Thanks, James. I can see that I haven't clearly explained how those part of the system come in to play and interact with each other. That will definitely go into my 'changes for the next draft' list.
Let's see if I can explain it more clearly, here ...
The intention is that you play the game in two phases: a conversational, back-and-forth exchange of Goes followed by a period of downtime (called 'Evaluation'). Evaluation is the primary source of Stress and Insight for characters.
When you're having your exchange of Goes, you're as in the fiction as possible, trying to create the reality of this Manager-Employee relationship.
When the exchange of Goes come to a natural end-point (or if neither of you are sure what to do next), then you go to Evaluation. That's where you assess how much Stress the Employee just earned and how much Insight they got into the bullying dynamic of their relationship. The players can then take the Stress and Insight with them into the next exchange of Goes and spending them to unlock new abilities.
Both characters can also earn Stress and Insight when the employee takes 'damage' from what the bullying manager has done to them (that's the 'Broken' and 'Transformed' stuff you pointed out, James.)
--- --- ---
Man, I hope that's clearer (I have a head-cold at the moment, so I have no idea!) I'll take a look at the rules and see how I can make it clearer, there.