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We often assume that once we get everyone into a room for a collaborative modeling session, the hardest part is over. But what happens when you discover—just 48 hours before kickoff—that the person signing the checks has a fundamentally different definition of success than the product team?. In this episode, Beija Nigl joins Kenny and Andrew to share a candid story about a legacy migration project where the goalposts moved before the game even started. Beija recounts her experience facilitating a workshop intended to handle a 20-year-old legacy system where Java 8 support was running out. While the Product Owner wanted to completely "rethink" the broken processes, the sponsor introduced the session as a documentation exercise to rebuild the system's edge cases "as-is". This critical misalignment led to a room full of business experts getting bogged down in technical implementation details—debating status codes like "Status 800" and "nightly runs"—rather than solving the underlying business problems. This conversation goes deep into the socio-technical challenges of our work. We explore the emotional attachment stakeholders have to legacy complexity and how facilitators can navigate power dynamics when the "ground truth" is uncomfortable. Beija also reveals how this challenging experience became the catalyst for creating the "Como Prep Canvas," a tool designed to surface these conflicting motivations before the sticky notes ever hit the wall. Key Discussion Points [00:01] The Legacy Trap: Setting the stage for a workshop to replace a 20-year-old system facing end-of-life support. [03:00] The "Rebuild" vs. "Rethink" Conflict: Discovering at the 11th hour that the sponsor wants to document edge cases while the team wants to fix the process. [05:00] When Technical Debt Hijacks the Conversation: How the workshop drifted into mapping status codes (e.g., Status 800 vs. 305) instead of business value. [08:00] Emotional Safety in Modeling: Understanding why experts cling to complex legacy numbers as a form of job security and identity. [13:00] The Facilitator’s Dilemma: Navigating the tension of facilitation when you cannot refer to an aligned goal because one doesn't exist. [16:00] Delivering the "Ground Truth": The consultant's responsibility to present uncomfortable findings to leadership to drive organizational alignment. [19:00] Aligning on Intent: How to prepare mentally to ensure you are solving the right problem for the business success. Resources Mentioned Como Prep Canvas: The tool Beija developed with the DDD-crew to better align stakeholder expectations prior to collaborative modeling. https://github.com/ddd-crew/como-prep...