Questions For Digging Deeper

Digging Deeper With Questions

With a little bit of practice buoyed by our innate sense of being curious, we all have the ability to become explorers without ever leaving home.

Digging deeper into the details and bigger picture creates distinctions that open the way to greater awareness and clarity. Words move beyond generalities to have the richer meaning. Assumptions turn into deeper understandings. Situations and dilemmas begin to unfold.


I used this exact process of questioning to dis cover what was driving my desire to purchase a new kitchen table.






These inquiries will start you digging. Be sure to read the next post for tips on approaching questions before you get started. When you are exploring a situation or decision for clarity, replace “___word__” in the sentence accordingly.


What is your experience of [ __word__ ]?

When you talk about  [ __word__ ] what you really mean is ___________________.

[ __Word__ ] also leads you to think of ___________________.

Other words or phrases you might use instead of [ __word__ ] would be ___________________.

When you think of [ __word__ ] you feel ___________________. And that leads you to feel ___________________.

Do you think of [ __word__ ] differently in different circumstances?

How might other people think of  [ __word__ ]?

Where else do you encounter [ __word__ ] in your life?

[ __Word__ ] always seems to come up when you are ___________________.


More questions from the kitchen table to poke around:

What’s really going on here?

How will life be different when I have [ __item__ ]? What will I have that I don’t have now?

What will I be able to do when I have [ __item__ ]?

And most importantly – who am I being before and after I have [ __item__ ]? When else am I being that way?


You might find this drill down technique useful to gain even more clarity. This technique is especially powerful when you are looking for clarity around a decision, situation or change you want to create.

What does [ __word__ ]  mean to you?

And that is important because?

And that is important because?

And that is important because?


Why this works:

We tend to stop at the first answer that comes to us. Each time you inquire about the importance about the previous answer you access a new level of understanding. The hidden nuances begin to reveal themselves. Three levels down is usually enough, but keep drilling down until you hit the gold nugget. You’ll know when you do. The body’s response to hitting something core is very clear.


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Lorraine Watson - on rustic porch

chief nudging officer


Crazy for cats and potatoes, Lorraine's insatiable curiosity of Life leads her to question, explore and push beyond the box. A self-professed "left-brained creative big picture" type, she has an intuitive knack for seeing beyond and beneath first appearances while at the same time nerding out on the details. Most of all she sees and holds others in their highest until they can see it for themselves.

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