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Checklist: Challenger Sales Questions




Warm Up

  • Get to know the business 
  • Discover the solutions your prospect is considering 
  • Develop your talking points

“What problems are you facing?”

“What solutions are you considering?”


  • Show a new perspective 
  • Point out flaws in logic 
  • Highlight areas your prospect might be missing 

“A project management system is a great start, but it can only do so much. Have you considered how employee burnout could impact your scalability?”


  • Use emotions to build connections
  • Paint a picture of what could happen if they ignore your perspective 

“When your team burns out, you risk a dip in productivity, an unhealthy work environment, and losing top performers to new opportunities. All of these things can make scaling even harder.”

Imagine the Future

  • Sell the value proposition
  • Show what their life could look like with your product

“If you make your team’s job easier, you can do more in less time. You’ll reduce costs, improve productivity, and let your team focus on the work they love.”


  • Sell your product

“Automation software will not only make managing your projects easier, but it will take the repetitive and boring tasks off your team's plate. Scaling will become more efficient and sustainable.”