Here's 10 of My Best Questions to Ask:
When you ask a question, there are ways to determine whether or not you have a good shot at getting to yes which is by asking qualifying questions first.
Simply stated, you won't get the business if you don't ask (which is why I say that asking for the business is one of marketing's "magic bullets"), but you will increase your chances of getting a positive response if you qualify first.
And frankly, asking for the sale without first determining need, interest, and inclination is rude, presumptive, and off-putting. Why? Because offering a solution without first assessing need is like a doctor writing a prescription before the diagnosis - not a good idea for anyone!
Here are some questions that might help you assess the need and get to yes:
1. What is the goal or outcome you want to achieve? Or as an alternate: If you could wave a magic wand and this issue would be settled to your satisfaction, what would that look like?
2. Who else needs to be involved in this decision?
3. What will happen/what are the consequences if you don't do this?
4. What are the obstacles in your way right now?
5. What are the resources you have to draw on?
6. What is your timeline for reaching this goal or completing this project?
7. How will you measure success? How will things be different?
8. Have you tried to solve this problem before, and if so, what happened?
9. Why is this important for you to solve right now?
10. How will you feel once this is complete?
Once these questions have been asked and answered, you can present your solution as an option, because then, ostensibly, you are in a position to make an informed recommendation.
Your prospect will feel more confident in your proposal because you spent the time to really understand the situation before you offered a solution, rather than throwing a one-size-fits-all solution at the problem.

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Chris,
Today it is truly like pulling teeth to get some people to open up....we must get the potential customer to trust that we are there for their best interest.