I surprised my family last year by booking a night at The Ritz-Carlton in Buckhead.
I called the night before our departure to ask, "What time is checkout?"
My real question was actually, "Will we have time to do what we want tomorrow before we have to check out of the hotel?" Of course, I was afraid to ask that of the front desk employee. Fortunately, the she heard my real question and replied, "Is there a certain time you would like to check out?"
I was surprised by her question back to me.
I told then her what we wanted to accomplish, and she replied, "Normal checkout is 11am. But how about this? We can set your checkout time to 1pm, so that should give you plenty of time to enjoy whatever you're going to do. Would that be helpful?"
When guests (or employees, volunteers, family, friend, etc.) are communicating with you, really listen to what they are asking. You will make them feel heard. You will better be able to offer a helpful response. That goes a long way.
Listen to the question behind the question.