Implementing a behavioural health programme involves more than simply providing training to healthcare providers. System-wide behavioural change is necessary, often including prevailing attitudes, values, and mindsets. This process frequently involves multi-faceted, deliberate activity across an organization’s many levels (clinicians, teams, administrators, managers, etc.). As a complex, multi-modal treatment for severe and life-threatening problems, implementing DBT presents unique challenges. A dialectical stance which finds a synthesis between opposing, but true, ideas helps resolve the inevitable tensions associated with introducing and sustaining DBT. This chapter identifies three dialectical dilemmas which commonly occur when implementing DBT, and offers examples of each from real-world projects. It discusses the tension between adopting DBT with full fidelity and adapting it in response to the context in which it is delivered; the tension between short-term risk management decisions and persisting with DBT delivery and maintaining a long-term view; and the tension between meeting both the organizational system’s needs and the needs of people delivering the treatment. Finally, it offers practical suggestions for those considering implementing a DBT programme.