How to Raise a Difficult Issue in a One-on-One with Your Boss

Raising a potentially emotional topic to your manager can be difficult — you don’t know how they will react or whether you will be judged or punished in some way. Based on the science of conflict resolution, dissent, upward communication, and the authors’ own research on one-on-one meetings, they share a clear process for raising these issues with your manager. It involves first recognizing the importance of one-on-ones to you, the direct report; then clearly understanding the core need you are trying to address. Then it’s a process of picking your battles carefully, preparing yourself, starting well, executing with composure, curiosity, and a willingness to adapt, and finally wrapping up while maintaining momentum.