The REWORK Podcast

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 help 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. — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny • Merge—A single API to add hundreds of integrations into your app: http://merge.dev/lenny • Airtable ProductCentral—Launch to new heights with a unified system for product development: https://www.airtable.com/lenny Find the transcript at: https://www.lennysnewsletter.com/p/shape-up-ryan-singer 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/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ 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 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/ ...References continued at: https://www.lennysnewsletter.com/p/shape-up-ryan-singer 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 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.

600+ episodes to help you launch and grow your startup Whether you’ve launched your startup or you're just thinking about it, learn from successful founders who have been in your shoes. Subscribe & Review: iTunes: https://podcasts.apple.com/us/podcast/startups-for-the-rest-of-us/id366931951 Spotify: https://open.spotify.com/show/2Ww2e4JNO2cfxWC2ImR7DJ Stitcher: https://www.stitcher.com/podcast/startups-for-the-rest-of-us

Become an Epic Product Engineer is Kent C. Dodds's interview podcast about skills that stay valuable as AI takes on more implementation. It's all about product engineering. Blending technical depth with product judgment, user empathy, and problem clarity. Each episode is a long-form conversation with a guest who has shipped real software and cares about building the right thing before making it right. You get full audio, transcripts, structured show notes, homework (one concrete action to try), and links from the conversation. Canonical home for the show and every episode page: https://www.epicproduct.engineer/become-an-epic-product-engineer-podcast New episodes publish on Wednesdays. Complements Better with Kent — Kent's solo series on durable skills for people who ship software.

Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product

A step-by-step breakdown of a real project done Shape Up style. 00:00 - Framing/Shaping terminology and assumptions 02:47 - What is Shape Up 03:38 - Basecamp vs. more typical real-world teams Case study: 04:49 - Simple kanban for framing/shaping checkpoints 05:11 - A candidate from top leadership with unanswered questions 06:55 - Framing the problem/outcome with an SME 10:34 - Why I need to shape before jumping forward 11:35 - Shaping session with a senior engineer 15:29 - Back to framing with the SME 17:42 - Shaping session with the senior engineer and SME 19:19 - Writing it up for kickoff 20:57 - Kickoff with the team 21:30 - Mapping out vertical slices (scopes) 23:54 - Wiring first, high fidelity last 25:17 - The launch brief 26:01 - Reflection: Roles involved, progressively getting warmer 26:28 - Reflection: Long stretches of autonomy and spiky live sessions 27:53 - Misunderstanding about pitches. Shaping one thing per time box. 29:12 - Shaping in Real Life Series Visit http://ryansinger.co for more.

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