Not having this skill is the bane of my existence! There is always a person who complains* that I provide too little detail ("you need to be more rigorous/specific/careful how you define") or too much of it ("we are getting too much into the weeds here" or they just tune out). I asked a much more senior person for feedback and it is always too much or too little when go from one revision to another.
* Yes, it is better that they articulate what they don't like than just completely ignore it and leave me in the dark.
