Most people are terrible at asking questions. Here's how to fix it

Philipp HummAbout 2 min readAug 15, 2025Watch original
THE SUMMARYAI-generated

Key Concepts:

  • Active Listening vs. Passive Questioning
  • Clarifying Questions
  • Emotional Connection
  • Feeling Seen vs. Feeling Scanned

The Problem: Rapid-Fire Interview Style Questioning

The speaker recounts a negative experience with a former colleague during a coffee meeting. Initially, the conversation seemed positive as the colleague asked standard questions about the speaker's life ("What did you do at your parents' place?", "How's work?", "Still living in Amsterdam? Any trips planned soon?"). However, the speaker quickly realized that the interaction felt like a "rapid-fire interview" with no genuine interest or follow-up. The speaker felt that the colleague "doesn't really care about me." The speaker posits that the colleague likely believed he was being a good listener, highlighting the disconnect between perceived and actual listening skills.

The Solution: Asking Clarifying Questions for Deeper Engagement

The speaker advocates for a different approach: asking clarifying questions to foster deeper engagement and make people feel seen. Instead of simply moving on to the next question, the speaker suggests pausing and asking questions that explore the other person's experience and emotions.

Examples of Clarifying Questions:

  • "Wait, what was that like for you?" - This question encourages the speaker to elaborate on their experience and share their perspective.
  • "That sounds intense, like tell me what happened." - This question invites the speaker to provide more details about a specific event.
  • "How did you feel in that moment when that happened?" - This question focuses on the speaker's emotional response, creating a deeper connection.

The Impact: Feeling Seen vs. Feeling Scanned

The speaker emphasizes that asking clarifying questions is crucial for making people feel "seen" rather than "scanned." By showing genuine interest in the other person's experiences and emotions, you create a more meaningful and authentic connection.

Synthesis/Conclusion:

The key takeaway is that effective listening goes beyond simply asking questions. It involves actively engaging with the other person's responses, asking clarifying questions to delve deeper into their experiences and emotions, and making them feel truly seen and understood. Avoiding a rapid-fire, interview-style approach and instead focusing on genuine curiosity and empathy is essential for building strong relationships.

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