Questions are the key to pricing power.  I’ve written innumerable blog posts and recorded countless videos about this critical selling skill.  Each time I beat the drum, I include a few example questions that help me make the point essential to the blog or video.  At long last, I’m gathering some of the questions from past published content in one place for easy reference.  What’s your favorite question?

Casey’s Favorite Question

“Beyond price, what matters to you as you make this decision?”

• Alternate version: ”If everyone’s prices were identical, who would you choose?  Why?”
• Bonus question: “Tell me more.”  (Ok, it’s not technically a question, but it’s magic for pulling out key information.  Ask this a bunch. Not just after you ask what they value beyond price.  Ask this after every answer they give.  Ok, not every answer.  But ask this a bunch.  You will not believe what you learn when you ask them for more clarity, detail, or understanding.)

Visioning Questions

1. “If we sat down one year from today, and you were thrilled with how this turned out, what specifically would have happened?”
2. “What would hitting a home run on this project enable your team or company to do next?”
3. “What outcome would truly set you apart from your competition or help you grow faster than you thought possible?”
4. “Fast forward to the end of next quarter: what specific results or outcomes would tell you this was the best decision you’ve made all year?”
5. “If you could wave a magic wand, what’s the one thing you’d love to see transform in your business as a result of partnering with us?”
6. “Describe the ideal scenario for how our solution helps you achieve something important, whether that’s profitability, growth, efficiency, or something else.”
7. “Imagine telling a colleague about this solution a month from now. What would you want to be able to proudly share about your results?”
8. “What does absolute success look like for your customers when they interact with your business after implementing our solution?”

Questions to Uncover Needs

1. “What’s the one thing no one ever seems to understand about your business, but which, if understood, could completely change how providers work with you?”
2. “When you look at your top-performing vendors or partners, what exactly are they doing that you wish everyone else would?”
3. “If price wasn’t part of the conversation, what’s the number one thing you’d base your decision on?”
4. “What’s the hidden risk or cost in your business that keeps sneaking up on you… something that most suppliers don’t even think about?”
5. “When things go exceptionally well with a partner, what specifically are they doing differently to make your life easier or better?”
6. “What problem, if we solved it together, would significantly change how your business operates or performs?”
7. “What’s the one issue that keeps resurfacing no matter what solutions you’ve tried so far?”
8. “In your experience, what’s the biggest gap between what vendors promise and what they actually deliver?”

Questions to Probe for Past Pain Points

1. “Share an experience when slow or inadequate customer support negatively impacted your team’s productivity or results. What were the consequences?”
2. “Talk me through an experience where complexity caused frustration or delays. How did that affect you?”
3. “Tell me about a time when a supplier dropped the ball. How did that impact your team? Your customers? Your peace of mind?”
4. “Describe a situation when a lower-quality solution created significant problems or disruptions for you. What happened next?”
5. “Tell me about a scenario when a provider’s lack of expertise created risks or challenges for your business. What were the outcomes?”
6. “Describe instances where unexpected fees or hidden costs hurt your budget. How would transparency and predictability have changed the outcome?”
7. “Tell me about a time when delivery speed made or broke a deal for you. How did that play out, and what impact did it have?”
8. “Tell me about a past purchase decision like this that didn’t go well. What lessons are you carrying forward?”

Other Questions

1. “What criteria or factors are you evaluating that you haven’t mentioned yet?”
2. “Why are we talking about this now instead of, say, six months from now?”
3. “What are the biggest hurdles you anticipate internally as you make this decision?”
4. “What else are you considering right now, and how are you weighing your options?”
5. “What happens if you decide to hold off or do nothing?”
6. “Who in your organization will be most impacted by the success or failure of this decision?”
7. “Tell me about the different perspectives you’re managing internally. What do others in your organization care most about regarding this decision?”
8. “What does success on this project mean for you?”