Is your roadmap a beautiful mess? - John Cutler

In episode 46 of "Talking Roadmaps," Phil Hornby interviews John Cutler on the intricacies of product roadmapping. They explore the challenges of balancing structure with flexibility, the impact of company culture on roadmap success, and tips for maintaining alignment across teams. John shares insights from his diverse experience in product management, emphasizing the importance of embracing the 'beautiful mess' of product development.

John Cutler focuses on the messy overlaps and patterns of product—The Beautiful Mess (the title of his newsletter). Until recently, John supported product teams at Toast as Senior Director, Product Enablement. Prior to Toast, he was a product evangelist and coach at Amplitude where he interacted with diverse product teams and product leaders from around the world. There are few people in the world that have this kind of exposure, and if you follow John's writing over the last couple years I'm sure you can see the influence of this perspective. He has a background in product management and UX research, including B2B SaaS companies like Zendesk, Pendo, and AppFolio, and before that B2C, ad-tech, banking, and media. John is a prolific (or some might say obsessive) writer, with almost a thousand posts spread across various newsletters, blogs, Substack and Medium.

Timestamps
00:00 - Introduction
01:12 - What is the job to be done of a roadmap?
03:14 - Who is the typle audience of a roadmap?
09:55 - How do vision, strategy, objectives etc. link into the roadmap?
26:20 - What is a roadmap made of?
38:04 - What would you consider best practice when it comes to roadmapping?
45:47 - If you had to distill your philosophy of roadmapping be in just 1 or 2 sentences, what would it be?
45:54 - Is there anything about roadmapping that hasn't been asked?
52:39 - How do you help people and how can they get in touch?

Thanks for watching 👍

Be sure to check out John's links...
LinkedIn:   / johnpcutler  
Substack: https://cutlefish.substack.com/
Medium:   / johnpcutler  
Book mentioned: Collaborating with the Enemy - https://www.amazon.com/Collaborating-...
11 Ways I Visualized Product Development Work: https://cutle.fish/blog/11-ways-i-vis...
Frames: https://cutlefish.substack.com/p/tbm-...
Mandate Levels: https://cutlefish.substack.com/p/tbm-...
Garbage Can Theory: https://en.wikipedia.org/wiki/Garbage...

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Phil Hornby and Justin Woods, Co-hosts and Co-creators of Talking Roadmaps
https://www.talkingroadmaps.com/

#roadmaps #expert #practitioner