A simple tip that makes you a better professional

Yogesh Upadhyaya
5 min readApr 8, 2023

How quickly can you solve this simple case? A coastal habitat of twenty thousand households faces a challenge. The people of the habitat rely on groundwater and overdrawing has allowed sea water to seep in thereby increasing its salt concentration. There is a proposal to purify the brackish water using a very cool technology from a top notch science institute. The big question for the project team is whether to put up one big plant or ten small plants. One big plant would be easier to maintain. Ten small plants would mean redundancy. Which is the better alternative? If you cannot decide, at least make a list of any additional information you need to make the decision.

German Stamp on Emperor’s New Clothes from Wikimedia Commons

When I presented this case to a bunch of students, it took more than 20 questions before someone asked, ‘Would the project provide water only for drinking or for all domestic use?’ Once the question was asked, it was obvious to everyone that this should have been the first one. Both the quantity and quality of the output of the plant depend on this. This question should definitely have been asked before esoteric questions about technology for example. This kind of thing happens in work settings all the time: People don’t ask the most basic questions. Why does this happen? Why did my class not ask this question early? The answers to these questions may be useful for young professionals.

Part of the challenge for my students was the way I framed it. I said that they had to decide between one large project and ten small ones. I suggested that a quick response would be a sign of their smartness. And I razzle dazzled them with talk of technology. However, I believe that there was another strong underlying reason: We don’t ask the most basic questions because we don’t want to look foolish in front of others. In fact, we resist looking foolish even when there is no one else around.

There is a folk table about this — Emperor’s New Clothes. Two swindlers take a lot of money from an emperor and promise to make him a suit from magical cloth that would be invisible to anyone who was stupid or incompetent. Many officials are sent by the emperor to check the progress and they all report that the suit is coming along nicely even when they see nothing. The officials feared that if they say they saw nothing, everyone would know that they are stupid. Finally on the big day, the emperor wears the non existent clothes and goes on parade in front of the people. Everyone in the crowd pretends to be able to see the emperor’s clothes until a child points out that the emperor is buck naked and the spell breaks.

There is a reason that the centuries old folk tale is enduring. The fear of looking foolish is universal. Moreover, this fear is not totally unjustified. While sometimes, we may be the ones pointing out that the emperor is not wearing clothes. Other times our questions may actually be stupid. The probability of the latter happening is higher in a new job or a new situation. Just because we know that we are afraid of looking stupid does not mean that our questions aren’t stupid! So how can we overcome our fear of being stupid when there is a chance that we are being stupid?

First, be comfortable looking stupid once in a while. There is a lot of learning on the other side of stupidity. To make your task easier, declare your stupidity upfront! Begin your question with a variation of,

‘This is probably a stupid question, but ….’.

This is such a powerful technique that it is worthwhile listing out some variations.

‘Maybe everyone else already knows this, but could you tell me…’

‘I know I am supposed to know this, but…” And my favorite,

“Even though this discussion is very advanced, can I ask a Kindergarten (KG) level question…’

‘KG level’ questions protect us from embarrassment while allowing us to clear fundamental doubts. If we are the ones being stupid, then the answer would help us learn. If everyone in the room was not clear about the basics, then we have probably saved everyone a lot of time. It is a win win. Almost.

There are two challenges associated with ‘KG level’ questions. First, when it turns out that the ‘basic’ question has not been thought of by anyone, it is very embarrassing for everyone. If you do this to a room full of senior people and experts, nobody will like you. Your career could suffer. The second problem is that pointing out that the emperor is not wearing clothes is addictive. I should know. Too many times, I have taken a childish delight in asking KG level questions even when I knew that the other side was going to look stupid. You can mitigate these challenges with the right intent.

Ask KG level questions with an intention to learn and not with an intention to crow over the experts (however tempting it may be). Ask with genuine humility. Think twice before doing it in front of many people if there is a choice of asking in a smaller group later. Most of all, don’t break into a bhangda if you have shown that the emperor has no clothes.

In projects like the one I discussed at the beginning of this piece, it is possible that a few weeks pass before the team gets around to asking whether they need to provide quantity and quality of water for drinking or for bathing and other needs. Someone asking basic questions can help the team a lot. Asking KG level questions is a superpower. But it comes with its own kryptonite. Use it wisely.

What is your story of asking a KG level question? Do comment.

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This article is a part of a series The Thinker’s Toolbox. Do click to see related content.



Yogesh Upadhyaya

Entrepreneur. Economist. Investor. Actor. Technophile. Policy wonk. Comedian. I love to explore places where these worlds intersect.