Self-Coaching for Success: Key Questions to Ask Yourself

By Chris Holman
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Horsesmouth Essential: No single conversation—with yourself or someone else—is guaranteed to change the course of a business, a relationship, or a life…but any single conversation can. And it all starts with asking the right question at the right time. What is that question for you?
“The unexamined life is not worth living.”


A few weeks back, I attended Debbie Taylor’s Horsesmouth workshop, “My Journey to $1 Million.” It was a remarkable workshop. Comprehensive, forward-looking, and masterful. In fact, it was the most extraordinary workshop for financial advisors that I’ve ever attended. But, that’s a story for a different time.

In her opening statement at the workshop, Debbie stated her objective for the workshop.

“I want to change your life.”

Wow! What an assertion. Bold, fearless, and audacious…this sentence let me know that I was in for an eventful few days. And guess what? She delivered on her promise. My life was changed. But again…that’s a story for another time.

Here’s what I think. I think that all of us can change lives, one conversation at a time.

Are you with me on this? Do you think that you can change a life with one conversation? Has this ever happened to you? Have you ever changed a life, or had your life changed, with a single conversation? (I have seen it.)

Changing lives with conversation

As a coach, I believe that coaching begins and ends with the conversation. The conversation is the coaching relationship. (There’s a parallel to advisors here. Without the power of conversation, you are a…robo-advisor.)

I’ll go one step further. While no one single conversation is guaranteed to change the course of a business, a relationship, or a life…any single conversation can. This is the power that you have as an advisor, and this is my steadfast belief and reason why I love coaching. Changing lives, one conversation at a time.

And the shortcut to powerful conversations that changes lives is the question that hits you right between the eyes.

The Socratic self-coaching exercise

To illustrate the power of questions, especially coaching questions, I’ve created the following exercise. It takes about 15 minutes to complete, so you may want to do it later today, or any time you have 15 minutes when you are free to think.

Ready? Follow these six steps:

  1. Commit to spending 15 minutes with no distractions. Turn off the world around you.
  2. Scroll through the complete list of coaching questions below. Pick two questions that catch your eye, give you pause, or make you nervous.
    1. The first question should be relatively “easy” for you to answer, where you need to think about it a little bit, but not too much. This is your warm-up question that gets you thinking.
    2. The second question should be much more difficult. It might be even the type of question that causes you to inhale sharply, invokes a touch of fear, and causes you to say, “Gee…no one’s ever asked me that before.”
  3. Spend 15 minutes thinking about your responses to both questions. Don’t rush it. Take your time. This is important. Write, or type, your answers down.
  4. This exercise is just for your eyes only. Be as honest with yourself as you can possibly stand.
  5. For both of the questions that you have chosen, dig down deeper. Ask yourself the following:
    1. How is this issue having an impact on me? Or on others?
    2. If nothing changes, what is likely to happen?
    3. When the issue is resolved, what difference will it make?
    4. What is the most potent next step that I could take to move this issue toward resolution?
    5. When do I commit to taking this step?
  6. Congratulations! You’ve just begun “self-coaching” yourself. You might not have resolved anything, but you’ve put your finger on a question or issue that should give you clues for the future. Note to self: Remember this question and this topic; you’ve begun something that just might change your life.

