listing for working-backwards matched our evaluation — installs cleanly and behaves as described in the markdown.
- ★★★★★Min Martin· Dec 16, 2024
working-backwards fits our agent workflows well — practical, well scoped, and easy to wire into existing repos.
- ★★★★★Chaitanya Patil· Dec 12, 2024
working-backwards has been reliable in day-to-day use. Documentation quality is above average for community skills.
- ★★★★★Diego Bansal· Nov 11, 2024
I recommend working-backwards for anyone iterating fast on agent tooling; clear intent and a small, reviewable surface area.
- ★★★★★Aisha Haddad· Nov 11, 2024
Keeps context tight: working-backwards is the kind of skill you can hand to a new teammate without a long onboarding doc.
- ★★★★★Benjamin Gupta· Nov 11, 2024
Useful defaults in working-backwards — fewer surprises than typical one-off scripts, and it plays nicely with `npx skills` flows.
- ★★★★★Piyush G· Nov 3, 2024
Solid pick for teams standardizing on skills: working-backwards is focused, and the summary matches what you get after install.
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