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Tom O'Leary | Ecological Coaching! Logo Tom O'Leary | Ecological Coaching! Logo
  • 💫Tom’s Journey
  • 🎙️Listen
    • 20: Your Priorities Are What You Do
    • 19: Time Defaults
    • 18: Finding Balance
    • 17: Morning Routines & Crafting Your Day
    • 16: How do I Allocate Time? (Part II)
    • 15: How do I Allocate Time? (Part I)
    • 14: How Are Environments Affecting You?
    • 13: Making The World Too Small
    • 12: Doing versus Accomplishing
    • 11: How is Past Experience Affecting You?
    • 10: Time Tenses: Past, Present and Future
    • 9: To-do Lists and Stress
    • 8: Urgent vs. Important
    • 7: Resetting Expectations
    • 6: Play and Creativity
    • 5: Not All Hours Are Created Equal
    • 4: Hard Work and Morality
    • 3: Productivity and Not Being Enough
    • 2: Thinking About Timescales
    • 1: What Represents a Good Life for You?
    • Podcast Trailer
  • 📜Read
    • What Might Regenerative Futures Look Like?
    • Challenge: What Am I Not Questioning?
    • Curiosity: A Short Manifesto
    • 🕜 Time Academy Intro to Time
    • 🕖 7-Minute Time Primer!
    • Stoic Principles
    • Musings
    • Looking for Teachers?
  • 💡Be Curious
    • 💥1-Minute Contemplation Challenge
    • 👣 Next Steps: From Reflection to Action
      • #1 How Might I Be Trying Too Hard?
      • #2 How Am I Tired?
      • #3 How Do I Resist the World?
      • #4 How Might I Deepen the Conversation?
      • #5 Where is the Silence?
    • 🎯 Decision-Making: How Do You Decide?
      • Problem Framing and Reframing
      • The Nature of Decision-Making
      • How Might I Think About Decisions?
      • Go Around the Decision-Making Table
      • Decision Coaching: What Is It?
    • ⛔ Questioning Tools & Techniques
      • A Guide to Transparent Questions
      • Socratic Method
      • The 5 Whys
      • What Might We…?
      • Step Outside the Story
      • Question Circles
      • Questionstorming
      • Mountain Exercise
      • Startup 720
      • Reverse Thinking: What Are We Not Seeing?
      • What Would Have to Be True?
    • ❢ Full List of Practice Questions
    • ❢ Time Management & Productivity
    • ❢ Reflection, Self-Awareness…
    • ❢ Communication & Relationships
    • ❢ Problem Solving & Critical Thinking
    • ❢ Creativity & Innovation
    • ❢ Values, Beliefs & Mindsets
    • ❢ Ecology, Sustainability & Regeneration
  • 🌟Think Differently
    • Curious Leaders Programme
      • 1. Foundations
      • 2. Check-in Session
      • 3. Who Am I as a Leader?
      • 4. Exploring My Limits as a Leader
      • 5. Living into More Effective Leadership
      • 6. Personal: Bringing More Awareness
      • 7. Personal: Making Space for Growth
      • 8. Where Now?
    • Coaching Playground Programme
      • 1 Personal: Bringing More Awareness
      • 2 Becoming More Conscious of the Dark
      • 3 Personal: Making Space for the Light
      • 4 Professional: Shining the Light
      • 5 Professional: Growing as a Coach: Part I
      • 5 Professional: Growing as a Coach: Part II
      • 6 Professional: Self Care
    • Bigger Questions: Where Can I Find Them?
  • 🤝How Can I Serve?
    • Let’s Begin the Conversation!
    • What Are My Options?
    • It All Starts With Your Vision
    • Leadership and Curiosity
    • The Art of Contribution
    • What Does Spending Time with Tom Feel Like?
