Retail transformation rarely fails because of technology; it fails because of organizational barriers. Misaligned incentives, cultural resistance, legacy processes, and leadership blind spots can quietly undermine even the most promising digital and AI initiatives. For senior retail leaders, these hidden obstacles often prevent AI pilots from scaling, stall transformation efforts, and limit the return on innovation investments. This session introduces a practical framework for identifying and addressing the internal challenges that hold transformation efforts back. Attendees will hear strategies for aligning teams, modernizing decision-making, and building organizations capable of turning AI and digital initiatives into sustained, measurable business impact – moving beyond experimentation toward enterprise-wide change.