Critical Thinking Exercises for People Who Decide for a Living

The forecast in the board pack looked right, everyone nodded, and three months later nobody could remember why they had believed it. Critical thinking exercises are short, repeatable drills that catch that moment: work through one problem a day step by step, keep a weekly log of a decision and what really happened, steelman the option you dislike, and run a premortem before any big commitment.

None of them needs a course. Most take ten minutes, and the best ones attach to work you are already doing, a memo, a meeting, a commute.

This piece sets out eight exercises in three groups, daily, weekly and with a team, with the time each takes and what it trains. It draws on the Foundation for Critical Thinking’s everyday strategies and on Gary Klein’s premortem.

Why Thinking Needs Practice at All

Most executives assume their judgment improves with experience. Some of it does. Much of it hardens instead, into shortcuts that worked once and are never checked again.

Richard Paul and Linda Elder, whose strategies the Foundation for Critical Thinking publishes, make the comparison directly: “Improvement in thinking is like improvement in basketball, in ballet, or in playing the saxophone.” They also warn that changing one’s habits of thought is a long-range project, happening over years rather than weeks. That is an argument for small exercises done often rather than a weekend workshop done once.

The stakes are also higher than they look. Daniel Kahneman won the Nobel prize in economic sciences in 2002 “for having integrated insights from psychological research into economic science”, especially concerning human judgment under uncertainty. A field built around how reliably intelligent people misjudge things is a good reason to practise on purpose.

Critical Thinking Exercises for Every Day

1. A problem a day. This is Paul and Elder’s second strategy. Pick one problem each morning and work it through step by step: state it, say what kind of problem it is, list what you know and do not know, choose a course of action, and adjust once you see what happens. Ten minutes. It trains you to define a problem before solving it, which is where most bad decisions go wrong.

2. Fact or inference. Take the next memo or report you read and mark each claim as either something observed or something concluded. “Sales fell 8% in March” is a fact. “Customers are moving to a competitor” is an inference, and it needs its own evidence. Five minutes. This one is especially useful on board packs, where inferences often arrive dressed as facts.

3. One standard a week. Paul and Elder suggest focusing on a single intellectual standard each week, such as clarity, accuracy or relevance, and watching for it in everything you read and hear. In a clarity week, every time someone says something vague in a meeting, ask for an example. It costs nothing and changes meetings quickly.

These three fit in the gaps of a working day. Our piece on the Andrew Huberman morning routine argues for keeping the first part of the morning clear of email, and a problem a day is a good use of that time.

Exercises for the Week

4. The decision journal. Paul and Elder’s fourth strategy is an intellectual journal: once a week, write about a situation that mattered, how you responded, what was really going on, and what you would do differently. Twenty minutes on a Friday. For an executive the best version is a decision log: what you decided, what you expected, and later, what happened. Our piece on how to remember things quickly explains why the entry has to be written within the hour, before your memory edits it.

5. Steelman the option you dislike. Before you reject a proposal, write the strongest case for it in a paragraph, the case its best advocate would make. Fifteen minutes. If you cannot write it, you do not yet understand what you are rejecting. If you can, you often find one point you had missed.

6. Audit a group pressure. Paul and Elder’s ninth strategy asks you to look at the groups you belong to and name what each requires, forbids and pressures you toward. For an executive the groups are the leadership team, the board, the industry, the people you went to business school with. Pick one a month and ask which of its assumptions you have never tested. They put it bluntly: most people live too much within the view of themselves projected by others.

Exercise	Time	When	What it trains
A problem a day	10 minutes	Each morning	Defining the problem before solving it
Fact or inference	5 minutes	Any memo or report	Spotting conclusions presented as facts
One standard a week	None extra	Every meeting that week	Clarity, accuracy, relevance
Decision journal	20 minutes	Friday	Calibration over time
Steelman	15 minutes	Before rejecting a proposal	Understanding the other side
Group pressure audit	15 minutes	Monthly	Testing inherited assumptions
Premortem	10 to 20 minutes	Before a big commitment	Finding the risk nobody raised
Decision matrix	15 to 30 minutes	Close calls with several options	Making trade-offs visible

Exercises for the Team

7. The premortem. Gary Klein set it out in Harvard Business Review in September 2007, in a piece on performing a project premortem. Team members assume that the project they are planning has just failed and generate plausible reasons for its demise. Ten to twenty minutes, before any big commitment. It works because it gives the doubters in the room permission to speak, and it surfaces risks that a normal “any concerns?” never does.

