Trust-building exercise: Impossible Questions

I was recently reading the following from an old article on Joel on Software about interviewing software engineers, when I came to his typical interviewing process:


Introduction
Question about recent project candidate worked on
Impossible Question
C Function
Are you satisfied?
Design Question
The Challenge
Do you have any questions?


I noted the 'Impossible Question' nested there in the middle and immediately thought that perhaps he was giving an example of a bad interviewing process. But no, it was his own method (...at the time. He now has an updated post on interviewing: GuerrillaInterviewing3)

Here is his description of the way he (at that time) approached the 'Impossible Question':


*****
OK, the third thing on that list is the impossible question. This is fun. The idea is to ask a question that they have no possible way of answering, just to see how they handle it. "How many optometrists are there in Seattle?" "How many tons does the Washington Monument weigh?" "How many gas stations are in Los Angeles?" "How many piano tuners are there in New York?"

Smart candidates will realize that you are not quizzing them on their knowledge, and they will enthusiastically leap into trying to figure out some back-of-the-envelope answer.
*****


I stopped after reading this to analyze the mingling feelings of dread, numbness, and envy that I was feeling, surprised since this was an informative article by a knowledgeable person. Why should I be anything other than interested and happy to learn from it?

I realized that I felt a bit put-off by the section: "Smart candidates will realize that you are not quizzing them on their knowledge, and they will enthusiastically leap..."

I feel that I am a smart person, but would not have responded to the Impossible Question that way at all. I think that perhaps a better adjective than 'Smart' would be 'Confident', 'Experienced-with-interviews', or even better:'Trusting' ... because my first emotional response upon imagining being asked the examples of 'Impossible Questions' was not a leap into an enthusiastic challenge (that contained too much variability to have any hope of being accurate in), but to think to myself, You don't really want to hire me, do you?

It occurred to me that my past ... 5? 8? Years of significant human interaction since leaving home has carried strong elements of feeling that if I am not careful, people will set me up, take advantage of my goodwill or whatever else they want from me for their own sake, and discard me for not fulfilling impossible (usually unspoken) demands if they have the chance. At least being asked an 'Impossible Question' gives me a chance to realize what game is being played and exit by accepting the better situation of being discarded sooner than later. If I really want something out of a situation, and can play the game long enough, then it can work. If there's not something I want so much, then Ok, we both know what's going on. I'll be going now.

It occurs to me that in good situations, this sets me up to feel always on edge, always needing to cross my t's and dot my i's and use exactly correct punctuation. It has kept the monsters from leaping out of the shadows and devouring me so far, so I keep doing it. Even when it doesn't work, I keep doing it because it seems like the best way to keep the monsters down. Every now and then, I don't see everything through to the last iota, partly because I may want to assert the ability to assess that it's not always worth it, and perhaps also to give someone a chance to discard me for not being perfect, although, in a situation where I don't have to feel like I should have been expected to be perfect.

This kind of response may be preventing me from reaching for speculative challenges. How many piano tuners are there in Seattle? I think it would be completely absurd to try to actually estimate that with any kind of confidence. However, thinking about it might be interesting in that the attempt to come up with the most reasonably possible estimate might produce some interesting thoughts or connections as side-effects. It can be fun to wonder about something together as long as no one is tricked into thinking they are actually right.

It was good of this article to show me this conflict in ways that I am vs. ways that I can be, and would like to be. I've been needing things like this.