This chapter discusses some psychological challenges for the leader as an individual and includes a brief discussion of attachments and biases that can hinder progress towards brave action. It considers the role of both intuition and critical thinking at the implementation stage. The chapter identifies challenges arising as a result of external factors. These include stakeholder concerns and tensions such as those between the commercial and financial needs of the organization and conflicting quality or service needs, many of which are exacerbated if the leader tries to go it alone when implementing decisions. The chapter examines a complex responsive approach to implementation, which takes account of social and relational aspects of the organizational structure, examining the skills and strategies that can help deliver smooth implementation and considering the role of the coach in this situation. It provides several coaching examples of where leaders were alerted to their biases and how strong emotion might on occasion adversely affect their thinking.