June 16th, 2015

Some of the Best Open-ended Questions for Winning Sales

open-ended questions

What are Some of the Best Open-ended Questions for Winning Sales?

There is no magic wand to reveal the five best open-ended questions to ask for all sales situations. That’s the bad news. The good news is, there are several ingredients that will make asking five great questions easier. Here is the recipe for success:

Remember the old joke, “Where does an 800-lb. gorilla sit? Anywhere it wants to.” Don’t be that gorilla, starting the questioning dialogue with the questions YOU want answered. Start the sales dialogue by asking about the client’s short-term objectives and needs. This approach allows clients to take the conversation where they want, so they can share what is top-of-mind for them, what keeps them up at night, and what is most important to them in the near future. Even though you control the conversation by the questions that you ask, let the clients control which areas they want to direct the conversation.

Here are some sample questions to consider and adapt, as appropriate:

  • “In speaking with your senior account manager, he mentioned three key drivers: X, Y, and Z. What specifically are your key objectives related to these drivers?” (This question leverages your preparation so that the question doesn’t feel too basic or unprepared.)
  • “What are you trying to accomplish in the next six months?”
  • “What is most important to you in your business right now?”
  • “What has prompted the shift in strategy from X to Y?” 

Ask a variety of questions to get all of the key areas on the table.

It is easy to start asking questions to explore the areas that YOU want to focus on, which typically involve your product, service, or ways to move the sales cycle forward. It is a little harder but better in the long run to forget about your objectives for the call and the questions that go with it.

Here are some areas that usually get neglected in a sales conversation:

Personal needs:

  • “What is at stake for you?”
  • “What do you look for in a partner?”

Future needs:

  • “What are your expansion plans for the next two years?”
  • “What are your long-term strategies?”

Implementation needs:

  • “What is the decision-making process in your organization?”
  • “What have you allocated for this project?”

Even though you will be letting the client take the lead on conversational topics, you still need to plan specific questions during your pre-call preparation. You should be able to plan half of the questions necessary ahead of time, so take advantage of this prep. For the other half, allow some flexibility for questions that come up during the conversation and during your follow-up probing questions. Don’t become fixated on the questions that you planned. The best conversations are ones in which you follow the client’s lead.

The type of questions that you ask will determine how the client perceives you: as a vendor or as a partner. The more generic your questions, the more generic the sale. You also lose the opportunity to use the client’s own words to position solutions or uncover additional opportunities.

The most important, open-ended question in this blog post is, “What is your questioning strategy for winning sales?”

Learn more about Richardson’s Consultative Selling Sales Training Solutions.


About The Author: Karen Klein

Karen Klein is a Senior Training Consultant and Executive Coach with Richardson. She has worked with global clients in the US, South America, Europe and Asia, spanning different industries. Prior to working with Richardson, she was an Account Manager and then District Sales Manager for a telecommunications company, where she was in charge, among other things, of improving the employee job performance. As a consultant, Karen has worked in conjunction with the Puerto Rico State Department, researching and conceiving innovative market strategies and cost-effective measures for improving its economic activities with sister states. She collaborated with Microsoft Mexico to help increase the effectiveness and efficiency of the company’s call center; and she analyzed and assessed the effectiveness of General Motor's operations in Hungary, and developed a case study that was distributed to international executives attending business school at Georgetown University. She is bilingual in Spanish and English and fluent in French and has lived in Europe and the US.

Karen Klein

4 Responses to “Some of the Best Open-ended Questions for Winning Sales”

  1. June 16, 2015 at 11:37 am, Richard J Orlando said:

    Enjoyed your post today Karen. You hit the bullseye here. Yesterday a new B2B Global 2000 prospect asked us about our company at the beginning of our call. My rule of thumb is after 5-7 minutes if the prospect doesn’t speak in a complete sentence to us, I stop and ask an open ended question. After 5 minutes, I asked, “What are your challenges with reps presenting YOUR value proposition?” After 10 minutes, we had great information from the prospect, and, he started asking us questions. I really enjoyed reading your post. Thank you.


    • Karen Klein

      June 16, 2015 at 12:35 pm, Karen said:

      Richard, thank you so much for sharing such a poignant example of the virtues of asking good open-ended questions. Glad to hear your prospect call was a success and thank you for taking time to give me your feedback, it made my day!!!


  2. June 16, 2015 at 5:33 pm, Nancy Bleeke said:

    Very much agree with your well noted post Karen.

    Our winning strategy for questions includes what you noted and to make sure we aren’t only focusing on needs. That we also focus on problems we can solve, opportunities we can help them capture, and the emotional wants that end up driving the urgency and decision.


    • Karen Klein

      June 19, 2015 at 6:34 am, Karen Klein said:

      Nancy, thank you very much for your post and your wise distinction between needs, problems and the emotional aspect embedded in sales which is very important.

      We at Richardson also use question categories that focus on the current situation and level of satisfaction with that situation, to uncover problems, challenges, opportunities as well as ideal situations to their current modus operandi (i.e. What do you like about X? How is it working? What can be improved? What challenges are getting on the way? And ideally what would they like to see improved/differently?)

      Have a great day, and sorry for the delayed response. I Have been on a transatlantic trip.


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