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Leading with Questions or Insights In Sales Calls: What’s the Right Strategy?

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Leveraging insights in sales calls is a very popular strategy in this age of the empowered customer. Our clients often ask us when in the sales conversation their sellers should lead with insight versus lead with questions.

The simple answer to this question is, “It depends.” I’ll provide some further guidance in this post, but I suggest you start by downloading our White Paper: Creating Trust With Buyers Through Selling With Insights and share it with your sales reps.

If you are up-skilling your sales team to sell with insight, there are a few important points to remember.

First, sharing insight is only one aspect of a sales conversation. Even if you have the most profound, mind-blowing insight, you will still need to prepare for the call, open the call, ask needs-related and solution-related questions, resolve objections, secure commitment, and then follow up. Insight sharing is an important skill, but it is not the only skill you will need for a successful call.

Second, understand the risk of sharing insight without careful thought and planning. The phrase “show up and throw up” used to apply to product pitching but has taken on a new life as sales reps try to jam in meaningless, irrelevant, self-serving grabbers. Nobody wants to be “that guy” who shows up, blows through his numbers play, and then gets shut down because his insight is superficial or irrelevant to the buyer. Preparation must also take into account what to do or what to say when a buyer pushes back on your insight. Resistance to new ideas is normal, and your sales reps need to be skilled to stay composed and work with the buyer to resolve the resistance.

Finally, keep in mind that your sales reps will typically be planning a single call and that not every call will result in a closed sale. You need to know where you are in your sales process and the buyer’s buying process. Then, you need to set reasonable objectives for your call based on where you are today and how far you think you can go, and you need a strategy for how you’re going to get from point A to point B. Insights and questions usually both play a role in achieving your call objectives.

All this said …

Lead with questions when:

  1. You don’t have a sufficient understanding of your buyer’s business,
  2. You require further understanding about their situation or attitude, or
  3. You seek their confirmation (checking) before moving forward in the conversation.
This includes:

  • Drilling deeper when the buyer has self-diagnosed a need
  • Understanding the buyer’s current thinking or point of view on an issue
  • Developing ideas together with the buyer
  • Checking that an issue leading to an insight is relevant
  • Gaining the buyer’s perspective on an important aspect of the sale
  • Developing opportunities resulting from insight sharing
Lead with insight when:

  1. You have a high level of familiarity with the buyer,
  2. You want to seed new ideas, or
  3. You want to influence his or her thinking.
This includes:

  • Triggering new ideas
  • Shaping the buyer’s current thinking
  • Differentiating yourself from your competition
  • Creating a sense of urgency
  • Building your credibility
  • Piquing your buyer’s curiosity
  • Disrupting your buyer’s current mindset
  • Overcoming bias or misconception
Jim Ninivaggi of Sirius Decisions sums it up well: “B2B selling still comes down to a series of conversations. Early in the sales process, your sales reps need to be provocative; in the middle, your reps need to build and prove differentiated value; and late in the process, they often have to elevate their conversation to the senior-most executive levels.”

Better prepared and more informed buyers means your people need new skills to bring more value to a customer conversation. Our complimentary white paper will help them better understand when to lead with insight versus lead with questions and make the maximum impact on buying influences.

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White Paper: Creating Trust With Buyers Through Selling with Insights


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