(2025 Øredev) Leading Complexity: Modeling What the Moment Needs

Many of us working at the intersection of software, systems, and strategy are drawn to models - not just technical ones, but conceptual, organizational, and collaborative ones too. From Domain-Driven Design to Cynefin, from Event Storming to Team Topologies, we’ve built rich toolboxes to help us navigate complexity and coordinate action.

In complex environments, modeling isn't just a design tool — it can be a form of leadership. Drawing on system and conversational leadership, this talk explores how real leadership emerges in everyday moments: a well-placed question, a shift in framing, or a sketch that helps people see the system together. Whether you're in a design workshop or a town hall, as a formal leader, facilitator or participant, these small moves can shift the room.

We will explore modeling as a leadership practice when the “why and how” matters more than the “what". We will see how relational methodologies and conversational models can help us take the lead to move toward the change we want to see.

If you’ve ever left a meeting or workshop thinking, “we missed something important”, or "I didn't feel seen or heard", this talk might be for you. Whether you're a software engineer, facilitator, coach, or leader by title, this is an invitation to see modeling not just as a design tool, but as a way of leading that’s contextual, spontaneous, and rooted in the real moments where work actually happens.

Transcript

1. If you like — say hello to a neighbor — and share: What brought you to this session? “Leading Complexity - Modeling What the Moment Needs” The Unofficial Start 👋
2. Leading Complexity - Modeling What the Moment Needs Xin Yao, Øredev 2025
3. Hi, I am Xin 👋
4. Leadership Complexity Modeling Conversa- tion Collabo- ration
5. Complexity Leadership In this session we will explore —
6. In your groups of three: What caught your attention in this framing? Share the sparks - curiosity, surprise, contradiction, resistance … Complexity Leadership (Let’s reflect on a framing) Aha 💡 Love it 🤩 Hmm… 🤔 Yes, but ❓ Complexity Leadership = Inspiration: Patricia Shaw, Joe Hudson to follow what matters where outcomes are uncertain capacity for taking the lead →
7. #Complexity leadership #Conversation modeling
8. 👉 Points to ponder • A capacity, not a title or role. • To lead is to follow (a conviction). • Conviction is not hard-headedness. • Possibility, not causality • No responsibility for outcomes Complexity Leadership = Complexity Leadership (A framing) Inspiration: Patricia Shaw, Joe Hudson to follow what matters where outcomes are uncertain capacity for taking the lead →
9. [Gallup Report 2024] Global Employee Engagement Status Boxed numbers indicate %-point change from the year before
10. Modeling contexts Work Modeling Collaboration Modeling Modeling what we build — software, product, or strategy. Modeling how we align and coordinate — using structured techniques to reach target outcomes. Modeling open-ended conversations for connection & possibilities — using relational methodologies. MATURE MATURING EMERGING Work→ Collaboration → Conversation Conversation Modeling
11. 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.
12. Leader as convener
13. My worst event storming workshop
14. Workshop Retrospective
15. What is it about this situation that is making an open exchange di cult? What is the future we dream of for this domain? What are you most passionate about contributing to in this domain? The questions that got us unstuck
16. # model questions # model attention
17. Possibility conversation The Ownership conversation The conversation The Gifts Commitment conversation The conversation The Dissent Invitation conversation The the Six Conversations Conversational Leadership Credit: Peter Block
18. Possibility conversation The Ownership conversation The conversation The Gifts Commitment conversation The conversation The Dissent Invitation conversation The the Six Conversations Inversions when leading complexity Credit: Peter Block Problem → Possibility Deficiencies → Gifts Entitlement → Ownership Obligation → Choice Lip Service → Dissent Compliance →Promise
19. conversation The Dissent the Six Conversations Credit: Peter Block The leadership task … is to surface doubts and dissent without having an answer to every question. • What are your doubts or concerns? • What is not getting airtime — but perhaps should? • What would you say if you didn’t need to be polite? If you can’t say no, your yes has no meaning. ~Peter Block The Dissent Conversation [Lip Service → Dissent]
20. Possibility conversation The the Six Conversations The Possibility Conversation Credit: Peter Block The leadership task … is to shift from problem solver to possibility thinker. Open space for imagining & declaring a different future. • What are you aiming to achieve and what about that is important? (reframing “expectations”) • What if ____? (reframing problem definition) Possibility is not a goal or prediction, it’s not optimism. ~Peter Block [Problem → Possibility]
