Willingness to look stupid

"Discovery is the privilege of the child: the child who has no fear of being once again wrong, of looking like an idiot, of not being serious, of not doing things like everyone else." — Alexander Grothendieck

I think Dan is on point here with asking questions for true understanding and not being afraid to do that. Our society, unfortunately, for the most part rewards those who are confident and act like they know everything instead of those who admit they don't know something. And being willing to look dumb/bad is crucial to learning a language, instrument, or new hobby well...

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But he lost me with the examples of the Apple computer box. Employees aren't little robots- they're actual humans that (mostly) are trying to be helpful. It would've taken Dan -significantly- less time and effort to just say WHY he was looking for a smaller box. Probably the same deal with the auto insurance agent- he could've just explained WHY he wanted such an unusual request, and the agent likely wouldn't have incredulously asked him 3 times.

In my experience people are straightforward and respectful with you when you're straightforward and respectful with them. Waltzing in and going "give me the thing in the smallest box" makes absolutely zero sense and it's like Dan was just purposefully playing a game of being obtuse towards random help staff... People aren't intelligent or stupid because they get confused when someone comes in with very unusual requests that they refuse to elaborate on.

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Also, I truly don't get the box thing. Technology-wise it makes no sense. Why doesn't Dan explain the reason in this post either?

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Last edit: I had an unusual situation once in Seoul at this one cafe that I visited a lot. There were two registers, and for some reason my credit card just wouldn’t work on the left register. So a few times I just asked “Hey, this is an unusual request, but could we use the machine on the right? My card works on that one, but not this one.” And guess what? The employees went “oh, ok” or “sure”.

It took slightly more effort on my part than saying “hey, use the machine on the right”. But then nobody was confused. It had nothing to do with the employees being intelligent or stupid or being perceived as such.

Dan Luu interprets confusion from his lack of explanation as people thinking he is stupid. It almost seems the other way around, Dan Luu is the one who thinks other people are stupid (Apple Store clerk, insurance salesperson) because they don't know what he knows.

I try to lead by example on this one - particularly in front of customers or other junior team members. There is a huge hazard in training people to avoid looking like they are doing the wrong thing. Most of our struggle today is extracting useful information from the business so we can deliver a properly-configured product to them. You don't want anyone to feel like they are being persecuted for not knowing something or you will not be able to get much worthwhile information out of them.

The way I push myself in front of the stupid bus is by intentionally putting myself into situations where I cannot possibly provide a 100% smooth delivery. For example, instead of spending an hour to refresh myself on a complex code question before hopping on a 1:1 screenshare (presumably so I can look like a total smartass), I will ask the other teammember to fire up a screenshare right away without any planning. The consequence is that I inevitably look a little lost every time and the other team member has to remind me of the gaps as we go through the problem.

Over time, I believe this builds a strong sense that even the lead/architect is not better than anyone else and that we all have an ongoing role in keeping each other synchronized on the relevant domain knowledge.

This ties closely to plausible deniability. I seriously think this field is under developed and more people need to learn from an early age how the most plausible sounding explanation is not always, and maybe in certain fields even often, not the right answer. It's easy for engineers to intuitively grasp this since we see so many oddball failure modes in software development.