    • Tom’s Philosophy, Principles and Values
    • Non-Executive Director & Board Advisor
  • 💫Tom’s Journey
  • 🎙️Listen
    • 20: Your Priorities Are What You Do
    • 19: Time Defaults
    • 18: Finding Balance
    • 17: Morning Routines & Crafting Your Day
    • 16: How do I Allocate Time? (Part II)
    • 15: How do I Allocate Time? (Part I)
    • 14: How Are Environments Affecting You?
    • 13: Making The World Too Small
    • 12: Doing versus Accomplishing
    • 11: How is Past Experience Affecting You?
    • 10: Time Tenses: Past, Present and Future
    • 9: To-do Lists and Stress
    • 8: Urgent vs. Important
    • 7: Resetting Expectations
    • 6: Play and Creativity
    • 5: Not All Hours Are Created Equal
    • 4: Hard Work and Morality
    • 3: Productivity and Not Being Enough
    • 2: Thinking About Timescales
    • 1: What Represents a Good Life for You?
    • Podcast Trailer
  • 📜Read
    • What Might Regenerative Futures Look Like?
    • Challenge: What Am I Not Questioning?
    • Curiosity: A Short Manifesto
    • 🕜 Time Academy Intro to Time
    • 🕖 7-Minute Time Primer!
    • Stoic Principles
    • Musings
    • Looking for Teachers?
  • 💡Be Curious
    • 💥1-Minute Contemplation Challenge
    • 👣 Next Steps: From Reflection to Action
      • #1 How Might I Be Trying Too Hard?
      • #2 How Am I Tired?
      • #3 How Do I Resist the World?
      • #4 How Might I Deepen the Conversation?
      • #5 Where is the Silence?
    • 🎯 Decision-Making: How Do You Decide?
      • Problem Framing and Reframing
      • The Nature of Decision-Making
      • How Might I Think About Decisions?
      • Go Around the Decision-Making Table
      • Decision Coaching: What Is It?
    • ⛔ Questioning Tools & Techniques
      • A Guide to Transparent Questions
      • Socratic Method
      • The 5 Whys
      • What Might We…?
      • Step Outside the Story
      • Question Circles
      • Questionstorming
      • Mountain Exercise
      • Startup 720
      • Reverse Thinking: What Are We Not Seeing?
      • What Would Have to Be True?
    • ❢ Full List of Practice Questions
    • ❢ Time Management & Productivity
    • ❢ Reflection, Self-Awareness…
    • ❢ Communication & Relationships
    • ❢ Problem Solving & Critical Thinking
    • ❢ Creativity & Innovation
    • ❢ Values, Beliefs & Mindsets
    • ❢ Ecology, Sustainability & Regeneration
  • 🌟Think Differently
    • Curious Leaders Programme
      • 1. Foundations
      • 2. Check-in Session
      • 3. Who Am I as a Leader?
      • 4. Exploring My Limits as a Leader
      • 5. Living into More Effective Leadership
      • 6. Personal: Bringing More Awareness
      • 7. Personal: Making Space for Growth
      • 8. Where Now?
    • Coaching Playground Programme
      • 1 Personal: Bringing More Awareness
      • 2 Becoming More Conscious of the Dark
      • 3 Personal: Making Space for the Light
      • 4 Professional: Shining the Light
      • 5 Professional: Growing as a Coach: Part I
      • 5 Professional: Growing as a Coach: Part II
      • 6 Professional: Self Care
    • Bigger Questions: Where Can I Find Them?
  • 🤝How Can I Serve?
    • Let’s Begin the Conversation!
    • What Are My Options?
    • It All Starts With Your Vision
    • Leadership and Curiosity
    • The Art of Contribution
    • What Does Spending Time with Tom Feel Like?
    • Tom’s Philosophy, Principles and Values
