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Best Sales Questions that Work

open ended questions


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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 recognise or define success?
  • What changes do you want to see in your organisation?
  • What do you want your people to be doing differently
  • How do you see this working within your organisation?
  • 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 Sales Performance’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 acknowledgement, 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 advisers; 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.
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