(2026 OOP Keynote) Modeling Conversations in Complex Collaboration - Unfolding Everyone's Best

Complex software work demands complex collaboration. Over the last decade, Collaborative Modeling (CoMo) techniques such as EventStorming, design studios, and ADR workshops have significantly improved how we design together. Yet a crucial gap remains. We have strong guidance on structures, steps, and artefacts — but very little on how to design the conversations that hold collaboration together under complexity.
In practice, teams still rely on habitual ways of talking. Dissent remains unspoken, ownership stays unclear, and “undiscussables” end up shaping decisions. Because how we talk shapes what we build, our systems inevitably carry traces of these conversational patterns.
This keynote introduces conversation modeling as the next frontier of Collaborative Modeling. Drawing inspiration from Peter Block’s Six Conversations, Christopher Alexander’s notion of unfolding, and Humberto Maturana’s experiential coherence, we frame conversational design as a sociotechnical practice.
The session includes a couple of small, interactive elements — designed for reflection and experimentation, not performance. You’ll be invited to notice your own everyday conversational leadership capacity. Together we will reflect on how intentional dialogue can support better collaboration, better decisions, and create the conditions for unfolding everyone’s best.

Transcript

1. Modeling Conversations in Complex Collaboration Xin Yao, OOP 2026, Keynote Unfolding Everyone’s Best
2. Hi, I am Xin 👋
3. software product strategy Conversa- tion Collabo- ration
4. Use conversations to amplify collaboration bandwidth
6. Connection Before Content
7. A chat with the person next to you: What’s coming up on your calendar? • What’s one conversation you hope will happen? • Or, which one are you worried might not get airtime? Connection Before Content 👋
8. Why do conversations matter?
9. [Gallup Report 2025] Global Employee Engagement Status Boxed numbers indicate %-point change from the year before
10. We are in a global epidemic of isolation and loneliness
11. What’s hard in high-stakes, high-intensity collaboration?
12. We are all blind scholars. We all hold a meaningful part of the truth. We need each other to see a picture of the whole.
13. How do we have productive conversations across insurmountable differences?
14. Conversation amplifies collaboration Unfolding, connecting, emerging, complexifying (parts → whole) Co-creation Contribution Connection Effective Empowered Engaged ME WE
15. What conversations are impactful?
16. Some conversations can turn a group into a community Group Team “We happen to be in the same room.” “We need to get this done.” “This matters to us.” A collection of people Community Roles, Goals, Delivery Connection, Belonging, Care
17. The Six Conversations hold the possibility to transform a group of people into a community of contributors and co-creators. Peter Block “”
18. Possibility conversation The Ownership conversation The conversation The Gifts Commitment conversation The conversation The Dissent Invitation conversation The the Six Conversations Credit: Peter Block
19. Possibility conversation The Ownership conversation The conversation The Gifts Commitment conversation The conversation The Dissent Invitation conversation The the Six Conversations Inversion of conversational habits Credit: Peter Block Problem → Possibility Deficiencies → Gifts Entitlement → Ownership Obligation → Choice Lip Service → Dissent Compliance →Promise
20. The moment we have answers, there is no dialogue. Questions unite people. Elie Wiesel “”
21. Better answers Better questions
22. Our culture has generally tended to solve its problems without experiencing its questions. Jacob Needleman “”
24. Alignment looks neat, coherence looks alive “Conversational centers that unfold everyone’s best” Credit: Christopher Alexander, Humberto Maturana
25. So what can I actually do?
26. The undiscussables - calling them out?
27. [Make the undiscussable discussable] Low-risk interruption phrases Call out the undiscussable without blame • “Can we pause for a moment - I feel we need a bit more clarity before moving on.” • “I sense a bit of tension — should we check in on that?” • “I feel like we might be skipping over something important - can I ask a question?” • “Can we double-click on that? A bit more clarity would help me contribute better.” • “I’m sensing some discomfort and not sure how to say it — can I share what’s on my mind?” • “I wonder if we could stay with that edge case a bit longer - it’s going a bit fast for me.” • “Could we hear from someone we haven’t heard yet?” 🗣Use these as mini-intervention templates, adapt to the situation.
28. State matters more than script Judgment Blame Resentment Fear
29. VIEW - a model for “personal state management” Credit: Joe Hudson
30. Have VIEW conversations, stay connected Credit: Joe Hudson
31. One of the ways of thinking about leadership is thinking about convening conversations that might not happen otherwise. Patricia Shaw “” … and having the courage to do that.
32. Key Points • Conversation amplifies collaboration • Conversation unfolds Connection, Contribution, and Co-creation • The Six Conversations help turn a group into a community • Model conversations with powerful questions • We all have conversational leadership capacity • Make the undiscussable discussable • Have VIEW conversations. • State matters more than script Picture Credit: Jacqui Read
33. Modeling Conversations in Complex Collaboration Unfolding Everyone’s Best Xin Yao @settling-mud.bsky.social @xinyao@mathstodon.xyz https://www.linkedin.com/in/xinxin Thank you!