July 29th, 2015

Asking Sales Questions to Engage Prospects


The Best Sales Questions to Engage Your Prospects

“If you fail to plan, you are planning to fail.” — Benjamin Franklin

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.

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

consultative selling sales questions

About The Author: Beth Eames

Beth is a Regional Vice President with Richardson. As an advisor and consultant, Beth works with her clients to assess sales organization processes and performance, sales methodology, and talent acceleration to drive the development and performance of desired outcomes. She is responsible for managing strategic global client relationships, as well as new business development. Beth has extensive experience working with a broad base of clients in multiple industries, including financial services, insurance, technology, pharmaceutical, and professional services.

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4 Responses to “Asking Sales Questions to Engage Prospects”

  1. July 29, 2015 at 12:16 pm, Richard J Orlando said:

    Well done blog about the art of asking open-ended questions. There’s a fine line, that you address well, between “asking” and “interrogating”, especially with our customers who are B2B Global 2000 enterprises that use our value proposition cloud-based tool. Our sales users tell us they have success mixing 3-4 open-ended questions with 3-4 quantified “typical results similar customers” have experienced economic value using our offering. For example, reduced labor costs by $1 million, increased revenue by $10 million etc. With 60% of decisions ending in “no decision” , I would not leave the meeting unless the customer knew your value proposition. I think using your technique for open-ended questioning is great, and, combined with a solid value proposition will result in more qualified deals getting into your pipeline. Nice piece Beth.


  2. July 29, 2015 at 9:30 pm, Mike Kunkle (@Mike_Kunkle) said:

    Nice job, Beth. Good to see you on the blog. I wrote a post recently about sales discovery skills and was surprised at the traction it got. It remains a relevant topic for many. I still see this as a gap in many sales forces, especially the lack of a strategic thought process to peel the onion and get past surface challenges to the impacts on both the business and the buyer(s), and the deeper needs.


    • July 14, 2017 at 8:54 am, Lorna said:

      Hi can you share the blog – I am interested for my tech service team. thanks L


  3. August 01, 2015 at 7:30 am, John Riordan said:

    A must read, is a book by Thomas Freese – Question Based Selling. It delivers a good diagnostic approach to successful selling. Tom discusses creating curiosity in the sales process to gain the customers interest, which creates mind share time with the customer.


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