Seven Habits of Highly Critical Thinkers

Dr. Tim Van Gelder. 2013.

Some people excel at critical thinking; others, not so much. Scientist Carl Sagan and investor
Charlie Munger are oft-mentioned exemplars; my friend and colleague Paul Monk is less famous
but also impressively sharp. On the other side we have… well, Homer Simpson can stand in for
all those it would be rude to name.

But what makes a thinker more highly critical than others? And how can any person lift their
game? This can be explored through the notion of habits. Highly critical thinkers have developed
many habits which help them think more effectively. With sufficient commitment and patience,
and perhaps a little coaching, such habits can be acquired by the rest of us.

This post describes seven major habits of highly critical thinkers. The list is obviously inspired
by the hugely successful book about highly effective people. Whatever one might think of that
book, if a similar exercise for critical thinking could have even a tiny fraction of its impact, it
would be well worth undertaking.
Everybody is familiar with the term “critical thinking,” and has a reasonable working sense of
what it is, but there is much disagreement about its proper definition. There’s no need to enter
that quagmire here. Suffice to say that critical thinking, for current purposes, is truth-conducive
thinking, i.e., thinking that leads to correct or accurate judgements. It is, in a phrase I like to
use, the art of being right – or at least, of being more right more often.

But what kind of thinking conduces to truth? What is this subtle art? Back in the early
seventeenth century, the philosopher Francis Bacon characterised it this way:

For myself, I found that I was fitted for nothing so well as for the study of Truth; as having a
mind nimble and versatile enough to catch the resemblances of things … and at the same time
steady enough to fix and distinguish their subtler differences; as being gifted by nature with
desire to seek, patience to doubt, fondness to meditate, slowness to assert, readiness to
consider, carefulness to dispose and set in order; and as being a man that neither affects what is
new nor admires what is old, and that hates every kind of imposture.

Four hundred years later, political scientist Philip Tetlock conducted extensive and rigorous
studies of hundreds of experts in the political arena, focusing on their ability to forecast.
He found that the experts fell into two main groups:

One group of experts tended to use one analytical tool in many different domains; they
preferred keeping their analysis simple and elegant by minimizing “distractions.” These experts
zeroed in on only essential information, and they were unusually confident—they were far more
likely to say something is “certain” or “impossible.” In explaining their forecasts, they often built
up a lot of intellectual momentum in favor of their preferred conclusions. For instance, they were
more likely to say “moreover” than “however.”

The other lot used a wide assortment of analytical tools, sought out information from diverse
sources, were comfortable with complexity and uncertainty, and were much less sure of
 themselves—they tended to talk in terms of possibilities and probabilities and were often happy
to say “maybe.” In explaining their forecasts, they frequently shifted intellectual gears,
sprinkling their speech with transition markers such as “although,” “but,” and “however.”

The second group, the “foxes,” were better forecasters than the first, the “hedgehogs.” Foxy
thinking, it seems, is more truth-conducive than hedgehoggery.

Two points jump out from these quotes. First, the two accounts have much in common,
underneath the differences in style. The essence of critical thinking is largely stable across the
centuries.

Second, they are both describing what good thinkers tend to do. Theorists of critical thinking
have various ways of thinking about these tendencies; some talk of dispositions, others of
virtues. Here I take what may be a novel approach and consider them as acquirable habits.

A habit is just a propensity to take actions of a certain kind in a relatively automatic or reflexive
manner. And as we all know, and as elaborated in the recent book by Charles Duhigg, The Power
of Habit, good habits can be cultivated, and bad habits overcome. So the goal here is to list:
• propensities to do things of certain kinds more or less automatically under appropriate
circumstances; which propensities are
• possessed by highly critical thinkers much more often than by ordinary folk, and which
• help them to make more correct or accurate judgements, and
• could be picked up, or further developed, by any ordinary person with a reasonable amount
of effort; with the result that
• they would themselves become more critical.

The habits described below are the kinds of things highly critical thinkers really do do. They are
not merely prescriptions or guidelines which would help anyone to be more critical if anyone
were disciplined or virtuous enough to follow them.

To illustrate: Blogger Shane Parrish reports that a hedge fund manager and author, Michael
Maubousson, asked the Nobel-winning psychologist Daniel Kahneman what a person should do
to improve their thinking. “Kahneman replied, almost without hesitation, that you should go
down to the local drugstore and buy a very cheap notebook and start keeping track of your
decisions.”
Now, it is plausible that keeping track of your decisions in a notebook would improve your
thinking. However, it is not a habit of highly critical thinkers, at least in my experience. I don’t
recall ever observing a highly critical thinker doing it, or hearing one say they do it. I don’t even
do it myself, even after hearing the great Laureate’s advice (and apparently Maubousson doesn’t
either).

And so to the habits themselves.

1. Judge judiciously
One of the most salient thinking traps is, in the common phrase, jumping to conclusions. Highly
critical thinkers have cultivated four main habits which help them avoid this.
First, they tend to delay forming a judgement until the issue, and the considerations relevant to
it, have been adequately explored, and also until any hot emotions have settled (Bacon’s
“slowness to assert”).

Second, they tend to abstain altogether from making any judgement, where there are
insufficient grounds to decide one way or another. They feel comfortable saying, or thinking, “I
don’t know.”

Third, when they do make a judgement, they will treat it as a matter of degree, or assign a level
of confidence to it, avoiding treating any non-trivial issue as totally certain.

And fourth, they treat their judgements as provisional, i.e., made on the basis of the evidence
and arguments available at the time, and open to revision if and when new considerations arise.

