Here are a few of my favourite sales questions for uncovering prospects’ issues. Some more direct than others. Enjoy!

• How have things changed in company/industry in the last few years/ months?
• (If they tell you about a recent project or initiative) What do you think are the biggest “lessons learned” from this project? How would you do things differently? With the benefit of hindsight how would you run such a project again, if you had to?
• What are the biggest developments in the industry? How are you keeping up with that? What do you think that will look like in the future?
• What’s most important for you; X, Y or Z? (change as required, e.g. “increasing market share, generating new sales or raising profitability” or “finding good people, lowering staff turnover or finding a way to cut the number of sick days taken by staff?”)
• What are the biggest challenges you face with (department, business, industry, product, etc) right now?
• What are the big initiatives you are working on right now? What issues have you faced in achieving these?
• What are the big changes in (department, business, industry, product, etc) right now?
• What’s the “big goal” at the moment? What’s standing in the way of you achieving that?
• (When they talk about a current project or initiative) Are those the results you hoped/planned for?
• What’s the number one most important thing for you/ your boss/ company/ industry/ customers now?
• What’s the number one most important thing for you/ your boss/ company/ industry/ customers now going into the future?
• A lot of companies seem to be having issues with (Problem X, problem Y and Problem Z) right now. Is that your experience too?
• Do you think (problem X) is more of an issue than (problem Y?)
• What do/does your boss/ company/ industry/ customers complain about / struggle with?
• What changes do/does your boss/ company/ industry/ customers want to see?
• What do you think is going to cause the biggest changes / threats / issues in your business in the next X years?
• What would you like to achieve from today’s meeting?
• What have been your biggest successes in (area X)? What else would you like to improve on?
• What's keeping you from perfection in X, Y or Z?
• If you had no limitations, no budget restraints, no (other problem), what would you aim to do? (now work back to find the problems that are a barrier to them achieving their goals)