Guest: Ryan Singer, Former Head of Product Strategy at Basecamp, creator of Shape Up
Key Insights
Reverse Engineering Success: Product teams can ship faster by setting a fixed time (e.g., six weeks) and shaping a solution to fit, rather than estimating open-ended tasks.
Collaborative Clarity: Bringing engineers, designers, and product managers together early in shaping sessions prevents costly misunderstandings later.
Appetite Over Estimates: Defining how much time a business is willing to invest forces sharper trade-offs and avoids scope creep.
Practical Adaptation: Shape Up works beyond Basecamp’s unique setup, but requires tailoring to real-world team dynamics and pressures.
1. Renovating Product Development: The Shape Up Philosophy
Ryan Singer introduces Shape Up, a method born at Basecamp to streamline product development by flipping traditional approaches. Instead of sprawling estimates, teams define a time "appetite" and craft solutions to fit within it.
Singer uses a home renovation analogy: “You can have a beautiful rendering of the new bedroom with lamps on the side of the bed coming out from the wall. But if you haven’t checked if there’s electricity in that wall, it’s going to drastically change the cost and time”. This underscores the need to verify feasibility upfront.
Shape Up starts with a "shaping session" where cross-functional teams align on a clear, actionable idea, avoiding vague goals like “build a calendar.”
The method prioritizes finishing over perfection, aiming to ship meaningful increments in fixed cycles, typically six weeks or less.
2. From Chaos to Clarity: How Shaping Sessions Work
Shaping sessions are the backbone of Shape Up, blending creativity and pragmatism to define projects. Singer details their mechanics and impact.
Structure: Sessions last about three hours, often spanning multiple meetings, involving a senior engineer, designer, and product manager. “We come out with some kind of drawing or diagram where engineers, product, and design are all looking at that and saying, ‘We understand that’”.
Output: A concrete plan—like a two-month dot grid calendar with a scrolling agenda—emerges, detailed enough to build but not overly polished (e.g., no Figma files yet).
Benefit: Early collaboration catches risks, like hidden code complexity, before resources are committed, saving time and morale.
3. Appetite as a Superpower: Timeboxing with Purpose
Singer champions "appetite" over estimates, a shift that forces discipline and focus.
Definition: Teams decide the maximum time worth spending—say, two or six weeks—then shape a solution to fit. “What is the maximum amount of time we’re willing to go before we actually finish something?”.
Real-World Twist: If a project overshoots, it’s pulled back to shaping, not extended blindly. “We’re not going to keep reinvesting in something we don’t understand”.
Impact: This avoids the common trap where a “two-week landing page” balloons to six, keeping teams accountable to business priorities.
4. Basecamp’s Bubble: Adapting Shape Up to Reality
Shape Up thrived at Basecamp, but Singer warns it’s not plug-and-play for every company.
Basecamp’s Edge: Designers code, founders steer directly, and there’s no sales team vying for engineering time. “Imagine you have no sales org… no such thing as a request from sales”.
Real-World Fix: Outside Basecamp, shaping requires bridging silos. Singer learned this post-exit: “It took me a while to realize there’s no engineer in the picture here”.
Advice: Start with a pilot project, aligning product and engineering leaders to pick a meaningful, manageable goal—like a three-week feature—and shape it together.
5. When to Jump: Signs Shape Up Could Save Your Team
Singer pinpoints when Shape Up becomes a lifeline for struggling teams.
Early Warning: At 30-50 people, when founders delegate and speed stalls. “We thought we put everybody in the right roles… and everything is just grinding”.
Late Crisis: In entrenched orgs where “nothing is getting out the door” despite years of process. Symptoms: Projects drag endlessly, clarity fades, and execs demand movement. “We can’t keep ending where we still can’t see the end of it”.