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Asking Sales Questions to Engage Prospects

Salespeople who call on prospects or clients without well-researched, well-prepared sales questions to ask are likely to walk away knowing little more than when they began.

The four main objectives in any initial sales dialogue should be these:

  1. To establish yourself as a credible professional and partner by being prepared and thoughtful in the sales questions that you ask
  2. To seek to understand the prospect’s current situation, which includes an effort to validate what you’ve researched or the assumptions that you’ve made
  3. To uncover a broader and deeper range of information, from strategic objectives to immediate business needs
  4. To seed new ideas to either influence or disrupt the prospect’s current thinking

Asking Open Ended Sales Questions

With those four objectives firmly in mind, your next step is to develop a series of open-ended questions that you will ask to engage clients in a meaningful dialogue. Sequence your sales prospecting questions to create a flow. Forget about yes-or-no sales questions. Don’t provide multiple-choice answers. You want each question to elicit a thoughtful answer from the prospect’s or client’s point of view.

  • What is the initiative we’re here to talk about today?
  • What is the driving force behind this initiative?
  • Why is now the right time for this initiative?
  • How will you recognize or define success?

Pacing Your Prospecting Questions

Just as important as specific sales questions are the skills of listening and pacing. It can be tempting to fire off questions, one after another. But for the prospect facing a barrage of questions, the conversation can seem more like an interrogation.

The best approach is a conversational one. Ask a question. Listen for the answer. Acknowledge what the prospect says, and check your understanding of the answer. Then, ask a follow-up question. You want the discussion to be free-flowing and enjoyable, not a checklist to march through until each question is asked and answered.

Structuring Your Sales Questions

Another element to consider is structure. You want to start with a high-level perspective of the situation and then drill down into various aspects:

  • 30,000-ft. view: Tell me about the initiative that we’re here to talk about today.
  • Current strategy: How have you been addressing this issue?
  • Cultural aspects: What changes do you want to see in your organization? What do you want your people to be doing differently?
  • Influencing ideas: Have you thought about this aspect? It’s something we’ve helped other clients address with XYZ.
  • Decision criteria: What is your time frame for getting started? What does your decision-making process look like and who will be involved?
  • Special circumstances: What sensitivities do I need to be aware of?
  • Must-ask question: What have I not asked that I need to know?

The Importance of Preparing Your Sales Questions in Advance

Whenever a prospect or client agrees to take your call or a meeting, go in prepared. You need a developed questioning strategy with supportive, engaging, and open-ended questions.

At Richardson, we believe that the sale is made in the dialogue and that you want to start a dialogue that uncovers the information you need while positioning yourself as a partner and value-added resource in the process.

The most important thing to remember about sales questions is this: Don’t wing it. The other party will quickly see through your lack of preparation and feel less valued as a client.

If the sales opportunity is one you want to win (and aren’t they all?), then don’t waste the prospect’s time or your own. Go into each meeting prepared to engage the other party, and then begin the very human task of establishing a meaningful relationship.

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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