Paul had made the observation that many technology leaders might be doing their subordinates’ jobs instead of their boss’s jobs. So, during a breakout session, I asked him to do a role-play with Jeff Gallimore, where Jeff played his boss, demonstrating a lack of interest in having Paul take over his role.

It was an exceptional modeling demonstration of how to initiate such a conversation, and what to do when there are clearly issues that need to be fixed beforehand.