36 Questions Any B2B Salesperson Can Use to Shorten Their Sales Cycle

It's no secret that great questions are the key to shortening the B2B sales cycle.  That mystery was solved with Neil Rackham's SPIN Selling research.  Salespeople that ask resonating questions win more business, faster than those who ask average questions.  

So, this morning I challenged myself – how many questions could I come up with in 30 minutes that any B2B salesperson could use to shorten the sales cycle and increase their win rate. Here are the 36 I came up with:

1. If we were having this conversation 3 years from now, how would you know that the initiative was successful?
2. On a scale of 1 – 10, where 10 is sign me up I’m ready to go and 1 is this is the worst idea I’ve ever heard, please get away from me; how would you rate your feelings about moving forward with our recommendation?
3. Where does this initiative stack against the other initiatives in the company?
4. What are the barriers you face to achieve the results you just shared with me?
5. What is the biggest barrier?
6. What gives you confidence that you/your company will be able to achieve those results?
7. I’m curious, when you mentioned [fill in with the appropriate content], what did you mean by that [or what were you looking for]?
8. What’s causing you/caused you to begin looking for [your product/service]?
9. How does your [fill in with appropriate content] process work today?
10. How are you managing the situation currently? What’s working about that? What’s not working?
11. If you could wave a magic wand, what would you change about [fill in the blank]?
12. What is the probability that you’ll move forward with a solution in this area in the next 6 months? 12 months?
13. Help me understand, when your company embarks upon making a decision like this, what process does it follow? Who’s typically involved?
14. How will [fill in the blank] be evaluated?
15. What’s going on in your business these days? How are things changing?
16. How do you plan on managing the trade-offs between minimizing the price, enhancing the quality and managing service levels?
17. When you’ve engaged in these types of initiatives in the past, what were some of the mistakes you made?
18. What reasons would you consider changing suppliers for?
19. What is the timing that you need a solution in place and fully functioning?
20. What factors do you view as being the most important in ensuring that you choose the right solution?
21. What steps have you already taken to move towards getting your desired results?
22. What impact is the[describe situation] having on your [describe initiative, solution and functional area]?
23. What are you doing today to ensure that you continually improve your results in the future?
24. When you sit with your direct reports, how do you judge how well they’re doing?
25. When you’re being evaluated, what criteria is used to determine how well you’re doing?
26. How does that affect your compensation?
27. What’s holding you or the company back from improving [fill in blank]?
28. What are you doing to exploit your competitive advantage?
29. How is your competition impacting your ability to [fill in area of focus]?
30. If I were to follow you around for a week (don’t worry, I’m not going to do that), what are the most pressing issues I’d see you deal with?
31. What are the most important issues?
32. What are the biggest challenges you’re unable to focus on currently?
33. What’s prevented you from taking action in this area before?
34. If the decision you make is a good one, how will that impact the overall business? How will it impact you?
35. If the decision you make isn’t a good one, how will that impact the overall business? How will it impact you?
36. Tell me more… (While technically that’s not a question, it works like one and it’s one of the most effective questions I’ve ever used.)

Thirty minutes is up. I hope you enjoyed (and more importantly use) the list I came up with. What did I miss? What questions do you use?