20 Questions

Questions to Ask Your Role Model

Meaningful questions to ask your role model to learn from their experiences, gain wisdom, and understand the path that led to their success.

1

What was the most significant turning point in your life and how did it change you?

Click to see why this works

Why this works

Reveals the pivotal moments that shaped their character and success, providing insight into how major life events can transform a person.

2

What advice would you give to your younger self at my age?

Click to see why this works

Why this works

Provides valuable guidance tailored to your current life stage, offering wisdom they wish they had known earlier.

3

What has been your biggest failure and what did you learn from it?

Click to see why this works

Why this works

Shows their vulnerability and resilience, demonstrating how setbacks can become valuable learning experiences.

4

How do you approach making difficult decisions, especially when the stakes are high?

Click to see why this works

Why this works

Reveals their decision-making process and provides a framework you can apply to your own challenging choices.

5

What habits or practices have been most important to your success?

Click to see why this works

Why this works

Identifies specific behaviors and routines that contributed to their achievements, giving you actionable strategies to implement.

6

How do you handle setbacks and maintain motivation during difficult times?

Click to see why this works

Why this works

Provides insight into their resilience and coping strategies, helping you develop your own approach to overcoming challenges.

7

What do you wish you had known earlier in your career or life?

Click to see why this works

Why this works

Reveals knowledge gaps they experienced and provides guidance on what to focus on for your own development.

8

How do you balance your personal and professional life?

Click to see why this works

Why this works

Shows their approach to work-life balance and provides strategies for maintaining relationships while pursuing goals.

9

What has been your most rewarding achievement and why does it matter to you?

Click to see why this works

Why this works

Reveals their values and what they consider truly meaningful, helping you understand what success looks like to them.

10

How do you continue to grow and learn, even after achieving success?

Click to see why this works

Why this works

Demonstrates their commitment to lifelong learning and provides insight into how to maintain growth mindset.

11

What role has mentorship played in your own development?

Click to see why this works

Why this works

Shows the importance of guidance and relationships in their journey, encouraging you to seek out your own mentors.

12

How do you approach taking risks and stepping outside your comfort zone?

Click to see why this works

Why this works

Reveals their relationship with risk and provides strategies for embracing uncertainty and growth opportunities.

13

What values guide your decisions and how have they evolved over time?

Click to see why this works

Why this works

Shows their moral compass and how their principles have shaped their choices and relationships.

14

How do you handle criticism and feedback, especially when it's difficult to hear?

Click to see why this works

Why this works

Demonstrates their approach to growth and learning from others, providing strategies for handling constructive criticism.

15

What has been your approach to building and maintaining relationships?

Click to see why this works

Why this works

Reveals their relationship philosophy and provides insight into how to cultivate meaningful connections.

16

How do you stay focused on your goals while remaining open to new opportunities?

Click to see why this works

Why this works

Shows their approach to goal-setting and flexibility, providing strategies for maintaining direction while staying adaptable.

17

What do you think are the most important qualities for success in your field?

Click to see why this works

Why this works

Provides specific guidance on what skills and characteristics are most valuable in their area of expertise.

18

How do you approach giving back and making a positive impact on others?

Click to see why this works

Why this works

Reveals their values around service and contribution, inspiring you to consider your own impact on the world.

19

What would you do differently if you could start over?

Click to see why this works

Why this works

Provides insight into their regrets and lessons learned, offering guidance on what to prioritize in your own journey.

20

How do you define success and has that definition changed over time?

Click to see why this works

Why this works

Reveals their evolving understanding of success and provides perspective on what truly matters in life.

Learning from Role Models

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

Effective Role Model Conversations

Show Genuine Respect

Approach the conversation with authentic admiration and curiosity about their journey and experiences.

Ask About Their Process

Focus on how they achieved their success, not just what they accomplished. Understanding their methods is more valuable than hearing about their results.

Listen for Wisdom

Pay attention to the deeper insights and life lessons they share, not just the surface-level advice.

Key Areas to Explore

Life turning points and pivotal moments
Advice for your current life stage
Failures and lessons learned
Decision-making processes
Success habits and practices
Resilience and motivation
Work-life balance
Values and principles
Relationship building
Continuous learning and growth

Common Mistakes to Avoid

Don't Put Them on a Pedestal

Remember they are human with flaws and struggles. Don't idealize them to the point where you can't learn from their mistakes.

Don't Ask for Specific Career Advice

Focus on general principles and life lessons rather than asking them to solve your specific problems or make decisions for you.

Don't Ignore Their Humanity

Ask about their struggles and failures, not just their successes. Their challenges are often more instructive than their victories.

Conversation Frameworks

The Wisdom Seeker

1
Step 1: Start with: 'What advice would you give to your younger self?'
2
Step 2: Follow with: 'What do you wish you had known earlier?'
3
Step 3: Deepen with: 'What would you do differently if you could start over?'

The Process Explorer

1
Step 1: Begin with: 'How do you approach [specific challenge]?'
2
Step 2: Continue with: 'What has been your biggest failure and what did you learn?'
3
Step 3: Explore with: 'How do you handle setbacks and maintain motivation?'

Further Reading

"The Mentor's Guide" by Lois J. Zachary
"The Power of Mentorship" by John C. Maxwell
"Finding Your Own North Star" by Martha Beck

Find Your Perfect Questions

Search our collection of thoughtful questions for any conversation or situation