Ten of Bobb Biehl’s All-Time Favorite Questions

Guest Post by Bobb Biehl

Note from Bob:  Bobb  Biehl, is for me, the wisest man I have ever met!  I have been privileged to call him my friend and my personal mentor since 1980.   It was then – in 1980 – that Bobb first introduced me to his hobby of collecting questions. 

What is the very best question you’ve ever been asked?

What are the favorite questions you ask others?

Doesn’t it feel great to ask, or be asked, just the right question at just the right time?

If you ask shallow questions you get shallow answers.

If you ask profound question you get profound answers.

If you get if you ask no questions you get no answers at all!

Here are 10 of my all-time favorite questions:

ONE:  One of life’s most powerful questions: Why? … Why? … Why? … Why?

When you ask this question, you get to the bottom of any issue very quickly.  It addresses purpose, reason, foundation. Once you ask the question “why” go back and ask “Well why is that important”.  You get ever deeper into any subject.

TWO:  An ideal question: What is the ideal-long term? 

This question moves you past shallow solutions.  It moves past temporary solutions.  It moves you toward ideal solutions for the deep future.

THREE:  A question to help you gain a quick big picture: “If we could only do 3 measurable things in the next 90 days which would make a 50% difference, what would we do?” (Steve Douglass)

Steve Douglas taught me this question years ago.  I’ve used it hundreds of times since. If we could do only three things (focuses your priorities), in the next 90 days (addresses time), to make a 50% difference (clarifies results) what would we do?  This one question immediately addresses priority, time, and result. Great question Steve!

FOUR:  To quickly focus your next year, ask: If I could only accomplish 1 measurable thing in the next year … what would I do?

This is a very profound question, as it clarifies your activity for an entire year.  It moves to a 50,000-foot view of what you would like to do.  In seconds, it gets you beyond day-to-day detail into the largest picture possible for the coming year!

FIVE:  To understand your (or another’s) adult comfort zones ask: What was your life like in the 4th grade?

The 4th grade? (Age 9) is the single most shaping year in a human being’s existence. Age 9 is where our comfort zones are established.  What you were comfortable doing the fourth grade is what you’re comfortable doing today as an adult.  When you get to understand a person‘s fourth grade you get to know a person’s adult comfort zones.

SIX:  To help get to know a person’s life long dreams ask: How do you plan to make the most significant difference in your lifetime?

With this question, you get to know how a person plans to make a difference that will last for eternity.  This question gives you a very fundamental and deep insight into who the person really is – and, what their life long values are today.

SEVEN:  When you know a person really well ask: What 3 changes in your life would be most pleasing to God?

This question gives you a very deep insight into a person spiritual development.  It gives you a look at where the person really wants to grow personally, and needs to grow spiritually.

EIGHT:  To maximize a person ask: Of all the things you do well – What do you see as your single greatest strength? What do you do the very best?

When you get a look at the person single greatest strength you know the most effective way to work with them – to help her / him to reach full life potential.

NINE:  A great non-threatening counseling question to ask friends: Is there something heavy on your shoulders today?

This question can be answered quickly with a very specific need the person has.  Or, your friend can simply answer, “Nothing today – thank you” which in essence says, “No but thanks for asking”.  Or, “Stop asking!”.  It is a nonthreatening question that has led to many deep and very personal discussions.

TEN:  A great career counseling question: If you could do anything you wanted, had all the time, money, staff, education you needed, and knew for certain that you couldn’t fail, what would you do?

This question opens up many discussions in terms of persons ideal direction in life.  It also gets the person beyond a frequent answer, “I would do this if I couldn’t fail”.  It has helped hundreds of people clarify their future direction very quickly!

Friend, what are your 10 favorite questions – why are they your favorites?

These questions were taken from a pocket booklet (in its 30th printing) titled Asking Profound Questions available at BobbBiehl.com



Bobb Biehl


Bobb Biehl is an Executive Mentor.   In 1976, he founded Masterplanning Group International. As its president, he has consulted personally with over 500 clients. In that time, he has met one-to-one with over 5,000 executives

Based on these thousands of hours of practical “rubber-meets-the-runway” experience, he has originated 35 leadership / management tools (books, tapes, notebooks) in the area of personal and organizational development – all of which are available to you at BobbBiehl.com 



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2 thoughts on “Ten of Bobb Biehl’s All-Time Favorite Questions

  1. Janet Wunder says:

    This little booklet has been a go-to resource for me over and over again. The author’s questions helped me clarifying some of life’s challenges and have become a companians on my journey.

    1. Bob Tiede says:

      Janet – I absolutely agree! Bobb Biehl was the very first person who ever shared with me the value of questions!

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