When Windows Hit The Wall: Reinventing a Dominant Product in a Changing Market with Steven Sinofsky I Postman

In this episode of Breaking Changes, Postman Head of Product-Observability Jean Yang interviews Steven Sinofsky, former Microsoft executive, diving into his journey in engineering leadership and the hurdles faced during the Windows 8 rewrite. Gain valuable insights on team dynamics, the essence of shipping software collectively, and Microsoft's adaptability in the ever-evolving tech landscape.

For more on Steven Sinofsky, check out the following:

LinkedIn: https://www.linkedin.com/in/sinofsky/

Twitter: https://twitter.com/stevesi

Personal Website: https://medium.learningbyshipping.com/

Company Website: https://a16z.com/

Follow Jean on Twitter/X @jeanqasaur. And remember, never miss an episode by subscribing to the Breaking Changes Podcast on your favorite streaming platform or Postman's YouTube Channel—just hit that bell for notifications.

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Episode Timestamps

00:00 - Introduction and Background 03:12 - Getting into Engineering Leadership 11:29 - Windows 8 Rewrite and Challenges 24:46 - Team Formation and Building 42:43 - Adaptability of Microsoft 43:43 - Resistance to Software as a Service 44:58 - Product Market Fit and Innovation 46:22 - The Importance of Product Market Fit 47:32 - Underrated Breaking Changes in the Industry 50:02 - Breaking Changes Introduced by AI 52:26 - Exciting Changes in the Next Year 53:39 - Where to Find Steven Sinofsky