Was there a compelling event that caused you to "attend our webinar - download a whitepaper - launch a trial" etc? If they say yes that is great you can build your message around that event. If they say no you need to qualify fully before spending too many sales cycles.

This is an interesting broad brush look at trends in sales questions. It's hard to generalize because questions that are used in selling conversations are dictated by situations. Another interesting discussion would be learning what salespeople must discover. A blog I just released on this topic "The Right Sales Questions Will Uncover Enterprise Risks and Golden Opportunities," http://www.customerthink.com/blog/the_right_sales_questions_will_uncover_enterprise_risks_and_golden_opportunities

I really thought about skipping this, but what the heck, it's about sharing content. "Pretend you're me, talking with you and you're wondering, 'What should I ask now?' What question would you ask?" Whatever my prospect answers, I answer, "Interesting.....Why would I ask that?" As an aside, my old post, Ask me a question! received more comments than any of my other posts EVER! (and gave me some blog fodder.)

The questions I would ask would be more geared towards figuring out what the long-term vs. short-term fixes.  
 
Short-term fixes are usually only a sub-set of a longer-term problem, and making sure that their short-term "fix" is really addressing the need. Something like, "So we've talked about problems X and Y, and it sounds like we may be able to help you with that--but to make sure that we're really going to be a good fit for you, 12 months from now, what's the one, single problem you never want to have to revisit, and have we really gotten there yet?"

Getting to the underlying business issues driving projects can be some of the most difficult information to pull out of a prospect. Some prospects will go to great lengths to hide this information because you haven't earned the right to ask. The right to ask questions and trust has a direct correlation. That said one of the questions I like to ask is this. "Lets say I am the CXO with the money you need to bring in a solution. I give you funding to get the technology and I come back to you at some point after implementation and say, hey great I see you have XYZ up and running now, how is it helping our business? What would your response be to me?" If the prospect answers with some bits and bytes feeds and speeds answer you have a challenge on your hands. Prepare to be as much of an educator and facilitator as a sales guy trying to hit quota. You will need to get them thinking about how your solution will help their company generate revenue, reduce costs, improve efficiencies, or mitigate risk.

Hi Matt! Interesting topic, well I think for me, my favorite / go-to sales questions to move a prospect forward would be : " What is the approximate budget that you have set for this project?" The reason why I ask my clients this  
 
question is that- at least I would have an idea on what options I can give to my clients. http://bit.ly/ayeen