15 Critical Thinking Strategies to Solve Your Hardest Problems

Life is filled with puzzles and challenging problems that require you to look at things from a different perspective. We often find ourselves ‘stuck’ on a problem because of a failure of viewpoint. These fifteen critical thinking strategies will help you to reexamine these problems with a fresh look, whether they are logical puzzles, interpersonal difficulties, or challenging situations that you find yourself in.

(1) The Paradox Strategy

React to the problem in the opposite of what is expected. Treat difficult things as though easy, and easy things as difficult.

• Does this situation feel stressful? Treat it as rather unimportant. 
• Does it seem unimportant to most people? View every detail as significant. 
• Do others expect you to adopt a serious tone? Be lighthearted. 
• Do others treat the subject glibly? Impress them with your seriousness.

Example: Warfare is the perfect example of a situation where everyone involved is nervous and intense. The great leader inspires confidence and good thinking when he acts with calmness and projects confidence in the victory of his side.

Question to Ask: How would most people react in this situation, and how can I do the opposite?

(2) The Reversal Strategy

Turn the problem upside down. If everyone focuses on the beginning of the problem, work backward from the end. If everyone is focused on the ending, look closely at the beginning. When it’s hard or challenging to solve, most people fail to solve it. You can succeed by doing it differently than most people. Look at the problem in reverse.

Example: This is a common way to solve algebra problems. For example, in the problem ‘3x – 7 = 14,’ the normal way to find the value of ‘x’ is to rearrange the problem in such a way that ‘x = (14 + 7) / 3’.

Question to Ask: What other starting point could I use?

(3) The 80/20 Strategy

Find and isolate the 20 percent that matters, then put all your effort into that piece of the puzzle. To do this, you must ask and answer several crucial questions: What is the 20 percent? What does it look like to focus your energy on the 20%? How do you avoid wasting time on the 80%?

Example: 80% of a company’s profit often comes from 20% of the merchandise. A business can often increase profits by finding that 20% and marketing it more widely, rather than trying to increase sales from the remaining, and less successful, 80%.

Question to Ask: What is the 20% and how do I prioritize it?

(4) The One Percent Strategy

If you wish to create massive improvement, don’t try to overhaul the entire system. Instead, aim to improve efficiency by one percent in every discrete part. A one percent improvement across every aspect of the system will lead to many percentage points of improvement throughout.

Example: In ‘Atomic Habits,’ author James Clear references a bike team that was able to consistently win when their couch began focusing on 1% improvements. They did this by reducing drag by one percent with more form-fitting clothing, improving cycling technique by one percent, and so on. These small adjustments ultimately produced significant improvements for the team.

Question to Ask: Where can I make small improvements?

(5) The Skeptic Strategy

“In all affairs, it’s a healthy thing now and then to hang a question mark on the things you have long taken for granted” (Bertrand Russell). Isolate and interrogate every presupposition you have. What do you assume and take for granted? Might you be wrong in something that you assume is rock-solid?

Example: The movie ‘Midway’ (2019) dramatizes the failure of the Japanese to utilize this strategy. Although they had an excellent battle strategy, they assumed it was impossible for the American fleet to be in a certain position. Their failure to doubt this assumption led to a massive strategic defeat.

Question to Ask: Could I be wrong about that?

(6) The Alternate Perspective Strategy

What would you be thinking if you were sitting across the table from yourself? Try to place yourself in the mind of the other person and think what they are thinking.

Example: In ‘Superforecasters,’ Annie Duke, a professional poker player, explains this idea simply. Most poker players assume that if someone raises the bet, they have a strong hand. Duke helps players to see the table from the perspective of their opponent. If you have a really strong hand, you are less likely to raise the bet, since you don’t want to scare everyone. You want as much money in the pot as possible. It’s a simple idea, but few people realize it, because they fail to see from the perspective of the other side.

Question to Ask: If roles were reversed, what would I do?

(7) The Process Strategy

Switch your focus from the outcome and focus primarily on the process. Rather than trying to solve this problem, what skills and habits do you need to develop that will generally lead to finding answers to these problems? A good process is better than a good outcome.

Example: In ‘Tribe of Mentors,’ chess Grandmaster Maurice Ashley refers to a time when he lost a game of chess in his quest to be a Grandmaster. Alexander Shabalov pointed out the mistake he made, then said “In order to become a Grandmaster, you must already be one.” This was transformative for Ashley, and he realized that if he were to ever win the title, he must focus not on winning a specific game, but on becoming better. This ultimately led to him attaining the title.

Question to Ask: What habit do I need that would make this type of problem disappear?

(8) The Level-Up Strategy

Shift to thinking on a different level. You may need to look at the problem in more granular detail. You may need to look at the problem from a more overarching perspective.

