Management and leadership require skill in having tough conversations. Increasing your leadership and management capabilities will serve you and your team well. Delivering bad news is one of the worst aspects of a manager’s job. It can be especially difficult when you’re delivering bad news to someone who’s trying to succeed and grow — but didn’t quite make the grade. Going into the conversation, you know they’re going to be disappointed and will have a lot of questions — some of which might be difficult to answer.