John Cutler, senior director of product management at Toast and writer of 'The Beautiful Mess' newsletter, discusses the complexities of collaboration and the need for deep alignment in product and design. He emphasizes the importance of listening to multiple frames and perspectives while exploring a way forward together. The podcast also explores the challenges of mapping an organization and suggests alternative metaphors for team dynamics in product development.
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John Cutler's Creative Roots
John Cutler started in a band named Blue, touring the U.S. for half a decade.
His love for messy creative endeavors led him to product management and writing "The Beautiful Mess" newsletter.
insights INSIGHT
Beware Simplistic Pattern Matching
Pattern matching in product development can fool us into oversimplifying complex realities.
Deep understanding requires seeing multiple frames and acknowledging diverse perspectives.
insights INSIGHT
Evolution of Product-Design Dynamics
Product and design relationships evolve unevenly across organizations.
Some companies still operate like it's 2003, others work with fluid, ad hoc collaboration today.
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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 https://rosenfeldmedia.com/events/
The Beautiful Mess, John Culter’s Substack https://cutlefish.substack.com/
Images of Organization by Gareth Morgan https://www.amazon.com/Images-Organization-Gareth-Morgan/dp/0761906320/
Rosenfeld Review Podcast 