To paraphrase Lincoln，

"If I can get the job done by asking all those questions, I will do it; If I can get the job done by asking no question, I will do it; if I can get the job done by asking some questions while skiping other questions, I will do it."

You have a nice boss who is willing to help. No need to over analyze it.

philosophically, I take people's words as their bond. If they slip, it's their peoblem, not mine :)