8. The decision matrix. For a close call with several options, list them, agree the criteria and their weights before anyone scores, then score independently and compare. Our piece on the decision making matrix covers the method step by step. Its value as an exercise is that disagreements about weights come into the open, where they can be argued about.

Run the two together on the decisions that matter. The matrix finds the best option you listed. The premortem asks what you forgot to list.

Where These Exercises Pay Off Most

Irreversible decisions are where critical thinking exercises earn their time. Our piece on Jeff Bezos’s regret minimization framework covers his split between one-way and two-way doors. A premortem and a steelman on every one-way door is a cheap insurance policy.

Money decisions come next. Choosing between accounts, as in our piece on a Roth IRA vs brokerage account, or reading a new compensation package, is mostly fact-or-inference work: what is guaranteed, and what is somebody’s projection?

Benchmarks are a good place to practise. Our guide to net worth by age shows how an average can mislead, and asking what a number leaves out is the same skill as the fact-or-inference drill.

Selling a company is the biggest test most owners face. Our piece on how to sell a small business lists the questions a buyer asks, and running a premortem on your own sale two years out is one of the best uses of an afternoon.

Education choices are another. Before committing to an executive MBA, steelman the case against it, and write one sentence on what will be different three years after you finish.

Three Mistakes That Waste the Practice

The first mistake is practising only on easy material. Running a premortem on a project everyone already doubts tells you nothing new. The exercises earn their time on the plans you are most confident about, because that is where the blind spots sit. If a drill never changes your mind, choose harder targets.

The second is doing the exercise in your head. A steelman you only think about tends to be a weak one, because the mind quietly skips the uncomfortable parts. Writing it down forces each step into the open. The same goes for the problem a day: a written definition of the problem is far harder to fudge than a mental one, and it gives you something to check a week later.

The third is treating the exercises as a private hobby. The decision journal is most useful when you go back to it. Once a quarter, read the entries from three months ago and mark each one: did it play out as you expected, better or worse? The pattern across a dozen entries tells you whether you tend to be too optimistic about timelines, too pessimistic about people, or too slow to cut losses. That pattern is worth more than any single exercise.

A related trap is mistaking speed for skill. Many senior people are rewarded for deciding fast, and the habit carries over into these drills. Rushing a problem a day in two minutes defeats its purpose. The exercise exists to slow one decision down on purpose, so that the steps you normally skip become visible. Speed comes back on its own once the steps are habits.

Finally, keep the drills separate from performance reviews. If people think a premortem will be used against them, they will list safe, harmless risks. The exercise only works where saying “this could fail because of my own part of it” carries no penalty, and setting that tone is the leader’s job.

Fitting Them Into a Full Diary

Do not try all eight at once. Pick one daily exercise and one weekly one, and put them in your productivity plan as fixed blocks for a month. Add a third only when the first two run without effort.

Protect the time when you think best. As we noted in our piece on Jeff Bezos’s morning routine, he puts his hard decisions before lunch, and the same logic applies to practice: do the problem a day early, not at the end of a draining afternoon.

Expect the exercises to feel uncomfortable at first. Steelmanning an idea you dislike, or hearing a premortem pick apart your plan, raises the pulse. Our piece on stress tolerance covers how that kind of small, chosen discomfort builds capacity over time.

Reading helps, as long as it is slow. Some of the Warren Buffett books and Bill Gates book recommendations we covered this week are, in effect, long records of people checking their own reasoning.

And if you want a public version, write it down. Our guide on what to post on LinkedIn recommends posting a decision and its reasoning, which is a decision journal entry with an audience. Having to explain your thinking to strangers is a strong exercise in its own right.

Frequently Asked Questions

What are good critical thinking exercises for adults at work?

Four that fit a working week: work through one problem a day step by step, mark each claim in a report as fact or inference, keep a weekly decision journal, and run a premortem before big commitments. Each takes between five and twenty minutes and attaches to work you are already doing.

How long does it take to improve critical thinking?

Longer than most people expect. Richard Paul and Linda Elder describe changing one’s habits of thought as a long-range project that happens over years rather than weeks. Small exercises done every day add up faster than an occasional course.

What is a premortem?

A team exercise described by Gary Klein in Harvard Business Review in 2007. Before starting a project, the team imagines it has already failed and lists plausible reasons why. It brings out risks that people are reluctant to raise in an ordinary planning meeting.

Thinking well is a skill that responds to practice like any other. Ten minutes a day spent defining one problem properly will do more for an executive’s judgment than a year of reading about how others think.