Ask the Right Questions

The Most Powerful Method to Develop Self-Awareness for All Leaders

Tim Hagen
March 17, 2025 • Estimated Reading Time: 5 minutes

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In this issue…

Ask the Right Questions: The Most Powerful Method to Develop Self-Awareness for All Leaders
Extra Insights- What Makes a Leader Great (Simon Sinek)
Weekly Motivation Boost - I’m Going to Win
Action for the Week - 3 things to encourage positivity around you
Together with Deel - An International Hiring Guide

🎯 EXPERT OF THE WEEK

📰 Ask the Right Questions: The Most Powerful Method to Develop Self-Awareness for All Leaders

From Tim Hagen

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Self-awareness is the foundation of personal and professional growth. It allows individuals to recognize their strengths, identify areas for improvement and navigate challenges with confidence. But how do we cultivate self-awareness?

The most powerful method is simple: ask questions. By asking the right questions, we encourage reflection, uncover blind spots and open the door to meaningful self-improvement. Below are 10 self-awareness-driven questions categorized into two key areas: performance and collaboration & communication.

Self-Awareness Questions for Performance

What do you consider to be your greatest accomplishment in the past year? Why?
What aspects of your current role do you find most challenging, and how do you usually address them?
What specific feedback have you received recently that resonated with you the most? Why?
What are your key strengths that you believe contribute most to the team’s success?
What areas of your work do you feel you could improve to be more effective?

Self-Awareness Questions for Communication & Collaboration

What strategies do you use to effectively communicate with colleagues who have different communication styles?
What role do you typically play in team meetings and discussions? Why do you play that particular role?
What is your preferred method of receiving feedback? Why?
What challenges have you faced when collaborating with others, and how do you overcome them?
What do you believe are the key components of a successful team?

The Power of “What” Questions

When asking self-awareness questions, word choice matters. Instead of asking these questions with negative word connotations:

🚫 Why aren’t you more collaborative?

🚫 Why are you struggling with performance?

Reframe with "What" questions that invite constructive reflection with more positive connotations:

✅ What strategies could help you become more collaborative?

✅ What steps can you take to improve your performance?

"Why" questions often put people on the defensive, making them feel judged rather than encouraged. Thoughtfully structured questions encourage honest, transparent and authentic conversations.

Plan Your Questions, Drive Self-Awareness

Self-awareness doesn’t happen by accident—it’s cultivated through intentional reflection and questioning. When we guide ourselves and others through this process, we create a more engaged, effective and cohesive team. Ask the right questions. Create self-awareness. Build better teams.

💡EXTRA INSIGHTS

What Makes a Leader Great - from Simon Sinek

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