How to Overcome Social Awkwardness When Asking a Question

One of the questions that i like to ask is, what could i do or stop doing that would make it easier to work with me? I borrowed this from fred coffman, my coach when i was when i was at google. What you want to think about here with your go to question is, what's the quest on that will seem natural coming out of your mouth? Also, what's a question that can't be answered with a yes or a no? So jason rosolph, who i started radical canter with, told me that he hated my go to question because it was so open ended. And so need to overcome tat social awkwardness and just pause