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The Beautiful Mess of Product Development with John Cutler

Today’s interview is just a taste of what you’ll learn at Rosenfeld’s upcoming Design in Product conference—featuring John Cutler’s closing keynote. John is the senior director of product management at Toast, a doodler, a former band member, a UX researcher, and business analyst. He’s also the prolific writer behind “The Beautiful Mess, a Substack newsletter with over 36,000 subscribers, where he writes about cross-functional product management—especially the messy parts. 

As someone who likes “messy, creative endeavors” and building things with other people,  John enjoys unpacking the complicated parts of collaboration, getting to the heart of messes, and finding a way forward involves much more than identifying patterns. 

John finds that each person’s frame or perspective is only one of many. This is one reason the relationship between product and design is a complicated ecosystem, and the whole system—not just a part—needs to evolve together.    

In an effort to reach consensus across teams, John notes that it’s easy to fall into the alignment trap where the so-called alignment is fragile and where consensus becomes more valued than a true solution.  John encourages listeners to get comfortable with the complicated mess, to truly listen to multiple frames and perspectives while holding onto their own, and then to roll up their sleeves and explore a way forward together. 


What you’ll learn from this episode:

  • About John’s background and his brief stint in a band that opened for others
  • About the upcoming Design in Product conference
  • About the messiness of product development and problem-solving
  • About avoiding the traps of alignment and over-simplification


Quick Reference Guide

[0:00:24] Introduction of John Cutler and Design in Product 2023, and the back story behind “The Beautiful Mess”

[0:05:01] Patterns in messes

[0:10:23] The relationship between product and design

[0:14:11] Dealing with varying work speeds and perspectives 

[0:20:32] Design Ops Summit, October 2-6, 2023

[0:21:45] The alignment trap and the simplification trap

[0:30:50] A new metaphor for looking at teams in organizations

[0:34:04] John’s special words for listeners


Resources and links from today’s episode:

Design in Product 2023 

The Beautiful Mess, John Culter’s Substack

Images of Organization by Gareth Morgan