Questions About Life Experiences: Guide to Ask & Tell

Why Questions Shape Our Stories

Everyone has a story. The problem is, we don’t always know how to tell it—or how to ask the right questions to unlock it.

Maybe you’ve sat across from a friend, a parent, or even yourself, wondering what to say. You want to go beyond the usual small talk, past the surface-level details, and into the good stuff—the memories, the turning points, the struggles that shaped someone’s life.

But where do you start?

Life is a collection of moments, choices, and lessons, but we rarely pause to reflect on them. Whether you’re looking to deepen personal relationships, explore your own journey, or interview someone for their life story, asking great questions is the key to personal growth and understanding.

This guide is filled with life interview questions, self-reflection prompts, and conversation starters that can help you uncover valuable insights—both in your own life and in the stories of others.

So, grab a notebook, open your mind, and get ready to ask (and answer) the questions that matter.

1. Why Asking Questions About Life Experiences Matters

Human beings are natural storytellers. It’s how we process the world, make sense of pivotal moments, and connect with one another.

Think about the last time you had a truly deep conversation. Maybe it was with a family member, an old friend, or even a stranger. What made it memorable? Chances are, it wasn’t just what they said—it was the way they revealed something personal, unexpected, or profound.

Asking the Right Questions Helps Us:

✅ Learn from Past Experiences – By asking about childhood memories or major changes, we can see how challenges shape who we become.

✅ Build Meaningful Relationships – Understanding someone’s career path, personal interests, or life purpose deepens our connections.

✅ Discover New Perspectives – Everyone sees the world differently. Asking about work-life balance, professional development, or leadership roles can give us fresh insights.

✅ Reflect on Our Own Growth – Sometimes, asking others about their journey helps us see where we’re headed.

We ask questions every day, but are we asking the ones that truly matter?

2. The Art of Asking Good Questions

Not all questions are created equal. Some lead to deep conversations, while others fall flat.

A good question is like an open door—it invites the other person to step through and explore their thoughts. A bad question? It’s a dead end.

What Makes a Question Powerful?

    •    It’s Open-Ended: Instead of “Did you like your job?”, ask “What did your first job teach you about life?”

    •    It Encourages Reflection: Instead of “Was college hard?”, ask “What was the most crucial element in your education?”

    •    It Digs Into Emotion: Instead of “Did you have a good childhood?”, ask “What’s a memory from your childhood that still shapes you today?”

Great questions don’t just gather facts—they uncover stories.

Examples of Deep Questions That Spark Life Stories:

    •    “What was a turning point in your life that changed everything?”

    •    “What’s the biggest lesson your younger self needed to hear?”

    •    “How did a major change in your life shape your work ethic?”

    •    “What’s a moment you wish you could relive, and why?”

Follow-up questions are just as important as the initial ones. When someone shares a story, ask:

🔹 “What happened next?”

🔹 “How did that make you feel?”

🔹 “Did that experience change your future plans?”

The goal is to create a conversation that flows naturally—not an interrogation, but a discovery process.

3. Questions to Ask Yourself for Self-Reflection

Before we start asking others about their experiences, we need to turn the mirror inward.

Self-reflection is one of the most underrated tools for personal growth. By asking ourselves the right questions, we gain clarity about our past, our present, and where we’re headed.

Self-Reflection Questions for Personal Development:

    •    “What childhood experiences shaped the person I am today?”

    •    “What’s my favorite thing about my personal life right now?”

    •    “When was the last time I stepped out of my comfort zone?”

    •    “What’s a decision I made that completely changed my future?”

    •    “What’s one thing I’d tell my younger self?”

How to Use Self-Reflection for Growth:

    •    Write It Down: Journaling helps solidify your thoughts.

    •    Talk About It: Share your answers with a trusted friend or mentor.

    •    Take Action: If a question reveals a gap in your life, explore ways to fill it.

The better you understand your own story, the more you can appreciate the stories of others.

4. Questions to Ask Family Members About Their Life Stories

Family stories hold a unique kind of wisdom. Understanding where we come from can give us insight into our core values, work ethic, and personal relationships.

But family conversations often stay at the surface. How do we go deeper?

Great Questions to Ask Parents or Grandparents:

    •    “What was the biggest challenge you faced in your younger years?”

    •    “What was a great way your family celebrated holidays?”

    •    “What’s one lesson you learned about love and relationships?”

    •    “What advice would you give to future generations of our family?”

Learning about family history isn’t just about gathering facts—it’s about preserving wisdom for the future.

5. Deep Life Story Questions for Meaningful Conversations

Some of the best conversations happen when we step beyond small talk and ask deep, thought-provoking questions.

Questions That Go Beyond the Surface:

    •    “What’s one thing you’ve struggled to forgive yourself for?”