2. Question the questionable

Much more often than ordinary folk, highly critical thinkers question or challenge what is
generally accepted or assumed. Sometimes they question the “known knowns” – the claims or
positions which constitute widely-appreciated truths. Other times, they target the implicit, the
invisible, the unwittingly assumed.

Highly critical thinkers do not of course question everything. They are not “radical skeptics”
doubting all propositions (as if this was even possible anywhere other than in philosophical
speculation). Rather, they tend to be selective or strategic in their questioning, targeting claims
or positions that are worth challenging, whether in some practical or intellectual sense. They are
skilled in identifying or “sniffing out” the “questionable,” i.e. claims which are potentially
vulnerable, and whose rejection may have important or useful implications.

3. Chase challenges
We all know that feeling of instant irritation or indignation when somebody dares to suggest we
might be wrong about something. Highly critical thinkers have cultivated various habits
counteracting this reaction – habits which actually lead to them being challenged more often,
and benefiting more from those challenges.

For example, while we mostly seek and enjoy the company of those who share our views, highly
critical thinkers make an effort to engage those of a contrary opinion, tactfully eliciting their
objections. And when fielding such challenges, highly critical thinkers resist the instinct to
ignore, reject or rebut. They will be found doing such seemingly perverse things as rephrasing
the objections to be sure of understanding them, or even to render them even more powerful.
Charlie Munger is quoted as saying “I never allow myself to have an opinion on anything that I
don’t know the other side’s argument better than they do.”

Another habit of highly critical thinkers is reading widely, and especially reading from sources
likely to present good quality contrary views and arguments. Finding themselves drawn to a
position (e.g., that William Shakespeare of Stratford was unlikely to have been the author of the
works attributed to him) highly critical thinkers seek out the best presentations of the orthodox
position. In short, they strive to test or “prove” their views, rather than support or defend them.

4. Ascertain alternatives
Highly critical thinkers are always mindful that what they see before them may not be all there
is. They habitually ask questions like: what other options are there? What have we missed? As
opposed to/compared with what? They want to see the full range of relevant alternatives before
passing judgement.

For example, when considering a difficult decision, they put extra effort into searching for – or
creating – courses of action outside the standard, provided or obvious ranges. When trying to
explain why something happened, they will allocated more time than most people do to
expanding the range of hypotheses under consideration. In a negotiation, they seek to develop
new, mutually acceptable solutions rather than “horse-trading” on existing positions.

5. Make use of methods

When considering a course of action, a critical thinker of my acquaintance, who happened to be
successful banker and company director, said she always asked herself two simple questions:
(1) what’s the worst thing that could happen here? and (2) what’s the best thing that could
happen? The first question prompts us to search for potential drawbacks a bit more thoroughly
than we might otherwise have done. The routine amounts to a rudimentary (or “fast and frugal”)
risk analysis.

This example illustrates how highly critical thinkers habitually deploy suitable methods to
structure their thinking and improve the conclusions. Another example: in psychology
department colloquiua I used to attend, participants, after hearing a colleague present their
work, would reflexively use a method I call scenario testing. This involves diligently and
creatively searching for scenarios in which their colleague’s conclusions are false, even though
their premises (data) are true. To the extent that plausible scenarios of this kind can be
identified, the inferences from the premises to the conclusions are suspect.

There are literally scores of methods one might use. Some, like the rudimentary risk analysis
mentioned above, are simple and informal, and can be quickly learned and exploited by almost
anyone. Others are elaborate, technical and may require specialist training (e.g.,
rigorous argument mapping, or full quantitative risk analysis). Generally, the more sophisticated
the method, the less widely it is used, even by the most highly critical thinkers. Every such
thinker has built up their own repertoire of methods. What’s most important is not so much their
particular selection, but the fact that they habitually deploy a wider range of methods, more
often, than ordinary folk.

6. Take various viewpoints

Highly critical thinkers well understand that their view of a situation is unique, partial and
biased, no matter how clear, compelling and objective it seems. They understand that there will
always be other perspectives, which may reveal important aspects of the situation.

Of course, most people appreciate these points to some degree. The difference is that highly
critical thinkers are especially keen to profit from a more complete understanding, and so have
cultivated various habits of actually occupying, as best they can, those other viewpoints, so as to
see for themselves what additional insights can be gained.

One such habit is trying to “stand in the shoes” of a person with whom we may have some
conflict, or are inclined to criticise. Another is to adopt the persona of a person, perhaps a
hypothetical person, who strongly disagrees with your views, and to argue against yourself as
strongly as they would. A third (relatively rare) is to take the perspective of your future self,
having found out that your current position turned out to be wholly, and perhaps disastrously,
wrong. What do you see, from the future, that you are missing now?

7. Sideline the self

People tend to be emotionally attached to views. Core beliefs, such as provided by religions or
ideologies, help provide identity, and the comforts of clarity and certainty. Sometimes pride
binds us to positions; having publicly avowed and defended them previously, it would be
humiliating to concede we were wrong. Highly critical thinkers have habits which help to sever
these emotional bonds between self and beliefs, allowing the thinker to discard or modify beliefs
as indifferently as a used car dealer will trade vehicles. Highly critical thinkers have in other
words learned how to sideline the self, removing it from the field of epistemic play.

One habit is to avoid verbally identifying oneself with positions by using distancing locutions.
Instead of saying things like “Its obvious to me that…” they will say things like “one plausible
position is that”. A similar technique is to give positions names. Instead of boldly asserting that
Shakespeare must have written the works, publicly committing yourself to this view, say
“According to the Stratfordian view…”.