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100+ Sales Questions

I'd like to share my favourite sales questions with you all. A few things to note :
  • Some questions are versions of each other
  • The questions need to be used at the right time, in the right context, with the right buyers in the right situation - they are not magic "silver bullets"
That's it! thmbp2; I hope you find them useful - and add your own at the end of this post!

Ed McLean, SalesItch


To Uncover Problems

• 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?


To Investigate Problems

• Why/how is that an issue?

• What is this costing you?

• Who else is affected by this issue?

• How does that impact the business/ department/ you?

• Why does that matter?

• What’s driving this?

• What’s motivating you to take action on this?

• Where does this initiative come from?

• Where (in the organisation) did this problem start?


Qualify prospect's seriousness

• Why do this now? Why not next month, or next year?

• What happens if you DON’T (solve this issue)?

• If you can’t find a solution to this, what do think will happen / what will that mean for you/ the department/ company?

• Why does this need to be done?

• Why is this important? Why does it matter? Can’t you just stick with what you’ve got?

• If you get this up and running, how does that change things? What does it do for you?

• What are the key reasons that you are doing this for?

• Have you ever tried to do something similar to this in the past? What stopped you that time?

• From what we have discussed, what are the most important issues to you?


Uncover problems in incumbent supplier

• How do you feel about (incumbent vendor)?

• What do you like/dislike about company / product?

• What would you like to improve upon?

• How could it be better?

• When you were talking to (incumbent vendor) initially, what did you decide they had to achieve? Did you/they achieve that?

• If you think back to when you started this, what were your success criteria? What was it you were hoping to achieve? How does that compare with what you got? Why do you think that is? What improvements/changes could be made?

• How have your needs / the market changed since you got your solution from (incumbent vendor)?

• What would your perfect product/vendor relationship look like?

• What are your criteria for selecting suppliers?

• What would really put one supplier ahead of another?

• What alternatives are you/ will you be looking at for this?

• What are you looking for in suppliers?

• What are your three most important criteria for selecting suppliers?

• How do you go about selecting suppliers?

• When you look at (incumbent vendor), how do you know whether they are doing a good job for you – how do you measure their performance?

• Thinking ahead a few years from now, what do you think you will need from your vendor?

• What was behind your decision to go with (incumbent vendor)? Does (incumbent vendor) still do that for you?


Confirm understanding

• Does that some