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Explore a case study on transforming legacy software in this conference talk from LeadDev New York 2024. Discover strategies for overcoming challenges in digital transformation, including technical debt, emotional attachment to code, and skepticism. Learn how to navigate complex emotions and cognitive friction within multi-disciplinary teams working on innovative solutions. Gain insights into breaking through impasses caused by professional identity threats and emotional dominance. Uncover effective tools and strategies for understanding and addressing complex emotions, identifying biases, and successfully completing software transformations. Benefit from real-world experiences and practical advice on pulling teams out of trenches to achieve successful digital transformation outcomes.