Great sales people ask thought provoking questions. However, thought provoking questions are the toughest to ask. They just make you downright uncomfortable. Solution? Cushion the question! Cushioning is opening and closing the question with a soft statement, re-framing the ‘tough’ question into a ‘soft’ ask. For example, first open with something like “Out of mere curiosity…” or “This may be a bit premature to ask, but…” followed by your ‘tough’ question. Immediately after that, close it with another cushion, such as “Thought it was worth picking your brain about it,” or “Just looking to see what it’s like to be in your shoes.” You’ll be pleasantly surprised to see those ‘tough’ questions being answered quite comfortably.