One of your biggest challenges as a leader is having difficult conversations with members of your group. These conversations may be necessary for a variety of reasons: (1) they might be underperforming or out of compliance with documentation or billing; (2) they might have conduct that is detrimental to the team; or (3) they seem to be struggling with the team concept and the overall goals of the group. Your success as a leader will be determined primarily by how well you conduct one-on-one meetings, working with “problematic” group members to help them be successful or to find a different path for them, sometime even “managing them out.” This chapter discusses how to have these difficult conversations, using case examples to illustrate different techniques. It goes into how to set up the meeting in advance, setting clear expectations and the right mindsets. It discusses how to plan in advance for how you’d like the meeting to go, as well as having a plan B and plan C for when things don’t go as intended. It discusses how to conduct the meeting, including who should be in the room when it happens. It also describes necessary documentation and follow-up from these meetings, as well as setting expectations and next steps. It concludes with the particularly difficult situation of removing someone from a leadership position.