[chrisbro]

We have had success at my org by anchoring a lot of the mentor/mentee discussion around our documented career ladder. If there's not a pressing specific discussion topic for one of their meetings, they can always bring that out and go through the ladder items to brainstorm ideas on how to progress.

We also recommend mentors to sit in on some agile ceremonies with the mentee's team to get a feel for how the mentee's dynamic is with their team, which can spark some discussion as well.

Fundamental, long-term issues can include encouraging the mentee to be more assertive, how to help their team become more effective, and how to approach navigating the inevitable politics of the organization.