Example: A manager once told me about an employee who was generally very easy to work with and kind to coworkers, but suddenly started to have problems working with the rest of the staff. Discussion with the manager revealed that she was going through a difficult personal situation. These sorts of stories are common in management. Often, the problem is not the ‘problem itself.’ There are often bigger factors at play. These things must be dealt with within a recognition of the bigger picture, not just the specific problem behavior.

Question to Ask: What other levels are there to this problem?

(9) The Bottleneck Strategy

Get a clear understanding of the exact point where the problem is occurring, then focus on solving that particular problem. This strategy understands the problem point may be the single issue that is slowing down everything else.

Example: A factory production line will only be as fast as the single slowest point on the line. To improve efficiency, find the slowest point and improve its speed.

Question to Ask: Where exactly is the problem?

(10) The Ignoring Strategy

Is this actually a problem, or would it resolve itself on its own? James Clear, author of Atomic Habits, says, “Some things are better off ignored than attacked. Attention is the oxygen of conflict. When you fight a problem, you breathe life into it. When you starve a problem of your attention, you suffocate it. In a surprising number of cases, the way to solve a problem is to ignore it.” 

Example: Criticism and hate mail are often better ignored than answered. Answers rarely fix the problem, they just throw fuel on the fire and waste valuable resources. Ignoring such negativity sometimes is enough to make it go away.

Question to Ask: What’s the worst that happens if I don’t do anything?

(11) The Movement Strategy

Beware of the curse of knowledge. Sometimes you feel stuck because you don’t have total information, but good decisions and actions are rarely taken with complete knowledge. Sometimes solving problems takes movement and action to find clarity. This is a key lesson of the OODA loop. 

Read more about the OODA loop from a previous post here.

Example: A fighter jet that is flying straight and level may not realize that it is being chased by an enemy fighter. By turning, rotating, and varying its flight path, it is more likely to visualize the enemy. This is a better strategy than continuing to stay in the same flight path and waiting for the enemy to show up.

Question to Ask: What positive action can I take that might lead to more information?

(12) The Initiative Strategy

How can you take charge of the problem? How do you step in with a bold and unexpected action, which throws the problem ‘off balance’ so that you can take the initiative? You may feel that you have no choice but to sit back and wait, but sometimes a dramatic action can turn events in your favor.

Example: Once, while playing a game of paintball, I waited for the ‘enemy’ to approach my highly defensive position. They didn’t come for some time, so I decided to seize the initiative. I ran full-speed in the direction that I assumed they would come. Sure enough, three of them were already getting into position, waiting to storm my defense. However, because I took the initiative, they were caught off guard and all three made easy, unprepared targets.

Question to Ask: What bold move could I make that might be unexpected, but regains the initiative?

(13) The Construction Strategy

Take it apart the same way you put it together, or put it together the same way that you took it apart. Reverse the lessons that you learned from doing the opposite.

Example: The IT sector does this all the time. Rather than focusing just on improving a system’s security, they try to hack their own system. This reveals the weaknesses and vulnerabilities of the system so that they can then go in and fix the problems.

Question to Ask: How would I (or did I) do the opposite?

(14) The Simplification Strategy

Sometimes the answer is more simple than you expect. Sometimes there is no complicated and elegant solution. You can overthink the problem, assuming that the easy solution is too inelegant to be right. Beware: the more intellectual someone is, the more they will be drawn to an elegant or philosophical solution rather than a simple ‘fix’ or ‘patch’ that may solve the problem. This is a unique danger of the philosopher’s mind rather than the mechanic’s mind.

Example: I was once trying to put together a widget brain puzzle. This puzzle involved several pieces that were supposed to fit together and make an object. Despite spending a significant amount of time playing with it, I couldn’t make sense of the puzzle. Early on, I came up with a possible solution, but it involved me pushing the pieces together with more force than I assumed was needed. After giving up, I learned that the puzzle is solved in that exact way but because it seemed like a rather crude solution (rather than a philosophically appealing solution where everything fit perfectly), I missed the solution.

Question to Ask: Is there a simple, crude, or ‘patchy’ way to solve this problem?

(15) The Observation Strategy

Play with the individual pieces and make observations. What is the same; what is different? Focus not on a solution, but on making every possible observation. You can use these observations to question your assumptions (#5 – The Skeptic Strategy). Sometimes you just need extensive time observing the data and less time analyzing it, which will yield more data to analyze in the future.

Example: In the corporate world, I’ve heard of individuals who are hired by companies to try to solve the problems in the company. One effective strategy that is sometimes used is that they simply sit in every meeting and become the ‘fly on the wall’ constantly. They make no recommendations and don’t try to solve the problem for a significant period of time. They simply observe everything, until they finally have enough data to identify the issue.

Question to Ask: What other observations can I make about this problem?

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