The Most Powerful Questions In Sales

When dealing with senior executives, never use any form of manipulation. Instead allow them to feel in control and build trust through the way you engage and create understanding with the insightful questions you ask.

Outdated hook and tie-down questions are to be avoided with those in the executive suite at all times. Examples of these credibility destroying behaviors include: ‘If I could show you how to improve your bottom line, is that something you would be interested in?’ or ‘If I can demonstrate that we can meet that requirement, would you be willing to buy from us?’ These types of questions are closed and manipulative – don't do it when engaging at the most senior levels.

People are best convinced for reasons they themselves discover. Although there is a role for insight or Challenger selling for earning credibility, never forget that ‘telling is not selling’. Here are some powerful questions for C-level interactions that you may wish to adapt for your own purposes:

• I’ve done my homework but there are some questions I think only you can answer – may we cover a few of these now?
• What is really driving the need to make this kind of investment?
• What has to be delivered in terms of business outcomes?
• Where do you see the risks?
• Who are the most senior people affected by this project; and how will they be impacted and what’s their role in implementing a solution?
• What is your process and timing for making a decision and having 
a solution in place?
• What are the other options you’re considering? Why are these attractive?
• If we do business together, it is important for me to understand 
exactly what will make you 100% satisfied. What needs to happen 
for this business relationship to be successful in your eyes?
• The meeting today has been very useful, what would you like 
me to do next?
• You are very busy and have many people seeking meetings with you, so why did you agree to meet with me today?


Questions possess amazing power. The right question at the right time can create doubt, interest, support, self-reflection, decision or action. Plan every meeting and interaction; especially focus on planning the questions you will ask. Anticipate where the questions will take the conversation and go beyond the obvious of asking open questions instead of closed. Choose your questions wisely as they say much about who you are and how far the relationship is likely to go. Finally, focus on the why and when, rather than on the what and how.

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Photo by: Nana B Agyei