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35 questions that will change your life

You have a superpower, as a coach, that most people will never have. It’s your ability to ask great questions. But asking great questions is a skill that needs to be nurtured. 

I have been collecting and curating great questions for over 20 years. Several years ago, I published a list of 121 of the most powerful questions I know. But I didn’t stop there. I have continued to collect questions. I have continued to challenge my clients to answer the hard questions that no one else is answering. And I continue to ask myself those same hard questions. 

Today I want to ask you some of the most powerful questions I have asked or been asked in the past decade. 35 questions, grouped into 4 categories—the past, the present, the future and no regrets.

Great lawyers never ask a question they don’t know the answer to. Great coaches never ask a question they do know the answer to. 

Ask the following questions of your clients and you will rock their world. Answer these questions yourself and you will change your life. 

The Past

  1. What are your top 3 business or career successes—that you are most proud of? (The impact you’ve had, the difference you’ve made, the income you’ve created, the acknowledgements you’ve received. You’d be surprised how hard it is for people to share what they are proud of).
  2. What are your top 3 personal or life successes—that you are most proud of? (Family, relationships, growth, health, contribution).
  3. What are you known for? What can people count on you for?
  4. What is the hardest thing in business/life that you have overcome? What did you learn from the experience?
  5. What has your revenue been, each year, for the past 3 years? Why wasn’t it higher? Why wasn’t it lower? 
  6. What has your profit been, each year, for the past 3 years? Why wasn’t it higher? Why wasn’t it lower? 
  7. How much time off have you taken, each year, for the past 3 years? Why wasn’t it higher? Why wasn’t it lower? 

The Present

  1. Make a list of all the goals you have, right now. Which ONE, if you focused on it—to the exclusion of every other goal—would be most likely that you’d achieve over all the others, anyway?
  2. What will you do to ensure you make this happen—no matter what?
  3. What are you willing to sacrifice to achieve your goals? What are you not willing to sacrifice? 
  4. What are the three biggest reasons your life, business or impact isn’t yet where you want it to be?
  5. What’s missing from your life and/or business? And how do you keep it out?
  6. What do most people do in business that you do differently? Does that help you thrive—or struggle?
  7. What is the problem you really solve for your clients?  
  8. What is the single most important result your clients get?

The Future

  1. What would you like to accomplish—that may look impossible, right now—but if it were achieved would change everything?
  2. If you were to look back 3 years from now, and say, They have been the best 3 years of my life—what has to have happened, for you to feel thrilled with your progress?
  3. What were the 3 tiniest shifts that made the biggest difference in those 3 years?
  4. If you were to look back 3 years from now, and say they have been the worst 3 years of my life, why will that be? eg. unhealthy relationships, poor habits, limiting beliefs, fear of success.  
  5. What habits held you back the most in those 3 years?
  6. How will you NOT achieve what you want, in the next 3 years? (We always know, in advance, how we tend to fail at things. Let’s identify that now, so we can handle it).
  7. What’s one truth – that you’ve held back – that you know the world needs to hear?

No Regrets

Bronnie Ware worked in palliative care for many years and she wrote a book called The Top Five Regrets of the Dying. The following questions are designed to help you live a regret-free life:  

  1. How are you living a life that others expect of you, rather than a life true to yourself?
  2. What (secret) dreams do you have that are still unfulfilled?
  3. What (secret) choices are you making – or not making – that is having these dreams remain unfulfilled. 
  4. What (secret) choices are you making – or not making – that negatively impact your health in the present? Or more importantly, in the future?
  5. Why are you working so hard to spend so much of your life on the treadmill of work? What are you sacrificing to do so? Is it worth it? Will it be worth it in ten years?
  6. Where do you not have the courage to express your feelings? What’s that costing you? What would it be worth to you to change that?
  7. Reflect on a moment when you wanted to speak truth to power – or express yourself – and you did not. Why didn’t you? And what was the result of that? 
  8. Reflect on a moment when you did speak truth to power – or express yourself. What was the result of that? (Inside you and out in the world).
  9. Which friends have you lost touch with? Which friends do you miss? What tiny action could you take to reconnect with an old friend?
  10. Where are you stuck in old patterns and habits that don’t let you be happier? 
  11. If you could laugh properly and have silliness in your life again, what would you do?
  12. What’s your greatest regret so far? 
  13. What will you set out to achieve or change before you die?

Don’t let this be just another interesting article. Pick one question and answer it. Start with the easiest question—or start with the question that makes you clench up the most. Your choice. Block out an hour to answer as many questions as you can, or answer one question a day for a week. Refuse to answer the questions but ask them of all your clients. Answer them alone. Or gather a few close friends to answer them together. Send me your answers or keep them to yourself. Your choice. 

You do not rise to the level of your answers. You fall to the level of your questions.

Love. Rich 


PS. Dramatically increase your confidence as a coach by mastering enrolling clients. Drastically increase your ability to raise your fees and up-level your clients. And learn to have fun making money. Join me on The 90 Day Money Game. There’s still time to join us…   


PLUS, whenever you’re ready – here are 4 more ways you can drastically increase your income and impact as a world-class coach:

  1. Assess your current coaching level and learn how to get to your next level. Read – or remind yourself of – The Litvin Levels, from The Prosperous Coach.
  2. Watch me coach some of the top coaches on the planet, in order to drastically uplevel your coaching skills. Join me on How To Coach A Superhero: The 4PC edition
  3. Imagine joining a Deep Coaching experience alongside the members of 4PC, my community of high-level coaches… We only offer The 4PC Accelerator once a year and it always sells out in advance. Save $1,000 with early-bird pricing.
  4. Learn how to enroll and coach successful, talented and ambitious clients – with power and impact. Join my flagship program, Project Kairos – for 8 months of guidance, challenge and support to master creating clients.


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