    •    “What’s a failure that turned into a blessing?”

    •    “How have your biggest mistakes shaped who you are today?”

    •    “If you could relive one year of your life, which would it be and why?”

Conversations like these build meaningful relationships and help us see the human experience in a new way.

6. Life Story Interview Questions for Career and Work Ethic

Work isn’t just about earning a paycheck—it’s a huge part of your life that shapes who you become. Our career choices, experiences with hard work, and lessons from our professional life all contribute to our personal growth.

Whether you’re interviewing a mentor, a colleague, or reflecting on your own career path, these open-ended questions can help uncover deep insights.

Powerful Questions About Work and Leadership:

    •    “What’s the biggest goal you’ve ever set for your career?”

    •    “What’s a pivotal moment that changed your professional life?”

    •    “What new skills did you develop that had the most positive impact on your career?”

    •    “How did your first job shape your leadership style?”

    •    “Who was the best team leader you ever worked with, and why?”

    •    “What’s the hardest part of being in a leadership role?”

    •    “What’s one thing about work life that younger generations should know?”

Leadership isn’t about being in charge—it’s about learning from significant challenges and developing problem-solving skills that help others. Whether you’re managing a team of professionals or just starting out, asking the right questions can help you navigate your career with clarity.

7. Using Life Story Questions to Learn From Personal Experiences

Sometimes, the most valuable lessons come from people who’ve lived through big changes—those who’ve faced negative experiences and turned them into wisdom.

Deep Questions for Personal Growth:

    •    “What’s one of the most important lessons you’ve learned from failure?”

    •    “What’s a powerful question someone once asked you that changed your perspective?”

    •    “What’s a moment in your life where you felt truly lost? How did you find your way?”

    •    “What’s the best advice your best friend ever gave you?”

    •    “What’s a part of your life you never expected to love?”

We often avoid talking about struggles, but these stories contain the most valuable insights. When we ask deeper questions, we uncover the real, unfiltered truths that shape people’s lives.

8. Family Gatherings and the Power of Storytelling

If you’ve ever been at a family reunion or holiday dinner, you know that people love sharing stories from the past. Family gatherings are the perfect time to ask specific questions that reveal important things about your roots.

Great Questions to Ask at Family Gatherings:

    •    “What was your favorite holiday growing up, and why?”

    •    “What’s a specific example of a big change in our family history?”

    •    “What’s one thing about our family that should be passed down to future generations?”

    •    “What’s the most important thing you learned from your biological parents?”

These questions don’t just entertain—they preserve memories and teach us about the unseen forces that shaped our families.

9. The Role of Books, Media, and Inspiration in Life Experiences

Stories aren’t just told through conversation. Sometimes, a favorite book or movie can shape the way a person feels about life. Asking about someone’s favorite media can give insight into their values, dreams, and beliefs.

Book & Media-Based Life Questions:

    •    “What book had the biggest positive impact on your life?”

    •    “If you could live in the world of any story, which would it be?”

    •    “What movie or show changed how you see the world?”

    •    “What book helped you through a significant challenge?”

Books, like people, have the power to change us. The stories we hold close reflect who we are.

10. The Power of Firsts: First Steps, First Things, First Lessons

Firsts matter. The first step you take toward a goal. The first thing you remember from childhood. The first big challenge you faced. These are defining moments.

First Time Questions:

    •    “What’s a first experience that changed the quality of your life?”

    •    “What was the first thing you ever felt truly passionate about?”

    •    “What’s a first mistake that taught you an important lesson?”

By asking about firsts, you uncover starting points that reveal how someone became who they are.

11. Looking at Life From a More Personal Level

Sometimes, the best way to understand someone is by asking about the small things—the daily rituals, the tiny joys, the quiet moments that bring meaning.

Simple But Insightful Life Questions:

    •    “What’s your favorite place in the world, and why?”

    •    “What’s your favorite way to spend a free day?”

    •    “What’s something small that always makes you happy?”

Life isn’t just about the biggest things—sometimes, the small town moments and new situations shape us the most.

12. How Questions Lead to a Better Life

At the end of the day, asking the best questions isn’t just about hearing great stories—it’s about learning how to live a better life.

Whether we’re reflecting on the civil rights movement, discussing long-term goals, or exploring the past, every question we ask leads us closer to understanding who we are.

Final Thought:

If you could ask just one question for the rest of your life, what would it be?

Conclusion: Start Asking, Start Telling

Life is full of questions—big ones, small ones, silly ones, serious ones. Some we answer easily. Some we wrestle with for years.

The most important thing? Keep asking. Keep telling. Keep sharing.

Because every time you ask a question, you open a door to a new story. And every story told brings us closer to understanding one another. So, what’s the first question you’ll ask today?

