How to Ask Yourself Great Questions

In my life coaching training program, one of my first homework assignments was to make a list of 100 empowering questions we could ask clients in coaching sessions.  These are open-ended questions that generally begin with the word how, why or what.  They elicit more than a yes, no or simple answer.

These deep and powerful questions can help us connect with who we really are: our true selves.  They can also help clarify our values and stimulate creativity.

I figured I would blaze through this assignment initially, putting down as many questions as I could.  In fact, that was all we were required to do.  Fortunately, I took this assignment a step further…

Going deep
I thought to myself: what if I really focused on something that I wanted to shift or change in my own life?  This birthed my first question: what is it that I want?  Instead of jumping right to another question, I contemplated this one for a while.

In thinking about my private practice, my answer was “to have an attractive website where potential clients can learn things about themselves and reality, and where they can get a good sense of how I can help them.”  Despite the satisfaction my answer brought, it naturally brought to mind another question: how can I get that?

My response was: “through carefully planning out my site, including writing good and engaging copy, having nice graphics, a good layout, and a site that offers them [clients] something they haven’t gotten elsewhere.”  Again, I noticed another question welling up inside in response: what stands in my way?

“Overwhelm.  I feel overwhelmed by all there is to do.  I don’t know where to start.  Or if I do, I find myself having to take a step back and do more before I can lay down a foundation. There’s an attitude of perfectionism which may be connected to my wanting to do it right…”

Interestingly, things were getting stirred up.  Each answer brought to mind another empowering question.  I would sit and ponder each until it was fully answered.  An inner dialog had inadvertently developed.

Destination unknown
In the end, I went somewhere I didn’t expect to go and gained clarity in the process.  The assignment obviously took much longer than anticipated.  But, I was much more immersed in it than if I had simply rattled off a list of questions.

My takeaway was that I could turn to this process of asking empowering questions whenever I wanted to shift, change or examine something in my life.  I could also offer it as an exercise to future clients.

Your turn
I invite you to follow the process I used.  First, think about something you’d like to shift, change or more closely examine in your life.

If you’re stuck, then simply start with this question: “what do I want to shift, change or really look at in my life?”  Consider either the problem or issue at hand, or the end goal or ideal outcome.

After giving this serious thought, actually write down (or type) an answer to this question.  This will help make your inquiry more tangible, getting it out of your head.  It also allows you to go back and review previous questions more easily.

Next question please
Next, let the answer guide you to the next logical question.  If the next question doesn’t come easily, consider what someone else might ask you based on your answer.

If you notice that the questions get deeper and more difficult to answer as you proceed, then this is a good sign.

However, if an answer doesn’t come at all, really sit with or sleep on the question.  Return to the inquiry at another time.  Ironically, this might help you answer the question, even if you’ve forgotten all about it.

Each answer can be as long or as short as it needs to be.  The key is giving every question sufficient time to marinate in your mind.

All done?
So, how do you know when you’re done?  Well, it has little to do with how many questions you’ve answered.  Overall, you should feel satisfied with the process, even if you don’t like or agree with all of your answers.

This might mean that something gets stirred up, you see the problem or issue in a new light, you internalize what you know intellectually, you gain insight, etc.  Whether you’ve gotten your final answer or you’ve reached a new plateau, it is the journey that is most important.

Now, go forth and ask yourself great questions.  I’d love to hear how it goes in the comments…

Jack Grabon, LCSW, CPC practices spiritual therapy and holistic life coaching, helping those on a spiritual path to resolve issues and live happier, more meaningful lives.  He offers in-person sessions in New York City, as well as phone and Skype sessions.  Contact him now for a free consultation.

15 Responses to How to Ask Yourself Great Questions

  1. sarvajeet says:

    hey jack. nice article. Great Technique to arrive at what you want. It starts with big question and when you see the final answer it will be a really small step or initiative which will ultimately result in big success. Rightly said, journey or process is important. Thanks for this technique which is simple, easy and really effective.

  2. Hi, jack. It’s such a good post of yours. Many times in my life, when I’m stuck, i ask a lot of questions to myself. Even when my life is going great, i stand back and pause for awhile and then evaluate myself. I count up my blessings and try to remain happy for every moment.

    Really good article. I appreciate it.

  3. julip says:

    thanks for this. stumbled upon it and now questioning seems the answer.

    i like when that happens.

    i’ll go pick the brain and see what grows.

  4. Ericson Ay Mires says:

    I like how the method is really philosophical in nature. These deep, stream of consciousness forms of questions undoubtedly would lead to deeper insight into who you are and what you want.

    There’s also an important emphasis on process going on here, focusing on letting the answer come to you rather than forcing it out.

    I found the article to be quite good, great job.

  5. Jack Grabon says:

    Thanks Ericson, glad you enjoyed the article. The key is to let the answer come and not to force it. This is all about process.

  6. Jack Grabon says:

    That’s funny julip, but you’re right. Questioning may be the answer, as they certainly can help us get answers and ask better questions.

  7. Jack Grabon says:

    Thanks for the feedback Sandeep :-) Glad you resonated with the post.

  8. Jack Grabon says:

    Thanks sarvajeet. I’ve found that things tend to be simple, although not necessarily easy as they may take much effort. Glad you enjoyed the post :-)

  9. This was so helpful. I want more control over my work so I can focus on doing it in a way that I enjoy and in a way that would be most helpful to my clients. Figuring out each action step moving in that direction is so hard, not knowing what to do next. Then trying something new and fearing people will think your ideas are stupid. Getting positive feedback, and believing you don’t deserve it.
    Glad I got that out of me! Feel better already. Great article 😉

  10. Patti Murphy - PM Mediation says:

    Hi Jack! Wonderful post! This is a great exercise to do when someone or something invokes a strong response or feeling; like hurt, anger or disappointment. You can ask yourself questions such as “why am I experiencing this feeling” or “what did these words or actions trigger in me”? Then, “understanding why I was triggered, what future actions or responses would better serve me and others”.

    Thanks for reminding us to think deeper, see what emerges and to enjoy the journey!

  11. Jack Grabon says:

    Thanks Carmen, glad you got a lot from the article! The great thing about this process is that it not only helps with actions and working towards goals, but with thoughts, feelings and beliefs that precede them as well.

  12. Jack Grabon says:

    Really glad that you enjoyed the post, Patti. The nice thing about this process is that it can be used for almost anything. I think of it as a form of self-coaching that anyone can use.

  13. Shawna says:

    This came at a good time because i feel the plateau within my career once more. But, then using this technique, as well as a walk through the woods with my dog to let that stream of consciousness flow, I found one answer! I am excited to continue to use the questions as I journey down a new idea within my field!

  14. Jack Grabon says:

    Thanks for sharing Shawna :-) Always nice to hear the process working well.

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