Making Sense Of Riddles To Become A Better Problem Solver

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But in another way, riddles can show us something interesting if we can rein in our impatience and only look—not at the riddle but at ourselves and how we are thinking. It’s difficult to maintain this strange perspective—the one in which the focus of our awareness is not the content of the problem itself but the very tools we are using. But it’s essential if we are to ever learn to master and improve these skills.

Riddles may certainly seem overly simplistic on the surface, but this is a virtue if we remember that this simplicity allows us to more easily see the workings of our own minds when we approach such riddles. Sometimes, it takes something seemingly simple and obvious to show us what is actually rather complicated.

Having gone through the riddles in this book, you’ve likely developed your own set of mental schemas, models, and intellectual tools along the way. These are all transferrable skills—if we make the effort to transfer them! Before we conclude this book, let’s consider not only the concrete tools we’ve developed, but practical ways we can use these skills in “real life,” with problems and puzzles you’re likely to encounter every day.

A List of all the Right Questions . . .

If you care about a problem or tricky situation, take the time to unravel and analyze it carefully bit by bit. Don’t assume your brain will always run off and solve it correctly by itself. It may, or you may simply default to bias and lazy habitual thinking, never truly innovating, and never really moving beyond your own conceptual limitations. Whether your problem is a professional, personal, physical, financial, or relational one, the following questions can help activate the skills you’ve learned in this book to more deliberately and consciously solve them. By slowing down, deliberately recruiting our mental tools, and giving ourselves the time to arrive at a considered solution, we make better choices and work our way through difficulties faster. Here are the questions:

Am I seeing all the information here? What do I not know, and most importantly, can I start to even think of the things I don’t even know I don’t know? This constitutes a blind spot, and these are dangerous because you could be running in the opposite direction for all you know. A lay of the land is important first and foremost.

Can I list out my assumptions about this scenario, and then check whether I actually have evidence for each one? How could I find information to fill in these gaps rather than just assuming I already know? This is a question that takes you out of the big picture and forces you to start thinking in smaller steps.

Does this problem look like anything I’ve encountered before? If so, can the solution I used then be used here? Maybe with some adaptations? What kind of past experiences can I draw upon, and how can I also make sure that I don’t get trapped in those same experiences?

Let’s imagine I did find a solution—what would it look like? What form would it take, and what mindset would I likely need to have to discover it?

Can I lay out the premises of the argument I’m looking at? Can I see the logic in the arguments, or is there a flaw that I’ve overlooked? How can I verify this and ensure that I am not being motivated by something other than a pursuit of the truth?

Is it possible that I’m completely off the mark here? Have I debated myself and gone through the thought exercise of trying to prove myself wrong in order to confirm matters?

How many ways can I change my perspective, my attitude, or my focus to see this circumstance differently? Can I imagine the viewpoint of someone else, or a different context that helps me better understand this situation? Whose perspective can I borrow?

What are my expectations here, and are they warranted?

Are the tools that I’m using—my models, theories, or ideas—actually a good fit for my situation? Could it be that the problem is in the tools I’m using? Do I need to take a step back to consider what my true goal is again?

Can I ask better questions here? Even if they’re a bit “out there”? Do I need to think outside the box and look in non-obvious places?

Can I zoom out and look at the bigger picture? What are other people’s motivations, what is the history of this scenario, and what are the contextual clues that will help me see this problem as a whole rather than just a single phenomenon?

What is the quality of the information I’ve gathered? Is it enough? Is it actually true? Are the sources good? What happens when I deliberately seek out information that goes against what I currently believe?

Could I take a step back, “sleep on it,” and return to the problem later?

Is there even a problem at all, or does it just appear to be one because of the perspective I’m taking?

What other dimensions could I understand this problem via? How will the situation evolve over time, for example, or what are some other causes and effects I haven’t considered?

Do I need to do more research, or have I actually done too much already?

Can I look again at all those avenues of enquiry or potential solutions that I’ve written off because they’re “impossible” or don’t make sense (yet)?

How am I using language and symbolism here? Have I mistaken the symbol for something as the thing itself? What happens when I play around with the words or symbols I assign to things?

Considering mistakes I have made in this area in the past, what do I already know about how not to do things?

How would a completely different person solve this problem?

Is the area of the problem I’m considering really the most relevant area, or have I gotten distracted?

Can I just look at this problem without trying to solve it for a second, just with curiosity and the willingness to see it as clearly as I can (knowing that sometimes wanting a particular kind of answer is an expectation and bias in itself)?

Where can I find help, and who can I ask?

Have I asked enough “what if” questions? What do the answers tell me?

Finally, what would my decision process or thinking look like if I removed my ego completely, or if I wasn’t afraid of being wrong?

Becoming a better problem solver and critical thinker is not about being right. If anything, it’s about finding better and better ways to be wrong! It’s far better to “fail” at a task and learn something valuable along the way than to easily understand something right off the bat and never truly know why or how to replicate the process. So, don’t be in too much of a hurry to become a masterful, intelligent thinking machine who vanquishes every problem that emerges! Instead of committing to solving problems, commit to developing the best set of attitudes and critical/analytical skills as you possibly can. In this, you can always be “right.”

“Riddle-Thinking” Applied

Example 1

Problem solving in the real world often cannot be done through simply analyzing information or facts as they are given to you. Companies often face this issue when trying to market their products to an international audience consisting of different cultures. Multinational chains like Starbucks, McDonalds, and KFC often fail to break into specific countries and expand as successfully as they have in the US or western Europe. The following example illustrates how “riddle-thinking” can help companies be more astute.

Imagine a CEO who invests a lot of money into marketing his product internationally, having found immense success locally. He finds the best translators, marketers, and distributors to get the product launched in several countries abroad. Out of four new markets, all do well except one—where the product flops spectacularly and he loses money. He has to figure out why and fix the issue soon or consider withdrawing his presence, as it’s simply costing too much.

The team at the company’s headquarters mull over the reasons it failed. They look at everything they can think of—the local economy, the price point, the market in general, even the political and cultural climate in the country in question. They find nothing to explain the dismal sales. They run through a list of questions much like the one in the previous section, and soon realize there’s something big they’re not seeing. It’s a real riddle!

The problem persisted until the CEO heads to the country himself to see what’s up. Within just a few moments of being in a store that sells his product, he spots the problem. The color of the package design closely matches another completely unrelated product in the store—a muddle that has rather embarrassing connotations for his own product. By being literally in the store that his potential customer is in (i.e. the context), he sees the problem—people are mistaking his product for something else. He goes home, completely changes the design of the product, and soon sees sales pick up in that country.

In this case, no amount of analyzing and mulling over potential strategies would have helped the CEO or his team realize what the problem was. Nor is it possible for them to account for each and every factor that influences the success or failure of a product in a given market.

Ultimately, it turned out that the problem was never with the product itself, but the way it was being perceived due to its similarity to another product. The CEO utilized some divergent thinking to try to account for more localized factors by visiting the country where his product had failed. Since his product succeeded in three of the four markets he had launched it in, he could probably infer that the product itself was not the issue. Instead, it had to be something restricted to the one place where it failed, and the CEO turned out to be right.