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The Beautiful Mess Podcast

The Beautiful Mess Podcast

John Cutler 7 Episodes Dec 1, 2025

A podcast about how context and nuance impacts our work, how we collaborate, and how we organize. Hosted by John Cutler, author of The Beautiful Mess newsletter.

Episodes

TBM 392: When (And How) Tools Matter
TBM 392: When (And How) Tools Matter Dec 1, 2025 431 A video post!The Miro board used in the video can be accessed here:https://miro.com/app/board/uXjVJi6NCs8=/?share_link_id=616280785572(PS: Miro, I’d love another sweatshirt!)This framework explains why tools help in some situations and fail in others by grounding everything in the current state of a behavior. Every important behavior in an organization sits somewhere on a spectrum: it might be pur
TBM 365: The Problem With Value Hierarchies (Video)
TBM 365: The Problem With Value Hierarchies (Video) Jun 30, 2025 894 I’m experimenting with Substack’s Video feature. I’m not sure how this will look, appear, or even sound, but giving it a go. Below I include an outline of the video:Outline1. The Familiar Cascade* Many organizations use a hierarchical model: Pillars → Priorities → Initiatives → Epics → Tasks* Timeframes are often assigned at each level (e.g., 3–5 years at the top, sprints at the bottom)* Roles and
Product Coaching with Petra Wille
Product Coaching with Petra Wille May 26, 2024 2061 On this episode, I'm very honored to welcome Petra Wille. Petra is an experienced product leader, product leadership coach, and author. She has written two books, Strong Product People, A Complete Guide to Developing Great Product Managers, and Strong Product Communities.Community is something Petra is extremely passionate about and very good at. Petra, together with Arne Kittler, organize one of
20 Things I've Learned as a Systems (Over) Thinker (Extended Commentary)
20 Things I've Learned as a Systems (Over) Thinker (Extended Commentary) May 19, 2024 1054 Back in 2022, I wrote a post called 20 Things I've Learned as a Systems (Over) Thinker—”over” was in parentheses—and I've since received so much feedback about that post. I recently re-shared it on LinkedIn and it obviously strikes a chord. And so I thought that for this episode, I would just quickly go through that list, provide a little bit of extra color, and hopefully clarify some things.I'll
Sociotechnical Maestros with Gene Kim
Sociotechnical Maestros with Gene Kim May 12, 2024 1875 Today I'm talking to Gene Kim. Over the years Gene's work has had a huge influence on me. From books he authored and co-authored including The Unicorn Project, Phoenix Project, DevOps Handbook, and Accelerate, to his advocacy and community building with the DevOps Enterprise Summit, now called the Enterprise Technology Leadership Summit. I recently finished reading Gene's latest book Wiring the Wi
Software Development As Collective Learning With Hazel Weakly
Software Development As Collective Learning With Hazel Weakly Apr 28, 2024 1635 Back in late February, Tom Kerwin and I wrote a post titled How Capable Leaders Navigate Uncertainty and Ambiguity. The post listed 18 competencies—things like Accept We are Part of the Problem and Blend Diverse Perspectives—along with sample questions you could ask yourself, or someone else, to reflect on each competency.A couple days later, Hazel Weakly shared a deeply introspective post where s
Octopus Careers & Throwaway Stickies with Chris Butler
Octopus Careers & Throwaway Stickies with Chris Butler Apr 20, 2024 1788 Subscribe to The Beautiful Mess Podcast in your favorite podcast platform using this RSS URL: https://api.substack.com/feed/podcast/24711.rssIntroductionIn today's episode of The Beautiful Mess Podcast, I am talking to Chris Butler. Chris is currently a staff product operations manager at GitHub.During his career, he's worked at companies like Google, Facebook, Cognizant, Kayak, and Waze, as well

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