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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. I’m running an “Ask Me Anything” on Friday, September 25 at 9am Pacific, 5pm UK time. I am going to discuss 5 things: (1) How to enroll high performing, high fee clients. (2) How to coach highly successful people. (3) The game that will take your coaching practice to the next level. (4) The tool that will have dream clients wanting to speak with you. (5) The power of a 20 minute chat and a 90 minute coaching conversation—and the right time and the wrong time to use each of them. Come join me!



PLUS… Whenever you’re ready… if you are a high-performing executive or entrepreneur (or you used to be) here are 3 ways we can help you increase your income and your impact—as a coach to high-performers:

Join my community of high-performing coaches and build the skills, the confidence and the powerful language you need to enroll high-performing, high-fee elite clients.

  1. Transition Excellence – 100 days of self-paced learning and group teaching/coaching with me. You will be a pioneer in our first ever cohort. 25 spots left.  
  2. Project Kairos – 9 months of live teaching and coaching from me—from January 2021 to September 2021. Deep Coaching on Zoom, month after month. A complete immersion into high-level coaching and client creation. Plus, you get a complimentary $1,500 ticket to the Rich Litvin Intensive in April 2021. The first two spots have already been reserved.
  3. The 4PC Accelerator – Accelerate your progress by 20 Years in 9 Days. I’ll be training you to step up—and out—as a thought leader. Be warned, this is a high pressure environment—where we will challenge you and stretch your thinking, so you can challenge you and stretch your clients. Plus, you’ll learn how to develop your own community of top performers and become known as the expert in your field. Only 21 spots left. 




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