Ryan Singer
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.
Engineering Skills
A high-performing engineering culture can be fostered by blurring the lines between design and implementation.
"Every designer codes. And I don’t just mean HTML. I mean, like running the app locally, going in to the place where that view is rendered to make that thing look the way that they want it to look... I..."
Leadership Skills
Empower teams by giving them a complete, shaped concept rather than a list of granular tickets.
"Instead, we want to have a whole idea, give it to a team so they see the whole, they really understand it, right? And then they can come up with their tasks and they can figure out how to track that a..."
Professional builders should be responsible for the 'how' of implementation once the 'what' is clearly defined.
"In the shape-up world, you have a single idea that was shaped... Go make your own tasks, because you’re the professionals... The contractors, if you’re building a house, they have to know the plans, b..."
Trade-off discussions are most productive when they happen 'upstream' during shaping, before resources are committed.
"Now, we can have a really cool conversation about trade-offs. So, let’s say we’ve got three different integrations here... If we just did this on one of those branches, would it be a win? And if we di..."
Effective shaping requires the simultaneous presence of product, design, and engineering expertise to resolve conflicts in real-time.
"You bring that person together with the product person who deeply understands the backstory... And then a designer in the room and they’re whiteboarding and wrestling with each other to get to what’s..."
Product Management Skills
Prioritization should be based on 'appetites' (how much time a problem is worth) rather than 'estimates' (how long a solution will take).
"What is our appetite for this? What is the maximum amount of time we’re willing to go before we actually finish something? And we have that startup moment... at least this, if not the whole project, t..."
Clarity on the final outcome is a prerequisite for starting any development work.
"The first thing is we are not going to start something unless we can see the end from the beginning. We’re not going to take a big concept and then say, 'What’s the estimate for this thing?'"
Effective problem definition involves 'framing' the issue to a specific, solvable pain point rather than a broad category.
"We narrowed it down to we understand that for our specific customers who are requesting this again and again, it’s more about I need to see empty spaces and in the existing agenda view, I can only see..."
The primary value of a Product Manager is in the 'upstream' work of defining the problem and business value before building starts.
"The PM moves upstream... less busy with, 'How do I get this project to not be in a bad state when it’s getting built?' And they’re way more in, 'How do I understand the business context? How do I narr..."
A well-shaped spec is a low-fidelity diagram that provides technical and functional clarity without over-specifying UI details.
"The output of the shaping session is... some kind of drawing or diagram where engineers, product, and design are all looking at that and they’re saying, 'We understand that. I know exactly what to go..."
Use low-fidelity tools like breadboarding to map out logic and flows quickly during collaborative sessions.
"In a shaping session, you can’t collaborate on something so high fidelity. So we need also some ways to collaborate... like breadboarding and fat marker sketching. These are tools to help us express a..."
Instead of estimating how long a feature will take, set a fixed time budget (appetite) and design a version of the solution that fits within it.
"We’re going to go the other way around and we’re going to say, what is the maximum amount of time we’re willing to go before we actually finish something? How do we come up with a idea that’s going to..."
Shaping is the creative process of adjusting a solution's complexity to match the available time budget.
"The second piece is this work that we call shaping and the shaping work is, how do we actually take this fixed amount of time that we’ve given for ourselves and vary the scope? How do we come up with..."
Use a 'circuit breaker' to stop projects that exceed their time box rather than allowing them to drag on indefinitely.
"If a project is not on track to actually finish after the six weeks, we’re just going to cancel it and rethink... we’re not going to keep reinvesting in something that we don’t understand. So, let’s t..."
Start with the fixed time constraint and work backward to define a scope that fits.
"What we found was that six weeks is the maximum that we can see into the future where we could actually say, 'How do we work backward and figure out something we could build in that six weeks and real..."