Reply #5: Not a good interview response, and I have a messy desk. [View All]

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The reason it is a poor answer is not that he has a messy desk (or a neat one), it is that he brought it up and characterized this trait as the "worst". His answer does give us a couple of clues about his personality, probably a lot more than he intended.

In the general population, people who are "clean" desk view "messy" as a failing, much like "morning" people view "night owls" and might fault them for sleeping later. (Here I am posting in the middle of the night and yes I have a messy desk.) Any "messy desk" executive has to have assistants to help
ensure that they are successful; while Obama said that he had good staff to compensate, his describing this as his worst fault suggests that he really doesn't have this under control.

Many of the most successful entrepreneurs and high tech executives are "messy desk" and thrive by creating environments that eliminates or delegates most of the bureaucratic functions, eliminates anything with low payoff, and frees them to leverage their talents to solve problems in new ways.

Seeing this as a fault also indicates some issues with self confidence, possibly that common trait of many very smart and successful people who still are afraid of somehow being found out as an imposter. Not enough info to really get into this at such a late hour.

At a minimum, every job applicant should expect this question and have a ready, if totally BS, answer. Otherwise, it shows they are unprepared and lack adequate care with information in a hostile environment.