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The Thinker’s Toolkit

14 Powerful Techniques for Problem Solving

by Morgan D. Jones — Former CIA analyst







Part One — Why We Go Astray

1 Thinking About Thinking

2 Insights into Problem Solving

Part Two — The Fourteen Tools

3 Problem Restatement

4 Pros-Cons-and-Fixes

5 Divergent/Convergent Thinking

6 Sorting, Chronologies, and Time Lines

7 Causal Flow Diagramming

8 The Matrix

9 The Decision/Event Tree

10 Weighted Ranking

11 Hypothesis Testing

12 Devil’s Advocacy

13 The Probability Tree

14 The Utility Tree

15 The Utility Matrix

16 Advanced Utility Analysis

Part Three — Where Do We Go from Here?

17 Your Next Steps

Solutions to Exercises

For Further Reading







All of us regularly make mistakes of judgment based on faulty analysis-mistakes as minor as buying the wrong brand of cereal at the grocery and as major as investing a million dollars in a losing enterprise. While some of these errors can be blamed on a lack of information or education, most occur because of the way our minds work. Our minds frequently mislead us, giving us a false understanding of events and circumstances and causing our analysis of events and circumstances to be flawed. In some cases, the consequences can be costly, even deadly.

But we don’t have to passively accept the analytic batting average that nature has given us. By learning about the mental barriers and pitfalls that impede effective analysis and acquiring the skills and techniques to overcome them, our batting average can be improved, and significantly so. That improvement might be the determining factor in a decision that is crucial to personal happiness, professional success, or even life itself. The skills and techniques I speak of are what this book is about: ways of organizing, or structuring, our analysis of problems.

The book explains what it means to structure analysis; identifies and describes the mental traits that tend to lead us astray; explains how structuring our analysis of problems overcomes the ill effects of these traits; describes fourteen easily understood structuring techniques; and provides exercises through which the reader can begin to master them.

Exactly what does structuring one’s analysis mean? The word analysis means separating a problem into its constituent elements. Doing so reduces complex issues to their simplest terms.

One can find countless informative descriptions of this approach in any library. One I find especially appealing is that of the English

philosopher Bertrand Russell, who in 1901 wrote in his classic Principles of Mathematics that, with regard to interpreting the language of philosophic theories, the solution is the analytic method-the breaking down of language until a theory shows itself to be either a set of sensible substatements or just nonsense. In this way, he said, many philosophic “problems” just disappear. Russell’s book changed the way English philosophy was conducted by establishing the “analytic approach” as the only reputable method of studying philosophical questions.

To structure one’s analysis means separating the constituent elements of a problem in an organized way. An example of structuring is the diagram we were taught in elementary school for doing division:

Most of us visualize this diagram when we do division in our heads. Another familiar structuring device is the fearsome IRS Form 1040, which breaks down the process of computing one’s taxes into a manageable, though complex, series of steps. Indeed, we use such devices all the time.

Our normal approaches to analyzing problems are usually adequate for dealing with 90 percent of our problems. It’s the other 10 percent-the big problems, the ones that matter most-where these normal approaches are unlikely to give us a better solution. All of us want to make sound, effective decisions in our professional and private lives, but that’s not easy when the problems we face are complex and manifold. And in the pell-mell pace of modern living, we usually don’t have the time or patience to seek the best solution. The crushing necessity to make the problem “go away now” makes us receptive to any solution that will provide even temporary relief from an oppressive situation. In this pressure-cooker atmosphere it is difficult to fully resolve, much less fully understand, the problems that confront us. We therefore tend to make do with partial solutions that we justify, not altogether incorrectly, as the best we could do under the circumstances.

We settle for partial solutions because our minds simply can’t digest or cope with all of the intricacies of complex problems. We thus tend to oversimplify, hopping from one problem to another like jittery butterflies, alighting briefly and only on those elements we can comprehend and articulate and to which we can confidently assign values and probabilities. Having done so, we are then satisfied to downplay and disregard those elements we do not comprehend and to which cannot confidently assign values or probabilities.

If we are to solve problems, from those confined to i single iiidividual to those afflicting whole nations, we must learn how to identify and break out of restrictive mind-sets and give full, serious consideration to alternative solutions. We must learn how to deal with the compulsions of the human mind that, by defeating objective analysis, close the mind to alternatives. Failure to consider alternatives fully is the most cornmen cause of flawed or incomplete analysis.

In other words, we must learn how to keep an open mind-one of the most difficult things we human beings can do. So any technique we can impose on the mind to force it open is helpful. It should come is no surprise, then, that all of the techniques presented in this book have the effect of opening the mind. The fact is, structuring one’s analysis is the quickest, surest path to opening the mind to alternatives.

Don’t confuse analysis with structuring; they aren’t the same thing. Structuring is to analysis what a blueprint is to building a house. Would you build a house without a blueprint? You could, of course, but there’s no telling what you’d end up with. Building a house, building anythim, without a plan is, to say the least, ill advised. And what structuring is to a blueprint, the techniques of structuring are to a carpenter’s tools-not components of a single, unified system for analyzing problems but an assortment ot techniques that can be used singly or in combination, as a problem requires. And different problems usually require different analytic tools.

By the same token, structuring is like a road map for a trip. Structuring (the road map) shows that the trip has a single beginning but many alternative endings. ‘Where you end up, which alternative path you take, is determined not by the road map but by your analysis and by what you do along the way during the trip.

