Why Smart People Are Willing to Ask Stupid Questions

“What a stupid question that is. But I watch you a lot, you ask a lot of stupid questions.”

That quote is from Donald Trump chastising reporter Abby Phillip of CNN, when she asked Trump if he wanted new acting Attorney General Matthew Whitaker to rein in special counsel Robert Mueller‘s investigation in 2018. The fact that Trump labeled her question as ‘stupid’ underscores her intellectual firepower.

To understand why, I cite examples from my own experience. A week ago, I was on a phone meeting with two brilliant people. One is a Chief Technical Officer of a cloud company…clearly at the cutting edge of technology. The other is a renowned economist who has held significant positions in the US government. Both possess deep expertise in their respective fields.

It is the smartest people who ask these ‘stupid questions.’ They do not let a conversation move forward without knowing.

Both also belong to professions steeped in acronyms. The tech guru mentioned the acronym ‘SLA’. Now, some of you reading this might not know that SLA means ‘service level agreement’. It defines the level of service expected by a buyer from a vendor. While it is a common acronym in the tech world, it’s not exactly a household word in the world of economics. So, the question came from the economist: “What is an SLA?” 

The quick definition came, and we moved on. That SLA question may be interpreted as ‘stupid’ – by those who are, in fact, ignorant. However it was a clarifying question, so all terms and definitions were understood to ensure a continued and fruitful conversation.

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The point is that it is the smartest people who ask these ‘stupid questions.’ They do not let a conversation move forward without knowing. Because knowledge is powerful and enlightening. Just ask any 3-year old, or 93-year old. Each is likely willing to ask anything.  The fact is, I have found there is one stupid question – “Can I ask a stupid question?” 

Asking that question is based on insecurity. The people who are inquisitive and secure just ask without the preamble. Questions are in fact the lifeblood of what drives humanity to the next level. It also stops us to correct mistakes that can lead to fatal flaws. 

Another friend I am lucky to know is Nicholas Allard. He has an intellectual pedigree that could rival almost anyone’s. He is a Rhodes Scholar, was the administrative assistant and chief of staff to the late Senator Daniel Patrick Moynihan, and staff counsel to the Senate Committee on the judiciary, where he served as legal counsel to the late Senator Edward Kennedy. He also served as Dean (2012-2018) and President (2014-2018) of Brooklyn Law School. From Nicholas, I learned a powerful question: “Why are we doing this?”

But few people have the clarity or guts to ask that question.

Again, there are no stupid questions. But there are people waiting to say your question is stupid just to prop themselves up.

The reason? Most of us are so busy getting the job done that we cannot see the forest for the trees. And we are afraid. What if that question stops an initiative that teams have been working on for years? Or worse yet, what if I am wrong, or get shot down?

Why are we doing this?” is the ultimate whistle-blower question. It is asking those running an initiative if they are making the right decisions. And most of us are afraid to say it. One issue is that we are innately conditioned to obey authority and rank. In fact, corroboration of extreme obedience to authority was shown by a series of social psychology experiments conducted by Yale University psychologist Stanley Milgram. The study was called The Milgram Experiment and is chronicled in his book, Obedience to Authority. 

His experiment revealed that humans are willing to perform acts conflicting with their conscience. The study explained how humans could carry out orders by superiors to commit heinous acts like genocide. It underscores the power of the ‘Why are we doing this’ question.  In society, we also continuously deal with rank, whether it be a caste system or any system of entitlement based on wealth. Asking the tough questions means standing up to authority and asking it to justify the status quo.

Further, in our own work and lives, we have biases. Three of the key biases that cloud our ability to ask tough questions include the following:

• Confirmation bias is when we would like a certain idea or concept to be true and we end up believing it to be true.
• Conformity bias is our tendency to take cues for proper behavior in most contexts from the actions of others rather than exercise our own independent judgment. 
• Authority bias (per Milgram reference above) makes people predisposed to believe authority figures and obey their orders.

They are literally blinders where we do not see what is happening around us. The greatest question right now is “Are we working on the right solutions for COVID-19?” We all wish we had the definitive answer.

This leads me to Nicholas Allard’s follow-up question: “Can we do this better?” If you answer ‘no’, then you have signaled defeat. However, in most cases the question is win-win. It stimulates new ideas and openness to change for the better. 

Again, there are no stupid questions. But there are people waiting to say your question is stupid just to prop themselves up. So, if anyone ever says to you “That was a stupid question”, you now know that to ask it, you overcame fear and bias. Unbeknownst to them, they are paying you the ultimate compliment.

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