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Learn to deliver ambitious engineering projects by combining RFC 2119's specification language with property-based testing techniques in this conference talk from StaffPlus New York 2025. Discover how to shift ambiguity left in project planning by creating clear, executable specifications that reduce risk in complex software development. Explore practical applications of Quickcheck-style property-based testing to generate comprehensive test suites from specifications, enabling safer collaboration with both human teams and AI systems. Gain insights from real-world experience with service meshes and distributed databases at companies like Uber and Microsoft, understanding how proper specification and testing practices can transform risky projects into successful deliveries. Master the connection between clear behavioral specifications and executable tests that help engineering teams confidently tackle otherwise daunting technical challenges.