We actually do know when the last time people did roles and the related types of information.
If you just hover your mouse over a person in the drop-downs in the dated agenda editor... look at the "mini-report" that shows up in the tool-tip. It is the same sort of information that Queasy-Speak is using to make the decisions for you.
We may provide some sort of automated approach in the future, but there would be a lot of guardrails and limits placed on it if we did that.