How playing dumb makes you smarter

Common: Taking the initial and/or frequent comments as the whole truth and consequently being led astray.

Uncommon: Live long enough and you’ll likely agree there is A LOT of misinformation and misaligned incentives in this place we call the ‘real world.’ Sometimes intentions are malicious, other times it’s ignorance, and sometimes it’s a matter of stretching the truth.

But let’s drop the finger. If we’re honest, we can all admit to being guilty of pretending to have the answer or backing our sentiments with baseless confidence.

Why? No one likes to be wrong. This predisposition is hard wired within us, so let’s explore a solution that helps improve our own intellectual prowess while simultaneously identifying half-truths and making course corrections.

The inability to remove the husk from the kernels of feedback, advice, and information we receive each day prevents us from achieving real success in our personal lives, relationships, and professional lives. There are several ways to extract facts from a soupy sea of fiction, but one of the most effective, benevolent ways to do this is by playing dumb.

Smart detectives play dumb

Of the countless non-fiction books and biographies I’ve read about powerful leaders, I’ve noticed a trend that is often glossed over: Successful people are excellent, but also sly, detectives. We overlook this because we slap an over-simplified label on the ability to make good critical decisions. Yes, there’s more to it than mere ‘intuition.’

Socrates, Einstein, Mother Teresa, JFK, Peter Drucker, and thousands more were very well known for their penetrating use of questions.


Another great example is Steve Jobs, who was often recognized for his ability to make insightful, high-risk, high-stakes decisions. Throughout his biography, the author cites many meetings and crucial encounters with members of team and his competition. This is not overtly identified by the author, but it is a recurring theme: Jobs was relentless in asking questions — but not necessarily the creative, cunning, and deep intellectual questions you would expect.

Many of his questions were so painfully obvious they initially stumped the people being asked the question.  When Jobs sat waiting and listening intensely instead of elaborating, an interesting phenomena occurred… the person or group began coughing up their core assumptions behind their conclusion, outcome, or position on the subject. When Jobs proceeded with more simple questions such as, “But why” and making statements such as “Can you please explain what you mean?” he was able to reveal (to himself and the speaker) small, but significant pieces of information that helped him make critical course corrections.

Helping people be more truthful

People prefer to avoid complication and especially confrontation. Thus, it’s often a natural tendency to oversimplify or unconsciously ignore information that’s difficult to process or that might illicit a negative response from the listener. But in business and in all personal relationships, this behavior can be fatal.  In these instances asking piercing and discerning questions can reveal buried truths.

“But asking such potent questions takes years of practice to master,” you say. Yes, it certainly does.

We should always work on developing these investigative abilities, but there is another, often equally effective and underrated path to revelation, which is – you guessed it – pressing upon the obvious.  This is, in essence, what it means to play dumb.

How to play dumb the smart way

Playing dumb gives us the opportunity to ask these candid questions without being too aggressive, patronizing, or disrespectful.  Any good business person and generally happy individual will like agree: Good questions trump easy answers.  Always.

So how can you make an art of playing dumb?  It’s a 4-tiered process:

  1. Start by setting aside preconceived notions – This is less uncommonly known as Shoshin or beginner’s mind. “It refers to having an attitude of openness, eagerness, and lack of preconceptions when studying a subject, even when studying at an advanced level…”
  2. Slowly start to re-identify the assumptions at hand. You may ask yourself, “What assumption would support this/that statement or action or even this conversation or meeting?”
  3. Ask extremely simple questions of others. The simpler, the better (examples below).
  4. Repeat step 3. The more you ask someone the same question, the greater the chance the response will change.

Some simple, but practical questions

Contrary to what most people believe, effective conversations, meetings, and strategy sessions are not about answering questions; they are about asking questions.


Here are some sample questions you may find useful:

  • Why?
  • Why not?
  • Why is this important?
  • Why do we consider this the right/best way/answer?
  • What do you mean?
  • But what are you/we really trying to accomplish here?
  • Can you please rephrase that?
  • Can you tell me more?
  • Can you please summarize it one more time?
  • Could you please explain the idea using a different metaphor and/or set of terms?
  • How do you figure? OR Why do you think that?
  • Why does this appear obvious to you?
  • Why is this surprising?
  • Is this the best you/we can do? OR Is there room for further improvement?
  • Why did you come to that conclusion?
  • What would you most like me to know/understand?
  • Why is this time different?

Curiosity is the keel of truth

All great leaders ask great questions. They reveal introverted truths that allow them to make better quality decisions.

And this does not need to be a complicated process. It’s really a matter of probing the most evident presumptions at hand.

Still confused? Model a child. Just think of the last instance you spent time with a curious child. They likely asked the same banal questions again and again. But in doing so (if you’re brave enough to admit it) you likely found yourself questioning your own knowledge on the subject.  This is because painfully obvious questions start to dismantle the most basic, foundational assumptions – and these assumptions are the glue that tie the real facts together. When these start to crumble, only truth remains.

And the more truth we have to draw from, the better our lives will be. I’m sure you’ll agree.

Your thoughts?

Have you had success with this concept before?  Do you agree or disagree? Share your thoughts below…

Stay uncommon,

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