Mid to large enterprises from all sectors across the globe have embarked upon their intelligent automation journeys – posing challenges and necessitating decisions that are fundamentally different from traditional IT programs. The March 2019 edition of the HOLMES Advisory Board meeting witnessed leaders from across industries discuss the challenges faced while implementing AI transformation, and how they overcame it. While the Board members acknowledge that there can be no single path to success, a framework to approach the enterprise automation journey is most advisable. Outcome based POCs are preferred over big-bang initiatives. Although traditionally, cost has been the most important criteria for automation projects, with the advent of AI, employee and customer experience is fast becoming a major KPI for success. A people-first change management methodology is the way to go!