    • Non-Executive Director & Board Advisor
  • 💫Tom’s Journey
  • 🎙️Listen
    • 20: Your Priorities Are What You Do
    • 19: Time Defaults
    • 18: Finding Balance
    • 17: Morning Routines & Crafting Your Day
    • 16: How do I Allocate Time? (Part II)
    • 15: How do I Allocate Time? (Part I)
    • 14: How Are Environments Affecting You?
    • 13: Making The World Too Small
    • 12: Doing versus Accomplishing
    • 11: How is Past Experience Affecting You?
    • 10: Time Tenses: Past, Present and Future
    • 9: To-do Lists and Stress
    • 8: Urgent vs. Important
    • 7: Resetting Expectations
    • 6: Play and Creativity
    • 5: Not All Hours Are Created Equal
    • 4: Hard Work and Morality
    • 3: Productivity and Not Being Enough
    • 2: Thinking About Timescales
    • 1: What Represents a Good Life for You?
    • Podcast Trailer
  • 📜Read
    • What Might Regenerative Futures Look Like?
    • Challenge: What Am I Not Questioning?
    • Curiosity: A Short Manifesto
    • 🕜 Time Academy Intro to Time
    • 🕖 7-Minute Time Primer!
    • Stoic Principles
    • Musings
    • Looking for Teachers?
  • 💡Be Curious
    • 💥1-Minute Contemplation Challenge
    • 👣 Next Steps: From Reflection to Action
      • #1 How Might I Be Trying Too Hard?
      • #2 How Am I Tired?
      • #3 How Do I Resist the World?
      • #4 How Might I Deepen the Conversation?
      • #5 Where is the Silence?
    • 🎯 Decision-Making: How Do You Decide?
      • Problem Framing and Reframing
      • The Nature of Decision-Making
      • How Might I Think About Decisions?
      • Go Around the Decision-Making Table
      • Decision Coaching: What Is It?
    • ⛔ Questioning Tools & Techniques
      • A Guide to Transparent Questions
      • Socratic Method
      • The 5 Whys
      • What Might We…?
      • Step Outside the Story
      • Question Circles
      • Questionstorming
      • Mountain Exercise
      • Startup 720
      • Reverse Thinking: What Are We Not Seeing?
      • What Would Have to Be True?
    • ❢ Full List of Practice Questions
    • ❢ Time Management & Productivity
    • ❢ Reflection, Self-Awareness…
    • ❢ Communication & Relationships
    • ❢ Problem Solving & Critical Thinking
    • ❢ Creativity & Innovation
    • ❢ Values, Beliefs & Mindsets
    • ❢ Ecology, Sustainability & Regeneration
  • 🌟Think Differently
    • Curious Leaders Programme
      • 1. Foundations
      • 2. Check-in Session
      • 3. Who Am I as a Leader?
      • 4. Exploring My Limits as a Leader
      • 5. Living into More Effective Leadership
      • 6. Personal: Bringing More Awareness
      • 7. Personal: Making Space for Growth
      • 8. Where Now?
    • Coaching Playground Programme
      • 1 Personal: Bringing More Awareness
      • 2 Becoming More Conscious of the Dark
      • 3 Personal: Making Space for the Light
      • 4 Professional: Shining the Light
      • 5 Professional: Growing as a Coach: Part I
      • 5 Professional: Growing as a Coach: Part II
      • 6 Professional: Self Care
    • Bigger Questions: Where Can I Find Them?
  • 🤝How Can I Serve?
    • Let’s Begin the Conversation!
    • What Are My Options?
    • It All Starts With Your Vision
    • Leadership and Curiosity
    • The Art of Contribution
    • What Does Spending Time with Tom Feel Like?
    • Tom’s Philosophy, Principles and Values
    • Non-Executive Director & Board Advisor