Feeling inspired and ready to make a change? The right guidance can turn insights into action. Whether you're seeking clarity, growth, or support on your journey, coaching can help you move forward with confidence. Schedule your consultation today and start creating the life you want.

Books That Help You Ask Important Questions & Discover Your Story

Books have a way of making us reflect on our own personal stories, guiding us through new experiences, and helping us navigate life’s big moments. Whether you’re exploring career choices, improving communication skills, or just looking for sources of inspiration, the right book can provide specific examples and important questions to shape your journey.

Here are some of the best books to spark reflection, encourage growth, and help you ask (and answer) the questions that matter most.

1. The Road Less Traveled by M. Scott Peck

📖 For: Personal Growth & Facing Life’s Toughest Questions

This classic book helps readers explore the wrong answers they’ve accepted about life and replace them with meaningful truths. It offers insights into love, discipline, and self-awareness, helping readers face the important questions about their emotional and mental well-being.

💡 Why Read It?

    •    Encourages deep reflection on personal stories and the choices that define us.

    •    Helps build resilience in dealing with health issues and emotional struggles.

    •    Offers practical steps for embracing change and new things in life.

2. Designing Your Life by Bill Burnett & Dave Evans

📖 For: Finding Clarity in Your Career Path

Feeling stuck in your career choice? This book provides specific examples of how to rethink your future using design principles. Instead of worrying about having the “perfect plan,” it helps you embrace experimentation and new experiences to build a fulfilling career and life.

💡 Why Read It?

    •    Breaks down overwhelming decisions into manageable to-do lists for life and work.

    •    Helps you identify what truly matters in your career choice and personal goals.

    •    Encourages action and learning through trial and error—there are no wrong answers in exploration.

3. The 7 Habits of Highly Effective People by Stephen R. Covey

📖 For: Leadership, Productivity & Communication Skills

Whether you’re managing a team, navigating high school, or just trying to be more productive, this book is a must-read. Covey breaks down timeless principles that improve communication skills, decision-making, and self-discipline.

💡 Why Read It?

    •    Helps develop communication skills that improve both personal and professional relationships.

    •    Offers strategies for organizing your life with structured to-do lists and goal-setting.

    •    Encourages self-reflection on important questions about leadership, values, and purpose.

4. Big Magic: Creative Living Beyond Fear by Elizabeth Gilbert

📖 For: Creativity & Finding the Courage to Try New Things

Creativity isn’t just for artists—it’s for anyone looking to try new things and embrace new experiences without fear. Gilbert shares powerful stories about overcoming self-doubt and letting go of the need for perfection.

💡 Why Read It?

    •    Inspires you to step outside your comfort zone and experiment.

    •    Encourages a growth mindset in both personal and professional life.

    •    Helps readers recognize and chase their sources of inspiration without fear of failure.

5. The Defining Decade by Meg Jay

📖 For: Understanding How Small Choices Shape Your Future

What if your twenties define the rest of your life? Meg Jay argues that the decisions we make in early adulthood—about work, relationships, and mindset—are some of the most critical ones we’ll ever face.

💡 Why Read It?

    •    Encourages self-awareness about career choices and personal growth.

    •    Explores the long-term impact of relationships, friendships, and team members on success.

    •    Provides specific examples of people who made small but powerful changes that shaped their futures.

6. The Book of Questions by Gregory Stock

📖 For: Deep Conversations & Self-Discovery

Want to dive into meaningful conversations? This book is a collection of thought-provoking questions designed to spark self-reflection and deeper questions in conversations with others.

💡 Why Read It?

    •    Perfect for asking important questions at family gatherings, social events, or personal reflection.

    •    Covers a wide range of topics, from ethics and happiness to regrets and dreams.

    •    Encourages readers to think critically and engage in deeper questions about life.

7. Grit: The Power of Passion and Perseverance by Angela Duckworth

📖 For: Building Resilience, Hard Work & Leadership

Success isn’t just about talent—it’s about hard work, persistence, and resilience. This book explores how team members, students, athletes, and professionals develop grit to push through challenges and achieve greatness.

💡 Why Read It?

    •    Great for those facing big changes and needing motivation to push forward.

    •    Offers real-world examples of people who succeeded through hard work, not luck.

    •    Encourages self-reflection on what fuels your drive and long-term goals.

8. The Power of Now by Eckhart Tolle

📖 For: Letting Go of Stress & Living in the Moment

If you’re constantly caught up in to-do lists or overthinking the past and future, this book is a game-changer. It teaches readers how to stay present, improve their mental health, and appreciate the great things in life.

💡 Why Read It?

    •    Helps you focus on what truly matters and stop stressing over wrong answers.

    •    Encourages mindfulness, making it easier to navigate high school, work, and personal life.

