20 Questions

Questions to Ask Your Hero

Meaningful questions to ask someone you admire, helping you learn from their experiences while showing genuine respect for their journey and wisdom.

1

What has been the most defining moment in your life?

Click to see why this works

Why this works

Reveals the pivotal experiences that shaped them and provides insight into the events that had the greatest impact on their character and direction.

2

What advice would you give to your younger self?

Click to see why this works

Why this works

Shows their wisdom and self-reflection while providing valuable insights that can help others avoid mistakes and make better decisions.

3

How do you stay motivated during difficult times?

Click to see why this works

Why this works

Reveals their resilience strategies and provides practical advice for maintaining motivation and hope during challenging periods.

4

What's something you've learned that changed your perspective on life?

Click to see why this works

Why this works

Shows their growth and evolution while providing valuable insights that can help others expand their own understanding.

5

How do you handle failure and setbacks?

Click to see why this works

Why this works

Reveals their approach to adversity and provides valuable lessons about resilience, learning from mistakes, and moving forward.

6

What values are most important to you and why?

Click to see why this works

Why this works

Shows their core beliefs and principles while providing insight into what guides their decisions and actions.

7

How do you approach making difficult decisions?

Click to see why this works

Why this works

Reveals their decision-making process and provides valuable insights into their approach to complex choices and trade-offs.

8

What's something you're still working on improving about yourself?

Click to see why this works

Why this works

Shows their humility and ongoing commitment to growth while making them more relatable and human.

9

How do you balance your personal and professional life?

Click to see why this works

Why this works

Reveals their approach to work-life balance and provides practical advice for managing competing priorities and responsibilities.

10

What's the most important lesson you've learned from your experiences?

Click to see why this works

Why this works

Shows their wisdom and provides valuable insights that can help others learn from their experiences and avoid common pitfalls.

11

How do you handle criticism and negative feedback?

Click to see why this works

Why this works

Reveals their resilience and provides valuable lessons about maintaining confidence and learning from feedback.

12

What's something you wish you had known earlier in life?

Click to see why this works

Why this works

Provides valuable hindsight that can help others make better decisions and avoid common mistakes.

13

How do you approach learning and personal development?

Click to see why this works

Why this works

Reveals their commitment to growth and provides valuable insights into their approach to continuous learning and self-improvement.

14

What's something you're proud of that might not be obvious to others?

Click to see why this works

Why this works

Reveals hidden achievements and provides insight into what they value most, beyond what's publicly recognized.

15

How do you handle stress and maintain your mental health?

Click to see why this works

Why this works

Shows their self-care strategies and provides valuable advice for managing stress and maintaining well-being.

16

What's something you've changed your mind about over time?

Click to see why this works

Why this works

Shows their growth and adaptability while providing valuable lessons about being open to new perspectives and changing one's mind.

17

How do you approach building and maintaining relationships?

Click to see why this works

Why this works

Reveals their approach to human connections and provides valuable insights into their philosophy of relationships and community.

18

What's your philosophy on success and what it means to you?

Click to see why this works

Why this works

Shows their definition of success and provides insight into what they value most in life and work.

19

How do you approach giving back or helping others?

Click to see why this works

Why this works

Reveals their values around service and community while providing insight into their approach to making a positive impact.

20

What's something you're looking forward to in the future?

Click to see why this works

Why this works

Shows their optimism and forward-thinking while providing insight into their goals and aspirations for the future.

Best Practices for Talking to Your Hero

Expert tips and techniques for getting the most out of these questions.

Best Practices

Show Genuine Respect and Appreciation

Express your admiration authentically and show that you value their time and wisdom. Be specific about what you admire about them.

Listen Actively and Show Interest

Pay close attention to their responses and ask follow-up questions that show you're genuinely engaged with their answers.

Be Humble and Open to Learning

Approach the conversation with humility and a genuine desire to learn from their experiences and wisdom.

Conversation Starters

The Wisdom Seeker

1
What has been the most defining moment in your life?
2
What advice would you give to your younger self?
3
What's the most important lesson you've learned from your experiences?
4
What's something you wish you had known earlier in life?

The Growth Explorer

1
How do you handle failure and setbacks?
2
What's something you've learned that changed your perspective on life?
3
What's something you're still working on improving about yourself?
4
What's something you've changed your mind about over time?

Common Pitfalls

Don't Put Them on a Pedestal

Remember they're human too. Avoid treating them as perfect or infallible, as this can make them uncomfortable and limit authentic conversation.

Avoid Overwhelming Them

Don't ask too many questions at once or make the conversation feel like an interview. Give them space to share naturally.

Don't Focus Only on Their Achievements

Ask about their struggles, failures, and personal growth too. This makes them more relatable and provides more valuable insights.

Conversation Templates

The Wisdom Exchange

1
Step 1: Start with: "What has been the most defining moment in your life?"
2
Step 2: Follow with: "What advice would you give to your younger self?"
3
Step 3: Explore with: "What's the most important lesson you've learned?"

The Growth Conversation

1
Step 1: Begin with: "How do you handle failure and setbacks?"
2
Step 2: Probe with: "What's something you're still working on improving?"
3
Step 3: Connect with: "What's something you've changed your mind about?"

Further Reading

"The Hero's Journey" by Joseph Campbell
"Mentoring 101" by John C. Maxwell
"The Power of Vulnerability" by Brené Brown

Find Your Perfect Questions

Search our collection of thoughtful questions for any conversation or situation