99 self-coaching questions

  1. What is currently impossible for you to do that, if it were possible, would change everything?
  2. Where are you playing too safe?
  3. What are you avoiding?
  4. What fears fuel your resistance to change?
  5. When do you not keep your word?
  6. Where have you stopped learning?
  7. Where are you most critical? Judgmental? Pessimistic? Complaining? Negative?
  8. What are you trying to make happen in the next three months?
  9. What’s the most important decision you’re facing? What’s keeping you from making it?
  10. What responsibilities are you avoiding right now?
  11. What conversations are you avoiding right now?
  12. What do you wish you had more time to do?
  13. What things are you doing that you’d like to stop doing, or delegate to someone else?
  14. If you were hired to consult with your own company, what would you advise?
  15. What threatens your peace?
  16. What threatens your business?
  17. What threatens your health?
  18. What threatens your personal fulfillment?
  19. What do you want?
  20. What are you tolerating?
  21. Where are you not being realistic?
  22. What is it to live in alignment with your values?
  23. What is your prevalent mood? Is this a habit?
  24. Are you being “nice,” or are you being real?
  25. What do you do to avoid feelings? (Alcohol? Work? Eat? Something else?)
  26. What keeps you going?
  27. What is working?
  28. What frees you up?
  29. What is it to be prosperous?
  30. Where are you too hard on yourself?
  31. When you are at your best, what is present for you?
  32. When are you unable to laugh at yourself?
  33. What do you need to do to reach your goals?
  34. What truly motivates you?
  35. What powerful questions can you ask yourself each morning?
  36. What are you resisting?
  37. If you were at your best, what would you be doing right now?
  38. Where do you give away your power? To whom? When?
  39. What are your assumptions?
  40. What are you pretending? (To know, or not know?)
  41. What do you need to leave alone?
  42. Where do you limit yourself?
  43. Where are you too comfortable?
  44. When do you respond without thinking?
  45. Where are you selling out on yourself?
  46. Where are you uncompromising? Where are you too flexible?
  47. Where do you hold back?
  48. What are you withholding?
  49. What are you unwilling to risk?
  50. Where are you suffering?
  51. What will recharge your batteries?
  52. What do you resent or regret?
  53. What are you unwilling to change?
  54. Where are you in denial?
  55. Where are you taking your foot off the gas?
  56. What is the decision you’ve been avoiding?
  57. Where do you stop short?
  58. What have you wanted to do…but haven’t?
  59. What keeps you from winning?
  60. What have you denied yourself? Others?
  61. What complaint/bad habit/discomfort can you do something about today?
  62. What are you settling for?
  63. What are you overlooking?
  64. How do you sabotage yourself?
  65. What do you expect of yourself?
  66. What is completion? Where are you incomplete?
  67. What makes you come alive?
  68. What are your innate strengths?
  69. Where do you add the greatest value?
  70. How will you measure your life?
  71. If you weren’t afraid of failure, what would you do?
  72. What do you fear?
  73. Where are you surrendering your self-respect?
  74. What is one courageous step that you could take?
  75. What are you avoiding…due to pride, fear, embarrassment, etc.?
  76. Where are you not asking for help?
  77. Where are you overconfident?
  78. Where are you cutting corners?
  79. Where are you inconsistently reliable?
  80. When do you not “show up”?
  81. When do you not fulfill your commitments?
  82. What are your blind spots?
  83. What decision have you made, but won’t admit to?
  84. What assumptions and thinking are skewing your perceptions?
  85. What are your beliefs and biases that are shaping your story at the moment?
  86. What contradictions do you see between what you want to do…and what you’re willing to do?
  87. If you were bold enough to give up something, what would you give up?
  88. How much time do you think you have?
  89. Are there things that you really want, but have never told anyone? What are they?
  90. When do you avoid situations that might bring you into contact with people that you have problems with?
  91. When people bring up a touchy or awkward issue, do you try to change the subject?
  92. When/why do you hide behind email rather than having a face-to-face conversation that might be awkward?
  93. When do you have a difficult time saying “No!”?
  94. When do you not speak up for yourself? For others?
  95. When do you tell others what they want to know, rather than the truth?
  96. When others don’t do their job according to your mutual expectations, do you redo it yourself or hold them accountable to their promise?
  97. When are you holding back from requesting what you really want?
  98. The 4 Domains of Trust
    1. Competence: Do you have the skill, knowledge, and resources to do your job?
    2. Reliability: Do you manage your commitments…doing what you say when you say you’ll do it?
    3. Sincerity: Do you mean what you say and say what you mean?
    4. Compassion: Do you care what others care about?
  99. What is your true potential, and where/how/why are you not fulfilling it?

What questions do you ask?

As an advisor, what questions do you ask your clients and prospective clients?

Are your questions thought-provoking and different? Do they cause you to stand out as an advisor who is innately curious regarding the lives of your clients and prospects? Or are your questions just like most other advisors, e.g. ho-hum, uninspired, and boring?

If you’d like to dial up the quality of your questions, what are 1-3 questions that you’d like to start asking your clients and prospects today? (Feel free to borrow or adapt from any of the questions above.)

Thank you. I trust that you find this helpful.

Chris Holman is an executive coach with Horsesmouth. His career in financial services spans 35 years as a financial advisor, a national director of investments, and an executive coach. He is a member of the International Coach Federation (ICF), specializing in coaching financial advisors, especially through group coaching. He can be reached at


John: I think that many of our brains are wired to avoid risk and play safe. And, as advisors, your clients often expect this mindset from you. Yet, on a personal basis, we often play it too safe. It takes some doing to move from a Fear a Courage Mindset. However, to save ourselves, we must do this! Thank you for your comments!
Always knew that I was full of fear and that it was holding me back professionally. Like mold, fear that remains in the dark continues to grow, show it some light (acknowledge it and face it) and it continues to fade. Hard to do, but this is a very good exercise to begin the process of overcoming fear. Thanks Chris
Debbie: Right back atcha for your kind words. Out of all of the 99 Questions, the fear questions stand out for me. For many of us, me included, it is our fears that are most limiting. Don't you have those mornings where you wake up absolutely fearless, and ready to take on the world? And wouldn't it be great if we could have more of this? Anyway, thank you again very much!
Chris, I loved this article! Although I appreciate your kind words, I appreciate even more your passion for the business and for the people who are trying to make a difference. The 99 questions provided great prompts because we do need to ask ourselves, “What would I do next if I wasn’t so afraid?” Self coaching, or a great coach like you, can help us answer those questions. Thank you!

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