Skill 01.15: Questioning

Written on 07/04/2025
Tiffany Andras

Strategic questioning facilitates clarity, critical thinking, and engagement in meaningful dialogue.

Leaders who ask thoughtful questions encourage problem-solving, gather valuable insights, and challenge assumptions. This skill fosters innovation, strengthens communication, and promotes a culture of continuous learning and curiosity.

Practical Exercise: The “Ask 3 Deep” Method

In your next conversation, practice deepening understanding by asking three levels of questions:

  1. First Question – Surface Level → Start with a broad, open-ended question.

    • Example: “What challenges are you facing with this project?”

  2. Second Question – Dig Deeper → Seek more insight by exploring their response.

    • Example: “What do you think is the main cause of this challenge?”

  3. Third Question – Challenge Assumptions → Encourage critical thinking and new perspectives.

    • Example: “If you approached it differently, what might change?”

Action Step: In your next conversation, use the Ask 3 Deep method to encourage deeper dialogue and uncover valuable insights.