The Best Open-Ended Questions for Salespeople to Ask

The Best Open-Ended Questions for Salespeople to Ask

If there’s one mistake Colleen Stanley has seen salespeople make over and over again in her 20-year career as a sales trainer, it’s a failure to ask the simple questions.

A well-timed follow-up like, “Can you give me a recent example?” may not shock anyone with its originality, but it does open the door for the customer to share a story. When that happens, the salesperson can gather the insight they need to build a relationship and close a deal.

Every salesperson knows that the key to effective discovery is to ask open-ended questions, but Stanley, who’s the president of SalesLeadership, has found that most forget to do it because they’re so focused on closing. She often encourages salespeople to make a list of these simple questions that they know they should ask but fail to, and then think about what information they’re missing out on.

The missing information could have helped them gain a deeper understanding of the customer’s issue, learn what their budget priorities are or establish an emotional connection. Without those, a deal isn’t likely to get done.

“An even more fun exercise is to have them imagine their competitor coming in and asking all of those simple questions,” Stanley said. “Who’s going to win the customer? The person who asked all the questions, that’s who.”

Ultimately, there is no shortcut to building rapport with a customer during discovery. Ask questions too quickly and it can make the customer feel like they’re being interrogated. Fail to ask a follow-up or interrupt them with a pitch, and you may miss out on valuable information.

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We spoke with Stanley, Anita Nielsen, who’s the author of the sales enablement book Beat the Bots and the founder of LDK Advisory, and Upwork sales trainer Alex Downey for their best open-ended questions and discovery tips.

  • Help me understand…
  • How does that impact you or your team?
  • Tell me about…
  • What does that mean for your career?
  • What’s not happening that you’d like to see happen?
  • Can you give me a recent example?
  • What’s making you take a closer look now?
  • What’s changed?
  • What else?
  • What would you do if…?

Anita Nielsen, President, LDK Advisory

In sales, you get told discovery is important, you know qualification is important, you get told ad nauseam that you have to use open-ended questions. But when you’re in your first meeting with a customer, your mind is not focusing on the types of questions you should be asking. Sales is high pressure and salespeople are taught to get to the ink, so they end up rushing the discovery process – and that’s a mistake. You’re leaving a lot of valuable information behind that you could have turned into additional sales opportunities. I’d say if you’re in an early meeting with a prospect and you start talking about your product any earlier than 45 minutes into it, that’s a mistake.

Help me understand.

This isn’t a question that you can ask right off the bat, but after they give you some information, it can be a great follow-up. The idea behind this type of question is that you want to get a lot of information, but you also want to get information that taps into emotion. If you ask a CIO, “Can you tell me about who reports to you?” that’s fine. But a high-impact question like, “Help me understand your organization structure?” is better. The first question will give you a list, whereas the “help me understand” questions leaves it open for the customer to respond with emotion and context that you can use to build a better relationship.