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What Keeps You Up At Night?

Sales Training Article: Asking “What Keeps You Up At Night?”

By John Holland, Chief Content Officer, CustomerCentric Selling® – The Sales Training Company

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In considering selling issues, I’ve developed a healthy respect for the word context. The dictionary says it refers to surrounding conditions. A major barrier to achieving competence is the need for sellers to understand responses to buyers are highly dependent upon context.

sales training companiesDuring CustomerCentric Selling® workshops attendees ask many questions. Usually instructors have to clarify questions to make meaningful responses. The words “always” and “never” seldom apply to sales because there are few absolutes. Nearly every situation has different context.

A recent topic within the CustomerCentric Selling® LinkedIn community was whether asking executive buyers: “What keeps you up at night?” was good or bad technique. Let’s assume it’s an initial meeting and that you to ask in a less trite manner:

  • “What are you hoping to accomplish with (the offering being discussed)?”
  • “What business outcomes would you like to see?”

How well the question is received and whether the buyer provides a meaningful answer, or any answer at all, depends upon the context of the interactions leading up to it.

To expect a meaningful answer, a seller should earn the right to ask. This requires buyers to have made the decision that the seller is trustworthy. Steven Covey’s definition requires the buyer to believe the seller is:

  • Sincere – meaning rapport wasn’t forced and negative stereotypical behavior was avoided. The buyer feels the seller’s mission it to help rather than just sell something.
  • Competent – meaning there was a clearly stated objective and agenda for the call, an understanding of the buyer’s business landscape and an idea of how his or her offering relates to improving business results.

Forrester Research found the percentages of sales calls that met or exceeded expectations for IT and business executives were 13% and 11%, respectively. Ironically, executives meeting sellers probably have business issues that could be positively impacted by the vendor’s offerings. The reality is that executives won’t share them with sellers that fail the sincere and competent test.

Incompetent sellers try educating executives with details about their company and offerings. This approach falls on deaf ears because it’s just noise (content without context) for buyers. Regardless of how it’s phrased, “what keeps you up at night questions” are unlikely to warrant meaningful responses when this approach has been taken.

Competent sellers realize the first several minutes are about buyers and their organizations. The objective is the have buyers share one or more desired business outcomes. Discussing each allows conversations to include only the parts of offerings that are relevant to achieving those outcomes. This results in less noise and engaged buyers.

Learning context for executives and their organizations establishes competence and reduces the content about offerings that is shared. The Forrester study shows 7 out of 8 sellers struggle with this concept. Executive buyers deserve better.


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