Ask HN: Your favorite resources to improve critical thinking, imagination?

Recently I worked with someone who was able to do design, think of corner cases, think of performance etc all in his head before he wrote a single line of code, for a complex piece of software. Most of the other people I've worked with people who write smaller pieces of code, test it out, refine it and repeat the process (including me).

This might sound strange, but my question is: Is it possible to develop this skill? What resources, exercises can you recommend for this purpose? He is able to analyze problems almost completely in his head/imagination, without using whiteboard or paper!