I've identified a flaw of mine: A desire to feel smarter than co-workers and the quick reading/degradation of people I meet. Are there any concepts/texts/philosophers(maybe psychologists) who discuss this in length?

I know people like that, and they tend to have never stepped out of the narrow path of top student, top uni graduate, top performer at job.

Try stepping out of that very narrow area of life. Once you see your many weaknesses outside of your narrow area of expertise, perhaps you won't be so quick to judge others in that superficial manner.

I run a fairly large company for instance, and it involves knowing something of everything, but many of the people who work for me would blow me away in their area. That's why I hired them. It would be strange for me to judge them as lacking, when they excel in their field and are therefore so valuable to my company. It would also be strange for them to judge me as lacking, when the risks I take are the reason their job exists.

That's a limited example, but hopefully you get the picture. If you just want a philosophy book to read, maybe try 'The Myth of Sisyphus' by Albert Camus. It might help cut down your ego (as it cuts down all of us to our base status as absurd creations).

/r/askphilosophy Thread