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The Art of Asking Better Questions

December 04, 20243 min read

Have you ever asked someone "Why did you do that?" and immediately sensed them becoming defensive? There's a good reason for that reaction, and it points to a crucial skill that many of us need to develop: the art of asking better questions.

The Problem with "Why"

Our brains are wired to react defensively to "why" questions. When someone asks us "why," it often feels like an accusation rather than a genuine inquiry. This triggering of our fight-or-flight response can shut down productive dialogue before it even begins.

Enter Calibrated Questions (*Term coined by Chris Voss of The Black Swan Group)

Calibrated questions represent a more sophisticated approach to information-gathering and problem-solving. These are thoughtfully crafted, open-ended questions that cannot be answered with a simple yes or no. But their power goes beyond just gathering information – they can actually help shape thinking and guide problem-solving processes.

The "What" and "How" Revolution

The most effective calibrated questions typically begin with "what" or "how." Consider these examples:

  • Instead of "Why aren't we meeting our goals?" try "What obstacles are you encountering in reaching these targets?"

  • Rather than "Why didn't this work?" ask "How do you envision this working more effectively?"

  • Instead of "Why did you choose this approach?" try "What factors influenced your decision-making process?"

These reformulated questions invite reflection and dialogue rather than defensiveness and justification.

The Strategic Impact

When we use calibrated questions effectively, we achieve several important objectives:

  1. We create psychological safety, allowing others to share their thoughts without feeling attacked

  2. We encourage deeper thinking and more detailed responses

  3. We empower others to participate in finding solutions

  4. We gather more accurate and useful information

The One Exception to the "Never Why" Rule

Interestingly, there is one strategic use for "why" questions: determining commitment levels early in a relationship or negotiation. The Black Swan Group calls this the "Proof of Life" question. For example, asking a potential client "Why did you choose to reach out to our company specifically?" can reveal whether you're their preferred choice or just one of many options they're considering.

Putting It Into Practice

To improve your questioning skills:

  1. Start paying attention to how often you use "why" questions and consciously replace them with "what" or "how"

  2. Practice formulating questions that require detailed responses

  3. Listen carefully to the quality of answers you receive – more detailed responses often indicate better questions

  4. Pay attention to your tone of voice – even well-crafted questions can be undermined by an accusatory tone

The Bottom Line

As Voltaire wisely noted, we should "judge a person by their questions rather than their answers." In our professional and personal lives, the ability to ask good questions is invaluable. By mastering the art of calibrated questioning, we can foster better communication, build stronger relationships, and achieve better outcomes in our interactions.

Remember: It's not just about asking questions – it's about asking the right questions in the right way.

Start practicing today, and watch how the quality of your conversations transforms.

At Journey To Legacy and the JTL Community, we focus on educational communications coaching to help you build stronger relationships and sell better. Join us and take your business and life to the next level, guaranteed.

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Wayne Veldsman

Wayne Veldsman, owner of Vel.Consulting and Journey To Legacy is an accomplished online business growth strategist, success coach, and entrepreneur. He specializes in helping global nonprofit organizations to change the world by helping them grow both their mindsets and their NPO's revenue. After starting his first business in 2014, Wayne successfully launched and scaled a digital marketing agency to a 7-figure valuation before deciding to exit in 2019 to move to Denver, Colorado and start chasing his passion of coaching and public speaking. Wayne actively works with executive directors, entrepreneurs and businesses who are looking to take massive action and create drastic changes in their lives.

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