Enhance Your Listening Effectiveness with a Questioning Strategy

In a major study, the top 1% of sales reps were asked to identify what they felt was their most important sales skill. Over 60% of the respondents said listening! And the most effective listeners excel at a related skill: They ask great questions!


Importance of a Questioning Strategy

If you want to solicit information that will help you win, you need a strategy to take the conversation with your customer where it needs to go. What do you need to learn or validate to advance the sales process? A good questioning strategy combines a logical roadmap for this discussion with specific questions that create a great listening opportunity for you.

Diagnostic Questions

Every journalist knows they have to get information from the source and be able to validate it. To do this, they question more and talk less. In the same way, your most valuable sales calls can often be characterized by your customer doing most of the talking. A complete understanding of your customers’ needs requires asking diagnostic questions—the Who, What, When, Why, and How questions.


  • Who will perform the evaluation?

  • Whose operations will benefit the most?


  • What are you trying to accomplish?

  • What business problem are you trying to solve?


  • When will a decision be made?

  • When is the project to be completed?


  • Why is the company evaluating new approaches?

  • Why is this particular person on the evaluation team?


  • How do you measure the success of major investments?

  • How do you and your team manage major projects?

To ensure that you get your customer’s complete story, plan your questions. Regardless of how good you are, do not go into a call and wing it. Subtle changes in how an important question is constructed can make big differences in the quality of the response and where the conversation goes next.

Diagnostic Question Types

Questions come in many forms. How many of these are part of your questioning inventory?

Open vs. Closed: Open-ended questions are your ally in getting the complete understanding you need. Closed yes/no questions are useful in validating and gathering facts that may set up your next open-ended question.

  • Tell Me More -- "You mentioned concerns about xxx. Can you tell me more about that?"

  • Biggest / Smallest -- "The RFQ details six different criteria. In your opinion which would create the biggest improvement in your results?"

  • Best / Least -- "What aspects of our proposal do you like best? Least?"

  • Top Three -- "What are the top three features you are looking for in a solution?"

  • Magic Wand -- "If you could wave a magic wand and create the perfect supply chain partner, what would they look like?"

Fact vs. Feeling: While most salespeople are good at capturing the facts, the best salespeople are just as good as asking their customer what they think or how they feel about the situation. This is where a variety of probing questions comes in. Probing questions come in many forms.

Permission Question: If you want to shift the conversation to a new area that the customer may consider confidential or controversial, take five seconds to ask: "Is it OK if I ask a few questions about xxx?" Failure to do so, particularly in some cultures, can shut the conversation down.

Catch All: Get in the habit as you are summarizing the call to ask, "Is there anything else relating to xxx that you want to mention?" Do not be surprised when you open a door to a new opportunity you were unaware of.

Diagnostic Questioning Strategy

So you have your call objective and a number of good questions to use to drive the conversation. These three best practices will help you build a logical roadmap for the conversation.

1. Start high level. It is important to start the conversation at a high level. Otherwise you could head into the weeds without realizing that things may not be as they appear. Start on non-controversial areas heavy on facts. Get your customer in the mode where they are doing the talking and explaining. At this stage a lot of the conversation is centered on the current state.

2. Merge into feelings. Once your customer is fully engaged, listen for an opportunity to interject a probing question: “"What do you think about that?" Continue to drill down utilizing restatement and follow-up questions, particularly if this relates to pains and problems with your customer’s current situation. Let them get it all out. Resist the temptation to assume you understand: peel the onion slowly, one layer at a time. A catch-all question like "Anything else about your current situation..?" could validate it’s time to move on.

3. Transition to the desired state. You may use a permission question to signal the transition: "Are you ready to talk about the solution that would be right for you?" You will probably start with some fact-gathering questions. What you learned thus far though prepares you to interject probing questions much more quickly.

Pair fact-gathering questions with probing questions to solicit your customer’s opinions and feelings. You can usually assume your competitors will capture facts similar to yours. The insight you gather in getting beyond the facts is what can differentiate your solution as the best fit. There is more to align your value to than facts printed on the RFP.

Don’t forget to use that catch-all question at the end: "What else should we have talked about? What should I have asked you but didn’t?” Try doing this every time and you will be rewarded with insight you would have otherwise missed.

Top sales performers are great listeners. The very best listening opportunities come from asking great questions. You have three options in call preparation:

  1. Go in and wing it.

  2. Plan compelling diagnostic questions.

  3. Develop a questioning strategy that combines compelling questions in a logical roadmap.

Which one are you going to choose?