Nine Provocative Questions That Create Winning Conversations

Are You Asking the Right Questions?

Asking every client the same 20 diagnostic or assessment questions is a comfort zone approach that has been taught for the past 30 years. However, it does nothing to add value to your customer conversations or differentiate you from your competition.

This is especially true if you’re asking the exact same 20 questions your competitors are asking, which practically ensures that you’ll disappear into the competitive field.

The solution? Ask provocative questions in your customer conversations.

Unlike the traditional diagnostic approach, provocative questions are not requests for data that customers already know. Instead, they provoke a different way of thinking and can demonstrate genuine interest and authentic curiosity. One or two well-placed provocative questions are enough to ignite an entirely new conversation.

To help you get started using these in your customer conversations, I’ve provided three categories of provocative questions below. Use these to jump-start your process for creating questions that differentiate you from the competition, open the door to unique customer insights and position you to move this deal forward toward a win.

Category #1: Yes/No Questions

  • Can be answered with “yes,” “no,” or some variation of “Why do you ask?”
  • Create productive dialogue.
  • Introduce a new topic.


  1. “So would you agree that…?”
  2. “Is this the kind of project that people will…?”
  3. “Are you prepared for…?”
  4. “Is your division ready to…?”

Category #2: Third-Party Data Questions

  • Prompt the customer to respond to a provocative piece of data that shifts the discussion to a topic related to your value.
  • Get the customer to take a position on a challenging subject related to the data and how they are responding today.
  • Cite the customer’s press releases or annual report, a piece of information from an industry journal, or data from your own company’s experience.


  1. “I noticed on your website that your CEO is now talking a lot about _____. How is that likely to affect the implementation of the project we’re discussing?”
  2. “There was an article in Bloomberg Businessweek last month that suggested that more than half of all IT directors plan to implement projects to address _____. How is your company dealing with this challenge?”

Category #3: Prioritizing or Comparing Questions

  • Challenge the customer to prioritize or compare things in ways that highlight areas where you might add value.
  • Get the customer to take information that is already in their head and view it in new or unusual ways.
  • Lead the customer to think of things they have not thought of before and expand the potential scope of the opportunity.


  1. “If you had the power to implement this project in its ideal form, what would it look like?”
  2. “You’ve told me the four criteria you have for moving forward with this project. Could you prioritize those criteria for me, and assign a relative weight to each one?”
  3. “Compare for me how the issues driving this purchase are the same as, or different from, the ones we addressed at the end of last year.”

As you put your list together, keep in mind that provocative questions aren’t simply intended to create a more interesting, memorable conversation. Instead, well-crafted provocative questions create demand for the solution you have to offer by delving deeper into your customer’s known and unconsidered needs. As the conversation progresses, you’ll show how your solution lines up to meet these needs, planting the seed for a conversation that wins the deal.

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