Lenny's Podcast: Product | Growth | Career

A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals)

Mar 30, 2025

Ryan Singer, former Head of Strategy at 37signals and author of "Shape Up," shares his innovative approach to product development. He critiques traditional Agile methods for leading to endless cycles and introduces an appetite-driven strategy that sets fixed timelines. Singer emphasizes effective collaboration through shaping sessions and flexible team structures to clarify project goals. He highlights techniques like fat marker sketching to enhance communication and align engineering with design, making product development more efficient and empowering teams to thrive.

01:45:10

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Episode guests

Ryan Singer

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Episode notes

Podcast summary created with Snipd AI

Quick takeaways

The traditional Agile and Scrum methodologies often trap teams in endless cycles, hindering meaningful progress and timely product delivery.

An appetite-driven approach allows teams to set fixed timeboxes for projects, enabling flexibility in scope while committing to quality and timely outcomes.

Effective shaping sessions necessitate active collaboration among product managers, designers, and engineers to establish clarity and alignment on project goals.

Product managers should evolve from project overseers to strategic partners, focusing on defining problems and understanding market needs for successful product development.

Deep dives

The Importance of Shaping Sessions

Shaping sessions are critical in the product development process as they set the stage for what can realistically be accomplished within a given timeframe. By starting with a clear understanding of the end goal, teams can reverse engineer their approach to fit the time constraints they have. This method emphasizes the necessity of defining the maximum time they are willing to spend before beginning work rather than simply estimating how long a project will take. Such sessions encourage collaborative discourse among engineering, product, and design teams to clarify requirements and ensure a mutual understanding of the project’s objectives.

Intro

5min

Navigating 'Shape Up' in Product Development

7min

Shaping Innovation: The Basecamp Journey

12min

Optimizing Team Dynamics through Shaping Methodology

22min

Navigating Collaboration in Product Development

4min

Navigating Risks and Unknowns in Product Development

3min

Shaping Sessions in Product Development

16min

Bridging Product and Engineering: Navigating Challenges

29min

Navigating Product Development Challenges

3min

10.

Connecting and Collaborating: Insights on Product Development and Consulting

3min

Ryan Singer is one of the earliest employees and the former Head of Strategy at 37signals (the makers of Basecamp), where he spent nearly two decades refining a product development approach that helped the company build super-successful products with small teams. Based on these lessons, he wrote "Shape Up: Stop Running in Circles and Ship Work that Matters," and Ryan now works with companies of all sizes to them them escape the cycle of endless sprints, missed deadlines, and dragging projects.

What you’ll learn:

1. Why traditional Agile and Scrum methods often lead teams into endless cycles of work without meaningful shipping milestones.

2. The “appetite-driven” approach to product development where teams set fixed timeboxes (usually six weeks maximum) and vary the scope instead of expanding timelines.

3. The exact process for running effective “shaping” sessions that collaboratively define projects before committing resources.

4. Why most teams struggle with too little detail in their planning, not too much.

5. Why a 30-to-50-person team size is the critical breaking point when growing startups need to adopt more structured processes.

6. Practical techniques for bridging the engineering-design divide by bringing technical and product perspectives together earlier in the process.

7. The powerful “breadboarding” and “fat marker sketching” techniques that help teams align on solutions without getting lost in high-fidelity details.

8. The clear warning signs that your current development process is failing before it’s too late to change course.

9. Proven strategies to implement Shape Up methods, whether you’re working in a startup or enterprise environment.

10. A step-by-step approach to transitioning from Scrum to Shape Up by piloting the methodology with a single team before broader implementation.

11. Why the PM role shifts upstream in Shape Up, focusing more on problem definition than project management.

12. How to adapt Shape Up principles to your company’s unique context, even if it’s nothing like Basecamp.

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• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

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• Airtable ProductCentral—Launch to new heights with a unified system for product development

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Where to find Ryan Singer:

• X: https://x.com/rjs

• LinkedIn: https://www.linkedin.com/in/feltpresence/

• Website: https://www.ryansinger.co/

• Course: https://www.ryansinger.co/srl/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Ryan’s background

(04:38) The origins of Shape Up

(07:40) Implementing Shape Up in different companies

(09:56) How Shape Up is different

(19:02) The core elements of Shape Up

(26:29) Shaping sessions and timeboxing

(37:23) Flexible sprint planning

(38:56) The output of a shaping session

(46:57) Balancing detail and flexibility

(53:50) A deep dive into shaping sessions

(01:01:32) Fat marker sketches

(01:02:48) Getting started using Shape Up

(01:13:20) Signs it's time to try the Shape Up method

(01:18:25) Feature factories

(01:25:59) The role of the PM in Shape Up

(01:28:26) What makes Basecamp unique

(01:35:55) The second edition of the book

(01:38:30) Linking product strategy and shaping

(01:41:53) Conclusion and final thoughts

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Referenced:

• Basecamp: https://basecamp.com/

• David Heinemeier Hansson on LinkedIn: https://www.linkedin.com/in/david-heinemeier-hansson-374b18221/

• Jason Fried on LinkedIn: https://www.linkedin.com/in/jason-fried/

• Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking

• Des Traynor on LinkedIn: https://www.linkedin.com/in/destraynor/

• Intercom: https://www.intercom.com/

• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta

• How to find work you love | Bob Moesta (Jobs-to-be-Done co-creator, author of “Job Moves”): https://www.lennysnewsletter.com/p/how-to-find-work-you-love-bob-moesta

• Scrum: https://www.scrum.org/

• 37signals: https://37signals.com/

• Jobs to Be Done Theory: https://www.christenseninstitute.org/theory/jobs-to-be-done/

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Recommended books:

• Shape Up: Stop Running in Circles and Ship Work That Matters: https://basecamp.com/shapeup

• Demand-Side Sales 101: Stop Selling and Help Your Customers Make Progress: https://www.amazon.com/Demand-Side-Sales-101-Customers-Progress/dp/1544509987/

• Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612/

• Job Moves: 9 Steps for Making Progress in Your Career: https://www.amazon.com/Job-Moves-Making-Progress-Career/dp/0063283581

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

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Lenny's Podcast: Product | Growth | Career

A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals)

Episode guests

Podcast summary created with Snipd AI

Quick takeaways

Deep dives

The Importance of Shaping Sessions

Transition from Deadlines to Appetites

Collaboration Among Teams

The Role of the Product Manager

Emphasizing ShapeUp in Real Life

Pilot Projects as Testing Grounds

Challenges Beyond ShapeUp Implementation

Remember Everything You Learn from Podcasts