A Lean Six Sigma implementation, like any organization-wide initiative, has its own challenges and pitfalls. Over the period, many organizations have implemented Lean Six Sigma, and they have had their own fair share of these challenges and unique ways to overcome them. This chapter discusses some of the best practices and challenges that these organizations have followed and faced in the course of the implementation. This will help us steer away from the potential pitfalls and leverage the learning and the best practices.