21. Invitation conversation The the Six Conversations Credit: Peter Block The leadership task … is to name the debate, issue the invitation, and engage those who choose to show up. Powerful Invitation • Declare the possibility • Offers choice - ok to say no • Name the hurdle - what’s required of people if they choose to show up. Real accountability only occurs through choice. ~Peter Block The Invitation Conversation [Obligation → Choice]
22. [Dissent] What is it about this situation that is making an open exchange di cult? [Possibility] What is the future we dream of for this domain? [Possibility] What are you most passionate about contributing to in this domain? The questions that got us unstuck
23. [Invitation] Q: What made you choose to continue the DDD workshops? [Invitation] A: You were trying to convince us before. Now we are testing ideas together. [Name the Hurdle] If you accept the invitations to continue, something will be required of you. [Possibility] What if we ____? What else is possible?
24. Leader as connector
25. The undiscussables - calling them out? Guilt Doubt Blame Resentmen t Fear
26. [Scenario] The Pre-decided Outcome A domain modeling workshop was framed as “collaborative,” but it became clear early on that POs and architects had already made key decisions. You noticed people disengaging, and tension building up in the room. In-the-moment Weren’t we supposed to model together? Should I call it out? But, why me? Can’t you see you are disempowering people? Story in my head “I’m sensing a bit of tension or confusion — would it make sense to revisit the assumptions behind those boundary decisions?” “Could we maybe double-click on those boundaries you just shared? It’d help me contribute better if we can clarify what’s still open for discussion. ” Call it out Fear Frustratio n Blame
27. [Follow what the moment needs] Make the Undiscussable discussable Prompts for naming the undiscussable • “Can we pause for a moment - I feel we need a bit more clarity before moving on.” • “I sense a bit of tension in what was just said — should we check in on that?” • “I feel like we might be skipping over something important — can I speak my mind?” • “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. Ownership conversation The the Six Conversations Credit: Peter Block The leadership task … is to confront people with their freedom, in a space of connection and belonging • What am I doing — or not doing — that keeps this problem in place? • What conversations have I avoided that could shift something important? • How might I become the cause, not the effect? Blame, entitlement & waiting for someone else to change is a defense against ownership. ~Peter Block The Ownership Conversation [Blame / Entitlement → Ownership]
29. Commitment conversation The the Six Conversations Credit: Peter Block The leadership task … is to ask for authentic commitment to how we show up, not to a plan • What promise am I willing to make about how I show up in the world? • What risks am I willing to take for the success of the whole effort? • What’s the promise I am not willing to make, yet? To be committed means you are willing to make a promise with no expectation in return. ~Peter Block The Commitment Conversation [Compliance → Promise]
30. conversation The Gifts the Six Conversations Credit: Peter Block The leadership task … is to bring the gifts of people from the margin into the center. Gifts questions are accountability questions. • What quality of yours is under-used in your daily work? • What is a gift of yours no one knows about? • What positive feedback still surprises you? • What gift have you received from this room today? What do you want from me? My deficiencies or my capacities? ~Peter Block The Gifts Conversation [Deficiencies → Gifts]
32. #Polarities & Paradoxes #Sociotechnical architecture
33. Leading Complexity Steer the boat AND Influence the river Follow the current AND
34. Plan Emergence # model work # model collaboration # model conversation # model attention Systems Thinking Systems Being
35. Quality attributes in sociotechnical architecture Connectedness Aliveness Belonging Freedom Wholeness Modularity Scalability Security Elasticity Reliability Social Architecture Technical Architecture Openness Usability
36. [Sociotechnical architecture] Connect the people, split the software Connectedness Aliveness Belonging Freedom Wholeness Modularity Scalability Security Elasticity Reliability Social Architecture Technical Architecture Openness Usability
37. • What’s one gift or insight you choose to take away from this session? • What courage will it take to put that gift to use in your everyday work? A final reflection …
38. Thank you! Leading Complexity - Modeling What the Moment Needs Xin Yao @settling-mud.bsky.social @xinyao@mathstodon.xyz https://www.linkedin.com/in/xinxin