We asked our 8-year-old son if he was willing to help out and have a female classmate ride home with him today. He wasn't sure. If he didn't do the right thing and said no, he would hurt her feelings. If he did the right thing, he worried that he would be uncomfortable spending time with her. When they are eight years old, boys think girls are yucky.
This is the same dilemma that salespeople face every day, in every sales call, in every interaction. Do the right thing and ask the tough question that the situation calls for; or do what's comfortable and present.
Our son made the right decision and was rewarded for leaving his comfort zone. They had a great time together. The funny thing is that it was only the decision that was difficult. Once he had made the decision it was VERY comfortable.
The same will be true for your salespeople. The only part they will struggle with is THE DECISION to do the right thing by asking the tough question. Once they've made the decision, the actual question they ask will be easy too.
Which of your salespeople get uncomfortable and when?
How can you get them to leave their comfort zone?
Simply role play it with them until it's easy for them and it comes automatically.