Better Project Planning in 90 Minutes

Shape Up is the key manual for building software for the web. It offers a specific set of tactics that turn traditional planning on its head, greatly removes the agony from product definition, and ensures you ship on-time, every time.

I love “shaping” so much that David Calhoun and I ran an entire “Better Project Planning in 90 Minutes” workshop on it at the Dotcom Division Meetup in November 2023, and then an encore virtual workshop in December 2023. We presented these six concepts:

• Clarify the opportunity. Do not proceed to identifying the solution until everyone feels they fully understand the problem to be solved. Make sure the opportunity statement addresses these questions:
  • What is the problem or need to be solved?
  • Who experiences it, how frequently, and what’s their current workaround?
  • How does the competition solve it?
  • What makes it important, urgent, or valuable to solve right now?
• Appetites, not estimates. Estimates start with a design and end up with an (always incorrect) number. Appetites start with a number and end up with a design. Two key benefits include:
  • It creates space for the product team to cut scope along the way (as needed) in order to get something shipped.
  • It enables comparing potential projects apples to apples in the “betting” stage. If they have comparable cost (time), then the benefits can be more directly compared.
• Rough, bounded, and solved. Prepare the least amount of definition for your project. It will feel uncomfortable, but it will enable the product team to operate more effectively by applying their professional judgement while they work.
• Breadboards and fat marker sketches. Again, prepare the least amount of visual fidelity for the project plan. Designers often feel uncomfortable with this, but Jeff Golenski reports this “effectively reduced [the Automattic for Agencies] design iteration phases from ~3 down to 1”.
• Rabbit holes and no-gos. Fully explore the rabbit holes to identify the solution, and clearly identify what you aren’t doing as no-gos. The former increases your confidence in execution, and the latter makes stakeholder management much easier (“it’s ok that some things aren’t in scope”).
• Uphill slope and downhill slope. This is a useful communication tactic for identifying the current stage of the project. If you’re on the uphill slope, you’re still uncovering uncertainties. If you’re on the downhill slope, everything that’s remaining is known and you’re 90% confident in delivering the project on time, within scope, and meeting or exceeding expectations of quality. You should transition from the uphill slope to the downhill slope within the first two to three weeks of the project, otherwise it will likely blow past its appetite.

Importantly, you can take these as a “choose your own adventure.” Adopt them piecemeal based on whatever pain you’re experiencing, or simply use the language to influence your existing process.

Super grateful to the folks at Automattic for giving me a copy of the slides so I could share them with my new team at New_ Public.