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.


Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

2 Responses to How to Ask Yourself Great Questions

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  2. jy doll says:

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