Thread

Painless Software Schedules (2000): Practitioner Discussion

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A practitioner thread arguing over estimates, phases, and why 'almost done' is unreliable. It is worth skimming to hear working engineers explain how schedules really slip, which sharpens how you read an agency's promises. Treat it as seasoned context, not gospel.

  • Experienced builders distrust vague completion percentages.
  • Small verifiable tasks are the only honest progress signal.
  • Estimates slip, so structure payments around what is shipped.
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The question it answers

  1. What's a fair way to structure a milestone-based contract with a dev agency?

Read with it

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  2. Basecamp's battle-tested, opinionated system for shipping meaningful work in fixed cycles without endless backlogs, a primary... Basecamp / 37signals Book · free online book Shape Up: Stop Running in Circles and Ship Work that Matters Ryan Singer
  3. Michael Seibel, who ran YC, makes the blunt case for shipping something almost embarrassingly simple and learning from real... Y Combinator Startup Library Video · ~10 min video How to Build an MVP Michael Seibel
  4. Once you have described a feature, acceptance criteria is how you say what done means so you and the developer agree before... Atlassian Article · 9 min read What is Acceptance Criteria? Definition, Examples, and Tips Atlassian
  5. A short, plain chapter that makes the case for keeping money and dates fixed while trimming features. It is the cleanest... 37signals Essay Getting Real: Fix Time and Budget, Flex Scope 37signals
  6. Spolsky shows why big vague tasks hide the truth and why breaking work into small pieces surfaces real progress. That is the... Joel on Software Essay Painless Software Schedules Joel Spolsky
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