But other than showing, as Bertrand Russell said, whether the elements of a problem are sensible or nonsensical, what clues structuring-separating elements in an organized way-buy us? l'he answer is a number of things, all of which are necessary for effective problem solving and decision making.*

Some people draw a sharp distinction between problem solving and decision snaking.

Problem solving, they say, focuses on the cause of a problem and on correcting it, while decision making focuses on a specific issue to be resolved. Analytically, I see no real difference between the two. In either case, one must gather information and data to determine the cause or nature of the problem or issue; one must consider alternative options for resolving the problem or issue; and one must evaluate alternative outcomes or consequences of the chosen solution or decision. The analytic process, though not identical, is very similar. In either case, application of analytic structuring techniques facilitates and empowers the process.

First, structuring helps the mind make sense out of complex problems. Most problems, even the ones we regard as fairly simple, are much too complex and ambiguous to analyze without some kind of structuring. I use structuring when I work a jigsaw puzzle. I group pieces of the same or similar color or texture together-the all-blue sky pieces, for example. I then arrange these pieces in subgroups according to their shape. This approach allows my mind to focus on the subgroup of pieces that will most likely fit, eliminating hundreds of alternatives from consideration. Were I not to group the pieces, I would be forced to continually scan the entire field of unused pieces to find the few that are likely candidates. Yet this is exactly how most of us work a problem. We take in the entire problem (the entire puzzle) with all its complex dimensions (all of its pieces) in one gulp and try to digest it. Structuring frees us from this trap.

Second, structuring allows us to compare and weigh one element against another. Instead of looking at a whole bowl of vegetable soup, we look at the soup’s ingredients, one ingredient at a time. This identifies which factors and relationships are critical not only to our analysis but also to the concerns of those who will make use of our findings.

Third, structuring helps us focus our analysis. The mind instinctively focuses. That’s how the mind works, so it’s going to focus whether we want it to or not. Therefore, we’re better off to work with the mind than against it and, in doing so, control what it focuses on. If we don’t, it will do its own focusing, and its shortcuts can lead us down the wrong path.

Fourth, structuring foctise on one ckiisciil it a tune, sslndi, compared to our instinctive scattershot approach of tackling all elements simultaneously, is more systematic, more thorough, and more productive of relevant ideas.

Fifth, by establishing rational, systematic frameworks within which to analyze problems, analytic structuring techniques enable us to impose our analytic will on our subconscious mind, overcoming the instinctive mental traits that lead to faulty or incomplete analysis.

Sixth, all of the structuring methods presented in this book are visual processes that involve writing or depicting elements of a probleiii on paper or on a display board or computer screen, where we can see them. Why is seeing them important? By enabling the brain actually to see the words or numbers or depictions of the problem, we engage more brainpower in analyzing and solving the problem and so gain added insights. Indeed, when elements of a problem are seen visualls, we often discover correlations we missed when we simply thought about them. The old adage-“A picture is worth a thousand words”speaks to the power of engaging the brain’s visual capabilities.

Lastly, structuring allows us to apply our intuition -that mysterious internal sense of knowingto alternative decisions or solutions in an organized way controlled, not by the unconscious mind, but by the conscious. That is why the visual nature of structuring techniques is important, enabling the conscious mind to better focus on, and exercise more control over, the analysis. The effect is to force our intuition into the open, so to speak, where we can consciously cross-examine it and, in doing so, protect ourselves aganist the troublcsoisic niti.iitisc nicntal traits discussed in Chapter 1.

While structuring one’s analysis is alsva s helpful oand sonietmies indispensable, effective decision making and problem solving depends, in the end, not on how we structure our analysis but on the soundness of our thinking, and for that we have to use our mind. But structuring makes that a whole lot easier. Structuring is no substitute for thinking. It is rather a means of facilitating and empowering thinking. Used properly and creatively, structuring techniques will significantly enhance our ability to analyze, understand, and solve problems, lead

1(1 more effective analysis and sounder decisions, and make its feel better about those decisions.

Nowhere else are the methods that are presented in this book taught from such a practical do-it-yourself perspective. What you’re going to learn from reading this book is not theory. These techniques really work. I think you’ll be amazed at their immense potential to open a problem to analysis, and you will wonder, as I did when I first encountered them at the age of forty-nine, why no one told you about them long ago, when you could have applied them to tough problems. I am confident that, if you complete this book, do the exercises, and practice the techniques, you not only will acquire an array of valuable analytic tools but, what I believe is of greater value, you will gain a totally new and enlightened perspective on problem solving.


“The greatest danger in times of turbulence is not turbulence; it is to act with yesterday’s logic”. — Peter Drucker

The shift from manual workers who do as they are being told — either by the task or by the boss — to knowledge workers who have to manage themselves ↓ profoundly challenges social structure

Managing Oneself is a REVOLUTION in human affairs.” … “It also requires an almost 180-degree change in the knowledge workers’ thoughts and actions from what most of us—even of the younger generation—still take for granted as the way to think and the way to act.” …

… “Managing Oneself is based on the very opposite realities: Workers are likely to outlive organizations (and therefore, employers can’t be depended on for designing your life), and the knowledge worker has mobility.” ← in a context




These pages are attention directing tools for navigating a world moving toward unimagined futures.

It’s up to you to figure out what to harvest and calendarize
working something out in time (1915, 1940, 1970 … 2040 … the outer limit of your concern)nobody is going to do it for you.

It may be a step forward to actively reject something (rather than just passively ignoring) and then figure out a coping plan for what you’ve rejected.

Your future is between your ears and our future is between our collective ears — it can’t be otherwise. A site exploration starting point



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