    •    Offers tools to manage stress, anxiety, and overthinking about the future.

9. The Courage to Be Disliked by Ichiro Kishimi & Fumitake Koga

📖 For: Self-Acceptance & Overcoming Fear of Judgment

If you’ve ever felt pressure to meet expectations, whether from society, team members, or family, this book helps you rethink how you see yourself. Inspired by Adlerian psychology, it explores how letting go of external validation leads to real freedom.

💡 Why Read It?

    •    Teaches you how to stop worrying about the wrong answers and start embracing your unique path.

    •    Encourages independent thinking and confidence in your career choice and personal decisions.

    •    Helps readers understand the importance of self-acceptance and letting go of fear.

Final Thoughts: Books Are the Best Questions

Every book in this list offers more than just words—they offer questions, challenges, and opportunities for growth. Whether you’re exploring career choices, leadership styles, personal stories, or important questions about life, the right book can give you new perspectives and push you toward something greater. So, which book will you pick up first?

Ready to take what you’ve learned and put it into action? A personalized coaching journey can amplify these insights, providing you with the support and strategies you need to navigate this chapter with clarity and confidence. Take the next step toward a stronger, more purposeful future—schedule your consultation today and start building the life you deserve.

Find Clarity and Direction with Josh Dolin’s Coaching

Life is full of important questions, but sometimes, the hardest ones are the ones we ask ourselves. If you’ve ever felt stuck, unsure about a career choice, or struggling to embrace new experiences, you’re not alone. The key to moving forward isn’t just about finding the right answers—it’s about asking the right questions first.

Josh Dolin’s coaching is designed to help you unlock clarity, build confidence, and navigate life’s transitions with intention. Whether you’re stepping into a leadership role, working on your communication skills, or simply trying to understand your personal stories, Josh helps you create a roadmap for success.

How Coaching with Josh Can Help You:

✅ Clarify Your Next Steps – Whether you’re facing a big change in your personal or professional life, Josh helps you break it down into actionable to-do lists and structured goals.

✅ Develop Stronger Communication and Leadership Skills – If you’re a team leader, working with team members, or looking to improve your communication skills, coaching provides practical strategies to build confidence and effectiveness.

✅ Find Motivation and Purpose – Sometimes, a lack of motivation comes from not asking the specific questions that reveal what truly drives you. Josh’s approach focuses on uncovering what inspires you to take action.

✅ Overcome Setbacks and Limiting Beliefs – Struggling with health issues, high school transitions, or other life challenges? Josh provides sources of inspiration and personalized strategies to help you move forward.

With Josh’s coaching, you’ll learn how to embrace new things, set long-term goals, and develop a mindset that leads to a better life.

Take the First Step Today

The most important thing about change? Taking action. If you’re ready to start asking better questions and shaping a future that aligns with your values, Josh Dolin’s coaching is here to guide you every step of the way.

📩 Schedule a free consultation today and start your journey toward clarity, confidence, and personal growth.

Frequently Asked Questions

Why is asking questions about life experiences important?

Asking deep, meaningful questions helps us reflect on personal growth, strengthen relationships, and uncover hidden insights about ourselves and others.

What are some great questions to ask someone about their life?

Some deep questions include: "What was a turning point in your life that changed everything?" or "What’s a failure that turned into a blessing?" These types of open-ended questions lead to meaningful conversations.

How can I improve my ability to ask better questions?

Focus on asking open-ended, reflective questions instead of yes/no questions. Use follow-ups like “What happened next?” or “How did that experience shape you?” to deepen the conversation.

What are some self-reflection questions for personal growth?

Some powerful self-reflection questions include: "What childhood experiences shaped me?" or "When was the last time I stepped out of my comfort zone?" Answering these helps us understand our own life journey.

How can storytelling improve personal and professional relationships?

Sharing personal experiences builds trust and emotional connection. Learning to ask engaging life questions fosters stronger relationships in both personal and professional settings.

What are some deep life story questions for meaningful conversations?

Questions like “What’s one thing you’ve struggled to forgive yourself for?” or “What’s a moment you wish you could relive?” encourage introspection and open dialogue.

Why are first experiences important in personal development?

First experiences—such as first jobs, first failures, or first passions—often shape our beliefs, work ethic, and long-term decisions.

What are the benefits of asking about family history?

Asking family members about their past preserves generational wisdom and helps us understand our roots and values on a deeper level.

How do open-ended questions encourage better conversations?

Open-ended questions encourage people to share stories, emotions, and experiences rather than giving one-word answers, making conversations more engaging and insightful.

What are good career-related life story questions?

Examples include: "What’s a pivotal moment that changed your professional life?" or "What skills did you develop that had the most impact on your career?"