The Art of Asking Better Questions: J.R. Briggs on Leadership and Connection

The Decline of Question Asking

• 🗣️ Conversational narcissism, fueled by social media and a culture that rushes to judgment over curiosity, is leading to a decline in meaningful conversation.
• 🍽️ The phenomenon of people not asking questions during extended interactions, dubbed "Waitress" by Briggs's wife, highlights a growing disconnect.
• 📱 The ubiquity of screens and the downstream effects of the pandemic have exacerbated this trend, contributing to an epidemic of loneliness.

The Power and Purpose of Questions

• 🧠 Asking questions, especially to oneself, is crucial for developing emotional intelligence (EQ) by fostering self-awareness and understanding others' perceptions.
• 💡 Jesus, despite his divine knowledge, asked over 300 questions, demonstrating their power for connection, transformation, and teaching.
• 🤝 Connection is the primary thing at stake when question-asking declines, impacting new ideas, creativity, and interpersonal relationships.

Obstacles to Asking Questions

• 🚧 Leaders often face the pressure of being the "answer person," hindering their ability to remain curious and ask questions.
• 📉 Exhaustion and acedia (spiritual torpor) can lead to a lack of effort and care, making it difficult to engage in thoughtful questioning.
• 💡 The trap of expertise and the fear of looking dumb or awkward prevent many from asking the questions that could lead to deeper understanding.
• ⏳ Questions can be perceived as inefficient in an efficiency-oriented world, leading to penalties in some professional environments.

The Art of Asking Better Questions

• 🌟 Peter Drucker emphasized the shift from leaders who tell to leaders who ask, highlighting the future leader as a question asker.
• 🤝 Younger generations prefer a "guide on the side" over a "sage on the stage," valuing leaders who walk alongside them and ask questions.
• ❓ "Dumb questions," as Drucker called them, are often the most valuable, pushing on assumptions and revealing what people haven't considered.
• 🎯 The motive behind a question is crucial: it should stem from a desire to learn and care, acting as an expression of hospitality.
• 💡 Jesus's questions often served as a scalpel, drawing blood to heal, demonstrating the potential for questions to bring about redemption.

Questioning in Communication and Leadership

• 🚀 Neuroscience shows that asking questions lights up the brain more than providing answers, temporarily hijacking attention and making listeners active participants.
• 🗣️ In preaching, employing Jesus's pedagogical methods—physical, emotional, and mental field trips—along with thoughtful questions, can increase engagement and transformation.
• ❓ Rhetorical questions, as used by Paul in Romans, can effectively set up arguments and engage the audience's thought process.
• 🎯 Leaders should aim for content, quality, frequency, and outward direction in their questions, moving beyond generic greetings to more engaging inquiries.
• 🤝 Curiosity is a powerful antidote to cynicism, and learning to ask better questions is a skill that can be cultivated through practice and awareness.

Practical Application of Question Asking

• ❓ Benevolent but useless questions like "What's up?" can be elevated by adding intentionality, e.g., "What's been the most interesting part of your day?"
• 🎯 Questions should be designed to be impossible to answer with one word, opening up conversations and encouraging deeper responses.
• 💡 Leading questions should be avoided in favor of guiding questions that invite exploration rather than dictating an answer.
• 🤝 When meeting influential people, asking for permission and coming prepared with thoughtful questions can lead to more meaningful interactions.
• 🎁 Asking questions that guests want to be asked, rather than the predictable FAQs, offers a gift of fresh perspective and engagement.
• 🤔 A key question to ask others is: "What is the question that people either don't ask you or don't ask you often that you wish they did?"