The Challenges of a Reorg Leader

I think the biggest piece that I heard about that is really what you started with, is double clicking with each individual team member. That kind of feeds into the next thing that I was interested in understanding is some of the typical challenges that one could run into in a reorg. The multiple iterations from your ideal state of what that org chart should look like, and then going through iterations of what's really feasible with current resources. What other challenges, maybe were you not expecting to run into that popped up their heads?