Tricky Situations with Lisa Olsen

You likely have at least one story that starts with "so this happened, and I had no idea what to do." The kind of situation that's specific to your executive, your office politics, your particular flavor of chaos, and doesn't come up in the usual training material because it's too weird, too sensitive, or too close to something still unfolding.

Tricky Situations is a recurring, live-only conversation for exactly that. Bring the thing you're dealing with, or the thing you dealt with last month and still can't quite put down, and talk it through with a small group of peers who understand the nuance of the job. There's no recap, no case study, no polished takeaway to skim afterward. Just a conversation with people navigating the same kind of terrain, in a room safe enough to say the real version out loud.

Given how candid these conversations tend to get, sessions are not recorded, and nothing discussed is shared afterward, anywhere. What's said in the room stays there. The only way to get anything out of this one is to show up live. This is a Pro member benefit.

A note about the session image: the background is a stylized, duotone edit of "The Choice of Hercules" by Annibale Carracci, painted in Rome in 1596. Cardinal Odoardo Farnese commissioned the piece for the ceiling of his camerino (private study) in the Farnese Palace. The scene depicts Hercules as a young man at a crossroads, flanked by two figures personifying Virtue and Vice, representing the right way and the easy way, each gesturing toward a different path.