Almost 19 years since Agile Manifesto was published, organizations are still struggling to adopt and mature Agile. There is no one-size-fits-all when it comes to Agile transformation strategy, but plenty of learning from other successful/ failed initiatives. I will discuss one of the crucial prerequisites of Agile transformation, Cultural assessment, referring to some of the popular models, such as Schneider and Laloux. But most importantly which framework would be most suitable, mapping to cultural type of a department/organization. Not limiting to Scrum, or Kanban, but considering other methods such as Lean, Design Thinking, DevOps etc, to formulate one that aligns with organization's culture. At two levels, first Adoption and then Scale (Scale -up or -out). Along the way, I will share insights from my experience, some use cases, from working across organizations of various sizes and shapes, and the factors that enabled success in their transformation journeys.