One of the skills of a good communicator is to know how many layers of a story to tell. It takes some savvy and judgment to assess what the listener really wants to know and to tailor your response to this.
For example, if someone at an airport asks you where you are going, you have many choices from which to respond:
> To Tennessee
> To Knoxville
> To the Hampton Inn in Knoxville
> To Knoxville to go to…. and then share your reason for travel
If it is a casual chat, I may not care for a level of detail and description of the many layers of your journey. But if I am your supervisor talking about a project, the equivalent “to Tennessee” answer will be insufficient. In that conversation, I may want to know not only the “Hampton Inn” equivalent, but maybe even what room and what time you will arrive.
It is worth the time as a supervisor to have explicit conversations with your staff about the level of information that is routinely comfortable for you to have and the method by which you prefer to have it. You can’t fault your staff for telling you too much or too little if you haven’t shared with them what is just right.