Mastering the Art of Asking Questions and Building Confidence

Tara H

Hatched by Tara H

Sep 25, 2023

4 min read


Mastering the Art of Asking Questions and Building Confidence


Asking good questions is a skill that can unlock a world of knowledge and understanding. From Jerry Seinfeld's technique of using closed questions to Shawn Callahan's concept of story-eliciting questions, there are various approaches to uncovering the truth. Additionally, building self-confidence requires a different mindset, one that focuses on self-compassion rather than simply boosting self-esteem. In this article, we will explore the power of asking questions and how it intertwines with developing self-confidence.

The Art of Asking Good Questions:

Jerry Seinfeld, known for his comedic genius, offers valuable advice on asking questions. He suggests using closed questions that have numerical answers, as they prompt individuals to think deeply and share their thought process. By asking questions such as "How has it come to this?" or "What happened to you?", we can tap into a person's emotions, beliefs, and needs, fostering a deeper connection.

Story-Eliciting Questions:

Shawn Callahan, an executive coach specializing in business storytelling, introduces the concept of story-eliciting questions. Humans naturally think in narratives, and by asking "What happened?", we can delve into someone's personal experiences. This simple yet powerful question can be used to follow up on everyday statements and uncover compelling stories that provide valuable insights.

Chunking Down for Clarity:

Sometimes, our conversation partners provide general or abstract answers, assuming that the details are obvious. To tackle this, we can employ the technique of chunking down. By asking questions like "How does that fit into the larger picture?", we encourage individuals to provide more specific information. This method helps us gain a deeper understanding and avoid overlooking crucial details.

Calibrated Questions for Negotiation:

Former FBI hostage negotiator Chris Voss introduces the concept of calibrated questions. These questions begin with "how" and are tailored to the context of the situation. Calibrated questions put pressure on the counterpart to come up with answers and contemplate problems. Voss believes that these questions are invaluable in negotiations, as they keep the conversation flowing and ensure both parties remain engaged.

Columbo's Method: The Power of Persona:

The iconic detective Columbo, portrayed by Peter Falk, had a unique approach to questioning suspects. He made others feel "smarter than he was," creating an illusion that he had no ulterior motives. Columbo's signature move was the "one last thing.." question that he asked just when the suspects thought the interrogation was over. This technique caught them off guard and often led to crucial revelations.

Building Confidence through Self-Compassion:

Contrary to popular belief, building self-confidence does not solely rely on boosting self-esteem. Experts suggest that self-compassion is the key. Instead of focusing on the need for validation, self-compassion encourages individuals to try because they care about their well-being and do not wish to suffer. This mindset leads to genuine self-confidence, rooted in a deep understanding of one's worth.

Three Actionable Advice for Effective Questioning and Building Confidence:

  • 1. Practice active listening: When asking questions, it is crucial to actively listen to the responses. Pay attention to both verbal and non-verbal cues, allowing you to ask follow-up questions that delve deeper into the person's thoughts and emotions. This not only enhances your understanding but also shows genuine interest and builds rapport.
  • 2. Cultivate curiosity: Develop a genuine curiosity about the world and the people around you. Embrace a mindset that seeks to understand rather than judge. By approaching conversations with a genuine desire to learn, you create an environment where others feel comfortable sharing their experiences, fostering deeper connections and personal growth.
  • 3. Embrace self-compassion: Instead of striving for perfection and seeking external validation, focus on treating yourself with kindness and compassion. When faced with challenges, ask yourself, "What can I learn from this?" or "How can I grow through this experience?". By embracing self-compassion, you build resilience, learn from setbacks, and ultimately develop authentic self-confidence.


Asking good questions is a powerful tool for uncovering the truth and fostering deeper connections. Whether it's using closed questions, story-eliciting questions, or calibrated questions, each approach offers unique insights. Additionally, building self-confidence requires a shift in mindset, with self-compassion as the driving force. By incorporating active listening, cultivating curiosity, and embracing self-compassion, we can master the art of asking questions and develop genuine self-confidence. So, go forth, ask thought-provoking questions, and embrace the journey of personal growth and understanding.

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