Successful Copilot adoption doesn’t come from flashy demonstrations. It comes from practical use cases and organizational readiness. Drawing on real-world experiences from enterprises deploying Copilot, this chapter highlights patterns that influence success or failure. Readers will explore common pitfalls such as unrealistic expectations, poor data hygiene, and one-time evaluations of AI tools. The chapter concludes with guidance on how organizations can move from experimentation to meaningful productivity gains with Copilot and agents.