Customer Experience News & Trends

The worst question you can ask customers

This one question is probably asked by more salespeople in a given day than any other. It’s a question that may simultaneously prevent sales and destroy customer loyalty. 

The question: “What’s keeping you up at night?”

How it started

For years, salespeople were told that the shortest path to sales success is a deep understanding of customer needs. If salespeople can understand what’s keeping customers up at night, they can build tight linkages between customer problems and the products or services they’re selling.

This approach leads to two major problems:

  1. It’s difficult for salespeople to come up with immediate solutions in response to the question.
  2. The question assumes that customers actually know what it is that should be disturbing their sleep.

What if customers don’t know what they need? What if their single greatest need is to figure out exactly what they need?

Customers who are in the dark about their actual needs may be turned off by a question they can’t answer.

Relationship builders

Salespeople who ask questions like “what’s keeping you up at night?” are called “relationship builders.” They are all about nurturing strong personal and professional relationships, they are very generous with their time and they work hard to ensure that customers’ needs are met.

Their primary posture with customers is largely one of accessibility and service. “Whatever you need, I’m here to make that happen” is the message they deliver to customers. They let the customer take the lead, adopting a service mentality.

A recent survey by the Corporate Executive Board’s Sales Executive Council of 1,000 customers asked them to rate what they valued most in salespeople.

Less than 3% of the respondents even mentioned relationships. An overwhelming majority listed qualities the Corporate Executive Board identified as belonging to a “challenger salesperson.”

The challenger salesperson

Instead of asking prospects what’s keeping them up at night, challenger salespeople tell prospects what should be keeping them up at night. They have a deep understanding of the prospect’s business and use that knowledge to challenge prospect thinking and teach prospects something new about how their companies operate.

No fear

Challengers are not afraid to share their views, even if they’re different and potentially controversial. They’re constantly bringing fresh insight to their customers and the mangers within customers’ companies.

They lead and simplify. Challengers excel at teaching, tailoring and taking control. They are focused on pushing customers out of their comfort zone.

Made not born

A challenger is defined by the ability to teach, tailor and take control — three things that any motivated salesperson can do.

There are many sources of information that can help salespeople tailor their approach to customers.


  • Industry trends
  • Current events
  • Industry mergers
  • Competitor struggles and
  • Competitor’s market share fluctuations.

Taking control of the sale

Challengers have an ability to assert and maintain control over the sale. Being assertive doesn’t mean being overly aggressive, annoying or abusive. It’s all about a salesperson’s ability and willingness to stand firm when the customer begins to push back.

Challenger salespeople arrive at a presentation with a deep understanding of the prospect’s concerns, as well as the specific results he or she wants to achieve. They aren’t focused on what they’re selling but on what the prospect is trying to accomplish.

They are able to pressure the customer’s decision-making cycle to overcome indecision and help them make decisions more quickly.

They move customers out of their comfort zone by showing them their world in a different light — and they do it with control, diplomacy and empathy.

What customers want

Surveys of customers consistently show that they put the highest value on salespeople who make them think, who bring new ideas to the forefront and who find creative and innovative ways to help their businesses.

Customers now demand more depth and expertise. They expect salespeople to teach them things they don’t now. These are the core skills of challenger salespeople. They are the sales skills of the future.

Adapted from: “The Challenger Sale,” by Matthew Dixon and Brent Adamson. Dixon is a manager director and Adamson is a senior director with the Corporate Executive Board’s Sales Executive Council in Washington, D.C. The Corporate Executive Board offers unique research insights along with an integrated tools and resources.

Subscribe Today

Get the latest customer experience news and insights delivered to your inbox.