Full List of Practice Questions

Nurturing Curiosity: Full List of Practice QuestionsTom O'Leary - Ecological Coaching2025-01-16T14:47:21+01:00

Time Management & Productivity

  • #1: When Am I Typically Most Productive?
  • #5: How Might I Make it Easier?
  • #6: At What Timescale Am I Playing?
  • #7: What Am I Doing Unconsciously?
  • #10: How Do I Know That I Am Doing Enough?
  • #23: How Do I Know What Is Important Today?
  • #26: How Are My To-Do Lists Stressing Me?
  • #28: How Do I Balance Past, Present & Future?
  • #38: How Do I Allocate My Time?
  • #40: How Is My Morning Routine Serving My Day?
  • #41: Do I Feel My Life is Balanced?
  • #42: What Are My Time Defaults?
  • #47: What Priorities Am I Living?
  • #52: Why Do I Multitask?
  • #56: What Is My Relationship With No?
  • #264: How Do I Think About Efficiency and Effectiveness?
  • #329: What Really Matters in Life?
  • #331: How Might I Delegate More Effectively?

Reflection, Self-Awareness & Personal Growth

  • #2: How Might We Listen to Our Future Selves?
  • #4:To What Do I Not Pay Attention?
  • #8: How Can I Balance the Present and Future?
  • #21: What Do I Expect?
  • #32: How Is Past Experience Affecting Me?
  • #57: Why Do I Do What I Do?
  • #78: When Do I Decide to Cut My Losses?
  • #79: Who Am I in a Group?
  • #80: Where Is the Space in My Life?
  • #84: What is Good Enough?
  • #93: What Help Am I Walking Past?
  • #97: Do I Learn More from Questions or Answers?
  • #100: How Do I Experience the World?
  • #102: How Should the World Look?
  • #106: How Am I Hiding?
  • #109: What Beautiful Questions Am I Asking?
  • #118: What Thoughts Do I Never Have?
  • #212: Where Is My Sanctuary?
  • #296: What Question Is Important for Me?
  • #311: What Have I Changed My Mind About?
  • #326: What Do I Need to Thrive Today?

Communication & Relationships

  • #14: How Do I Make Commitments to Myself?
  • #17: Why Are We Having This Meeting?
  • #20: What Was Most Memorable Today?
  • #54: What Conversations Do I Need to Nurture?
  • #115: How Do I Feel I Am Disappointing Others?
  • #116: What Expectations Do I Create for Conversations?
  • #151: What Conversations Am I Avoiding?
  • #176: How Do I Measure Diversity of Thought?
  • #200: What Concerns Might Stakeholders Have?
  • #208: What Makes Conversations Valuable?
  • #209: Who Isn’t in the Room?
  • #217: How Am I Contributing to the Conversation?
  • #229: How Do I Tend to Relationships Over Time?
  • #256: How Do I Greet Others?
  • #278: What Is Taboo?
  • #285: What Responsibility Do I Have for Being Heard?

Problem Solving & Critical Thinking

  • #125: What Choice Architectures Do I Create?
  • #126: What is the Goal of My Pricing Structure?
  • #131: Why Am I Asking This Question?
  • #133: Where Am I Not Looking for Ideas?
  • #173: How Might Poetry Help Me See Clearer?
  • #188: How Am I Curious?
  • #189: What Is Possible Now?
  • #191: Can I See Fresh Questions?
  • #192: Where Might I Go to Meet Inspiration?
  • #193: What Can I Learn From My Weaknesses?
  • #205: What Do I Know?
  • #210: How Can I increase the Psychological Value of Everything I Do?
  • #226: What Role Does Social Proof Play in My Decisions?
  • #235: How Does This Qualify as a Problem?
  • #258: What If We Solved the Meta Problem?
  • #287 What Is the Biggest Challenge My Clients Have?
  • #320: What’s Obvious Now?

Creativity & Innovation

  • #19: How Do I Interrupt Myself?
  • #30: Can I Accomplish Something Without Doing Anything?
  • #108: What Rules Do I Set for Myself?
  • #112: What Might I Unlearn Today?
  • #117: What Am I Certain Of?
  • #123: What is My Relationship With Boredom?
  • #124: What If I Treated Everything as a Trial?
  • #127: Where Is the Upside Optionality in My Day?
  • #140: What Energises Me?
  • #143: What Game Am I Playing?
  • #149: How Might I Disrupt My Own Thinking?
  • #150: Am I Playing to Win or Not to Lose?
  • #159: How Much Space is in My Diary?
  • #219: What Opportunities Might Be Waiting for Me?
  • #222: What Choices Do I Not Know I Have?
  • #246: How Open Am I to Curiosity?
  • #366: What Are Questions? And Answers?

