- Speakers
John Cutler and Xin Yao
- Date
- Description
In the world of modern software design, we are confronted with multidimensional complexity—an entangled interplay between business needs, organizational constraints, and technical intricacies. We tend to see this complexity as a problem to be solved, rather than a beautiful mess to be navigated and draw deep learning from.
Jacob Needleman once remarked: “Our culture has generally tended to solve its problems without experiencing its questions.” Can we practice modeling and design in a way, so it is less about defining a target architecture or making a decision, and more about fostering spaces for deep inquiries about the why, the what, the for whom, and the with whom? Sociotechnical paradoxes - stability vs. emergence, order vs. chaos, and getting stuck to get unstuck - are not contradictions to be eliminated but opportunities to be engaged with.
In this talk, we delve into how collaborative working sessions, enriched with meaningful inquiry, storytelling and sense making, can become part of our modeling and design toolbox. They might get us closer toward both social and technical coherence through lived experiences of parts connecting with the whole. We explore how to practice inquiry-driven architecture to catalyze shared understanding and aspirations, build rich relations while profiting from diversity, uncertainty and ambiguity.
To co-create innovative products and sophisticated software, we must compose it like a dynamic music performance — balancing the clarity of written notes with the raw, transformative power of our collective listening and improvisations. Success depends on blending clear, disciplined plans with the creative energy of real-time collaboration. Only by embracing uncertainty, pain, and the beauty of our messy, shared reality can we unleash our collective imagination, co-create products and software that can brave our time’s unique challenges.
About John Cutler
John Cutler focuses on the messy overlaps and patterns of product—The Beautiful Mess (the title of his newsletter). He is currently Head of Product at Dotwork, a platform for instrumenting your product operating system. 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,and Medium.
About Xin Yao
Xin is an independent consultant specialized in Domain-Driven Design (DDD), architecture modernization, sociotechnical complexity and systems thinking. She frequently speaks at international design and architecture conferences. In her earlier career, Xin has been chief architect in Danske Bank, spearheading large-scale initiatives. An experienced architect and an avid change practitioner, Xin nudges organizations at crossroads to move beyond seeing architecture as an upfront design blueprint. She is deeply committed to collective reasoning and participatory discovery. Xin facilitates languaging, modeling and reflective conversations to help teams and organizations make sense, make decisions, split software, and connect with each other.