Asking Questions

December 9th, 2013 | Leadership

Guest Post by Bobb Biehl

Excerpted with Bobb’s permission from Chapter One of his book “Leading with Confidence”

(Special Note from Bob Tiede:  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 asking questions. Bobb began collecting questions, just as some people collect stamps or antiques.  I hope you too will join Bobb and me in making both collecting and asking questions a life long hobby because as Bobb says, “Questions are essential to gaining knowledge and understanding.”)

If you and I could sit down together on a park bench on a sunny spring day and talk for an hour about any situation or problem or risk—anything you’re trying to think through and analyze and gain perspective on—what single situation would you want to discuss?

With that situation focused clearly in your mind, let’s work through the questions I would ask to help you.

What? When? Who? How? Where? How much?

Rudyard Kipling called them his “six trusted men”—the questions who, what, when, where, why, and how.  As a reporter and writer, Kipling was speaking from a journalistic perspective rather than a leadership perspective, but his questions are helpful for us as well—though we might want to ask them in a different order.

Start with What? Can you state, in just a sentence, what is the situation you want to think through today?

Why would you like to think it through? Why is it important to you? Why has this situation developed?

When did it start developing? When do you need to solve it? When do you need to deal with it? When do you need to make some changes?

Who are the primary people involved? Who caused the situation? Who is involved with it? Who is the beneficiary of it? Who benefits most? Who takes the brunt of it? Who is most affected by it?

How do we change it? How do we make a difference? How do we bring appropriate resources to bear?

And Where? Is space or place even important? Is it important to do it here in town, or maybe in a different state, or at your house or my house? Where should we do it? Whatever we do to correct the situation, how does “where” fit in?

Another important question I always add is How much? How much will it take to correct the situation? How much money? How much time? How much energy? What amount of resources will it take?

As you can see, it’s impossible to think through any situation effectively without questions. It isn’t just hard; it’s actually impossible. You must ask questions like What? Why? When? Who? How? Where? and How much?

That’s why the better you become at asking questions, the better you are at thinking through anything, anywhere, at any time, for the rest of your life.

Compared to what?

A second line of questioning I would have you consider is “Compared to what?” Nothing is meaningful without a context. So what is the context of the situation you are dealing with? What are the comparisons? What other situations are like it? What have you experienced like it before? What are the facts? And how do you compare those facts with facts in other parts of your life?

A person may be happy making five dollars an hour until he learns that someone next to him is making six dollars for doing the same thing. Now he has a different context for evaluating his situation.

A senior executive once said to me, “Bobb, we’re $50,000 in the red this month.” I think he expected me to turn pale, but instead I calmly asked, “Compared to what?”

He answered, “What do you mean, ‘Compared to what?’ We’re $50,000 in the red this month!”

“Well,” I said again, “compared to what? If you were projected to be $100,000 in the red, then you’re actually in great shape now! If you expected to be $50,000 in the red, you’re right on target. And if you were supposed to be $100,000 in the black, you’re in deep trouble.  So…compared to what?”

At that he answered, “Well, our projection was that we’re sup-posed to be $46,000 in the red.”

“Then relax,” I said. “What else do you have to talk about today?”

Maybe you too can relax as you gain the perspective of context. What’s the context of the situation you’re dealing with today—the broader pictures?

For example, what difference will this situation make ten years from now? In other words, what is the context of time and how will time affect it?

What is the context of money? How much would the problem cost to correct, and how does that amount compare with all the money you made this year, or all the money you’ll make in your lifetime?

What’s missing?

The third line of questioning focuses on these two words: What’s missing? Frankly, I believe our education system today fails to teach us this profound question, but leads us instead to be analytical only about what we see.

What missing information is making it difficult for you to get a clear understanding of your situation? What facts do you need to gather to help you see it more clearly?

This is one of the hardest questions to remember to ask yourself, but it frequently unlocks solutions for problems that otherwise just can’t be solved.

When any situation has you confused, simply asking “What’s missing?” often leads to a major breakthrough.

What is the ideal in this situation?

Another question you’ll want to use over and over again is “What is the ideal?” It’s actually an “ideal” question—it fits nearly everything.

In the situation you’re dealing with—what would be the ideal solution? What would be the outcome if everyone involved acted in an ideal manner? If you had the ideal amount of money? The ideal amount of equipment? The ideal facility? The ideal everything? Ideally, what would we have that we don’t have now? And how much of that is truly critical?

Develop an insatiable commitment to seeking the ideal. Build this into your thinking so that until you reach the ideal, you will always have a slight dissatisfaction in your mind.

Until you recognize what the ideal is, you don’t know precisely the distance between where you are and where you’d like to be or could be.

What would my five closest friends advise me?

If you asked your five closest friends to help you deal with this situation, what advice would they offer? Often, just imagining their response gives you needed perspective.


 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 


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