Ask HN: Can AI help solve asynchronous communication gaps?

Problem: In async communication (e.g. leaving message to someone 5+ timezones away - and seeing their response only the next day) #1 reason for the time lost is that when I leave a task/memo for someone and forget some important detail - I only learn the next day that the work has been on hold because the other person had been waiting for my response to their question.

A possible solution would be an ML algorithm that analyses our previous communication and structure of the memo - and immediately asks me the questions that would most likely arise.

My question to AI wizards: is this technically feasible in the current state of technology?