We faced a similar problem. We've got a strong 1-on-1 culture in our startup but often struggle with what to talk so we created an ultimate list of one-on-one questions (500+) with a social flavour https://www.peoplebox.ai/t/one-on-one-meeting-template-manag...
These are for managers but can be flipped to find agenda/ questions for direct reports.
These are for managers but can be flipped to find agenda/ questions for direct reports.