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Best Sales Questions that Work

You may love watching police dramas on TV, but a good salesperson never recreates the interrogation room in a prospect’s office.

The foundation of a good sales questioning strategy is creating a well-paced dialogue based on asking open-ended questions.

Here is a list of questions that I typically draw on in developing my pre-call strategy. They can be easily honed for specific situations and are intended to draw the other person into a meaningful conversation.

What is the opportunity?

  • What is the initiative we’re here to talk about today?
  • Why is now the right time for this initiative?
  • What is the driving force behind this initiative?

What are the expectations?

  • How will you recognize or define success?
  • What changes do you want to see in your organization?
  • What do you want your people to be doing differently
  • How do you see this working within your organization?
  • What are the roadblocks?
  • Are there any champions or other stakeholders with an interest in this initiative?

What are the circumstances?

  • How have you been addressing this issue?
  • What is your time frame for getting started?
  • What does your decision-making process look like, and who will be involved?
  • What are next steps and your time frames for implementation?
  • When can we schedule time for a presentation to all of the decision makers?

Who else is in the running?

  • Who else are you considering as a partner for this initiative?
  • What criteria will you use in making this decision?
  • What have I not addressed that you’ve heard about and are intrigued by from other potential partners?

What else might you ask?

  • Have you thought about this aspect? It’s something that we’ve helped other clients address with XYZ.
  • What sensitivities do I need to be aware of?
  • What have I not asked that I need to know?

Whichever questions you ask, keep these tips in mind during any sales questioning:

  • Avoid yes-or-no or multiple-choice questions.
  • Avoid asking multiple questions at once. Pose one question at a time, and wait for the answer.
  • Listen closely to the prospect’s answer and, when appropriate, let it set the direction of follow-up questions.
  • Never answer your own question; let the prospect speak instead.
  • Never formulate your next question while the prospect is answering the previous one. Keep your attention on the prospect’s answers. Good listening goes hand-in-hand with good questioning.

Questioning is one of Richardson’s Six Critical Skills for sales.

  1. Presence: Ability to project confidence, conviction, and interest in body language and voice
  2. Relating: Ability to use acknowledgment, rapport, and empathy to connect
  3. Questioning: Ability to explore needs and create dialogue
  4. Listening: Ability to understand content and emotional message
  5. Positioning: Ability to leverage client needs to be persuasive
  6. Checking: Ability to elicit feedback

These are the skills that allow salespeople to create a meaningful dialogue; establish themselves as trusted advisors; understand client needs, priorities, and perspectives; and close profitable business. Each skill builds on and supports the others — and, at the heart is the ability to ask the right questions to move your sales opportunities forward.

About the Author

Richardson is a global sales training and performance improvement company. Our goal is to transform every buyer experience by empowering sellers with critical skills so they can create value to buyers and drive meaningful conversations. Our methodology combines a market proven sales and coaching curriculum with an innovative and customizable approach to learning that ensures your sales teams learn, master, and apply those behaviors where and when it matters most — in front of your customers. It’s our job to anticipate change in your industry so that your sales team can focus on fostering long-term relationships, becoming indispensable partners for their buyers.

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