Values, Beliefs & Mindsets

  • #9: What Fears Drive Me?
  • #130: What Can I Do Today to Shape My Legacy?
  • #136: What Have I Settled For?
  • #141: What Story Have I Told Too Many Times?
  • #175: What Is Beyond My Control?
  • #177: How Badly Have I Failed?
  • #179: What Are My Values?
  • #199: What Can My Stress Teach Me?
  • #201: Who Is the Master & Who Is the Student?
  • #202: How Am I Being Defensive?
  • #206: How Am I Being Impatient?
  • #213: What Really Interests Me?
  • #237: How Am I Deluding Myself?
  • #255 Why Don’t Good Things Last in My Life?
  • #257: Who Do I Feel I Need to Be?
  • #294: What Is My Relationship with Feedback?
  • #325: What Does High Performance Mean to Me?
  • #328: Am I Being My Best Self?

Ecology, Sustainability & Regeneration

  • #337: How Might Sustainability Be More Sustainable?
  • #357: What Do I Have to Say?
  • #362: Where Does the Environment Begin?
  • #363: What Choice Do We Have?
  • #364: How Can We Be Good Stewards?
  • #367: What End Do Goals Serve?

Connect on LinkedIn

Tom O'Leary

Practice Questions by Category:

  • Full List of Practice Questions
  • Time Management & Productivity
  • Reflection, Self-Awareness & Personal Growth
  • Communication & Relationships
  • Problem Solving & Critical Thinking
  • Creativity & Innovation
  • Values, Beliefs & Mindsets
  • Ecology, Sustainability & Regeneration

Questioning Tools & Techniques:

  • Overview
  • A Guide to Transparent Questions
  • Socratic Method
  • The 5 Whys
  • What Might We…?
  • Step Outside the Story
  • Question Circles
  • Questionstorming
  • Mountain Exercise
  • Startup 720
  • Reverse Thinking: What Are We Not Seeing?
  • What Would Have to Be True?

Looking for Inspiration?

  • Challenge: What Am I Not Questioning?
  • Curiosity: A Short Manifesto
  • Leadership and Curiosity
  • Corporate Sustainability: What are Boards Trying to Sustain?
  • Nurturing Curiosity in Kids
  • Nurturing Curiosity: Daily Practice
    • Decision-Making: How Do You Decide?
    • Questioning Tools & Questioning Techniques
    • Practice Questions by Category

Learn to Question What Others Can’t Even See!

Receive a thought-provoking question weekly to stimulate how you think & what you question.

BONUS: Time Academy Guide

What Might be Possible If We Believed It Were Possible?

Questions have a strange power. They can release us from what we believe to be true by offering us glimpses of something different. Indeed, there are times in that brief moment after a question is asked when it feels like anything is possible.

How then can be capture more such moments and infuse them into our decision-making? The science of decision-making is in truth an art we spend our lives practicing. The same goes for curiosity and innovative thinking.

We make decisions all day every day. Some echo for minutes, others for months whilst a few echo throughout our lives. How do we distinguish and decide accordingly?

That is why I am a big advocate of nurturing curiosity and innovative thinking at all ages. If you are a leader, you will no doubt already know that continually nurturing curiosity in leadership is absolutely key. In many ways, leadership begins with self-leadership, which is in turn built on a deep sense of curiosity about who you are as a person and as a leader and at its core about how you make decisions. In fact, how did you decide to read this? And, what will you decide to do next?

What Might be Possible If We Believed It Were Possible?

Questions have a strange power. They can release us from what we believe to be true by offering us glimpses of something different. Indeed, there are times in that brief moment after a question is asked when it feels like anything is possible.

How then can be capture more such moments and infuse them into the building blocks of our lives, namely the countless decisions we make every day? The science of decision-making is in truth an art we spend our lives practicing. The same goes for the other critical soft skills we need to nurture if we are to truly think differently, particularly if we are in leadership.

In a world rushing towards the next thing, my invitation is to focus on contemplation over mere action. Humans are very good at solving problems but less so at ascertaining the right problem to solve. By slowing down enough to nurture curiosity and find deeper insights, we ensure that we are at least answering the right question, saving energy and resources and obtaining better outcomes.

Afterall, if we are answering the wrong question, it doesn’t matter how ‘hard’ we work, we are still answering the wrong question.

In fact, what question matters most to you right now?

