Generate a List of Questions for a One-to-One Meeting With Your Manager

Most one-to-ones are status updates that could have been an email, or silences that both people fill with the path of least resistance. This generates twenty questions worth asking across four areas: your performance and development, the team and organisation, the relationship with your manager, and your future in the role. Includes at least one question in each category that is worth asking even if it feels uncomfortable.

You have a one-to-one meeting with your manager coming up and you want to use it well rather than let it drift into a status update or an awkward silence. Generate twenty questions worth asking in a one-to-one, grouped into four categories: questions about your own performance and development (what is going well, what the feedback on your recent work is, where your manager wants to see you develop); questions about the team and wider organisation (what is changing, what priorities are shifting, what the manager is dealing with that affects the team); questions that build the relationship (what would make the manager's job easier, what is something the team does not know that would help them); and questions about your future in the role (what the path forward looks like, what would make you promotable, what the manager would want you to learn in the next six months). For each category, include at least one question worth asking even if it feels uncomfortable.