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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?”

About the Author

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.

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