One of my key questions right now is “How might we build more bridges to regenerative futures?” In an effort to live into this question, I contribute to the weaving of regenerators in Ireland via the Regenerative Futures group. I have also co-founded regening, a Kerry-rooted eco-social enterprise working to catalyse an equitable society that cares for people and planet – now and for the future.

This complements my one-to-one work with bold pioneers – what I call Ecological Coaching – on the inner transition that will power their organisation’s outer transition towards more regenerative futures. This approach views leaders not just as individuals but as integral parts of a network of relationships. Within this ecosystem, I help leaders feel heard, gain clarity, take decisive action, build confidence and thrive — all in service of something bigger.

This could thus equally be called Regenerative Coaching because the intent is to create a positive feedback loop between the leader, the organisation, those it serves and the planet that nourishes us. In this respect, the four core questions when making a decision are, to build on Daniel Christian Wahl – author of Designing Regenerative Cultures:

  • Does this serve me?
  • Does it serve my organisation?
  • Does it serve our communities (customers, suppliers, local communities)?
  • Does it serve life?

The journey is ultimately about putting the fourth question first and seeing ourselves as being in service to life.

Tom O'Leary ¦ I Believe Curiosity Spurs Performance ¦ What About You?
Tom’s innate ability to listen and empathise enabled me to relax and really explore the issues that were causing me some anxiety. Our sessions provided me with an enhanced sense of self-awareness and a considered plan of action. The benefits in terms of relationships and self-confidence this process has given me are invaluable, in both work and life in general!
Testimonial from Sean
I went for coaching with Tom, without knowing what I wanted but knowing that I needed some help after having a number of setbacks with interviews. By the end of the first session, I was beginning to realise my problems. By the end of the second session, I was beginning to realise what I wanted. In our final two sessions, Tom helped me to identify a strategy for achieving my goals.

I thoroughly enjoyed our sessions. Tom listened without judgement, guided without being opinionated and ultimately helped me to help myself. You can’t ask more from a coach.

Testimonial from Paul

I didn’t think I had a specific need for a coach, however, having met Tom outside of our professional roles we decided to set up a coaching programme. I’m delighted we did. Tom’s approach is based on taking it slow, listening first and asking questions you won’t have thought of second. The latter always result in positive actions to take away and implement immediately. Now, I’m really looking forward to continuing our working relationship.

Testimonial from James Crothall, Account Director at AMO DIGITAL

I’ve been catching up with Tom for now, over three years. It is a moment where I’m able to create space away from the noise and the busyness of my life to really tackle whatever is top of my mind. This can be on the professional side and can be on my personal side. My conversations with Tom are really conversations we have dialogues that we have, and a walk away from these meetings with clarity around ideas of how to convey pragmatically and practically tackle some of the challenges and the issues which I wanted to discuss with Tom. But I think more importantly, with a greater degree of confidence in my ability to solve for these topics. I’ve been really enjoying my catch up with Tom I hope to continue to do so in the future and I highly recommend anybody to give it a go.

Testimonial from Tommaso
Tom’s innate ability to listen and empathise enabled me to relax and really explore the issues that were causing me some anxiety. Our sessions provided me with an enhanced sense of self-awareness and a considered plan of action. The benefits in terms of relationships and self-confidence this process has given me are invaluable, in both work and life in general!
Testimonial from Sean, Ireland
I went for coaching with Tom, without knowing what I wanted but knowing that I needed some help after having a number of setbacks with interviews. By the end of the first session, I was beginning to realise my problems. By the end of the second session, I was beginning to realise what I wanted. In our final two sessions, Tom helped me to identify a strategy for achieving my goals.

I thoroughly enjoyed our sessions. Tom listened without judgement, guided without being opinionated and ultimately helped me to help myself. You can’t ask more from a coach.

Testimonial from Paul, Ireland

I didn’t think I had a specific need for a coach, however, having met Tom outside of our professional roles we decided to set up a coaching programme. I’m delighted we did. Tom’s approach is based on taking it slow, listening first and asking questions you won’t have thought of second. The latter always result in positive actions to take away and implement immediately. Now, I’m really looking forward to continuing our working relationship.

Testimonial from James Crothall, Account Director at AMO DIGITAL
Tom O'Leary - Your Thinking Partner

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