Ryan Singer

October 14, 2021

News: I'm giving a workshop on how to hand off and break down work

I'm interrupting the normal newsletter format to let you know about a workshop I'm giving. It's called The Confident Handoff. I'm giving it remotely to a small group of early adopters on November 22-23. Handoff is that point in time where the pitch goes to the build team to start the cycle. Why give a workshop about it? Whenever I ask ...
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August 17, 2021

17. Shape Up is for features, not all development work

I'm seeing a pattern among successful Shape Up teams. Companies first try Shape Up on a product team that builds features. They discover a new rhythm of shaping and shipping meaningful changes, and it feels like a victory. Then, they think "well since Shape Up is working ... we should try to do all development this way." But it turns o...
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August 3, 2021

16. "Done" is relative to what comes next

Right now I'm at the very beginning of a project with lots of unknowns. Starting it exposed me to a common pitfall where scope expands very early in the first steps of a project. I want to prototype a drag and drop interface to do this kick-off exercise. My plan of attack looks like the screenshot below. I sketched eight scopes at the ...
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July 29, 2021

15. Systemizing kick-off

Recently I tried a new exercise to systemize the way we kick off projects. Kick-off is that moment when the person who shaped the work hands it off to the development team. It's an important moment in Shape Up because the dev team takes full responsibility for interpreting the pitch, defining tasks, and coming up with the concrete solu...
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July 28, 2021

14. Small tools for shaping

I'm experimenting with ways to demonstrate the path from a raw idea to a well-shaped pitch. That is, how to go from "I think we should spend time on X" to "here's a specific concept for X that we're confident we can ship in six weeks." Sometimes I have a clear concept in my head from the very beginning, and I just need to sketch it out...
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June 14, 2021

13. Beyond to-dos

When work is turned into tickets, our brains shut off. In ticket-land, the work is a given, and it's just a matter of "doing it." This is true for any traditional to-do software. The thing is, when smart people tackle work, they actually do work on the work to figure out what the work is. They do it in their heads or on paper next to t...
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April 20, 2021

12. Matching problems to business imperatives

I keep getting questions about the work that happens before shaping a project. How do we decide if a problem is worth shaping? When does a problem deserve further research to frame the problem better? To answer this, our natural instinct is to weigh problems against each other. We ask “is this problem worse than that one?” or “which pr...
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April 13, 2021

11. Research gives us the problem, not the answer

I often get asked about how research fits into timeboxed work. If a team is working in a cycle and they can’t decide on a direction, should they do research? How do they fit that in a fixed timebox? This cuts to a fundamental question of where research belongs. If the team can’t decide which of multiple directions is better, it means t...
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April 12, 2021

10. Some solution vs. no solution

It’s natural to argue over what is the best, most perfect solution. Who would want to build anything less? This is especially true when we have our design or development hats on with a specific idea we hope to see in the final product. But it turns out that in the shaping phase, what’s “best” isn’t always the right question to ask. I’m...
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April 9, 2021

9. Shorthand for shaping

Here’s a look at some shorthand I’ve been playing with, early in the shaping process. I use this when I have a bunch of stuff in my head for a design but I don’t know where to start. I don’t know if all the pieces are going to combine or not. I don’t want to just start randomly and find out that I’ve painted myself in a corner, hit a d...
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