For someone as successful as Trump? The answer is both. He does plan it out, but leaves it open just enough to react to unexpected things. He reacts fast to unexpected things because of the business and real estate company he made. He would have stayed in bankruptcy if he wasn't. On top of that he has very good people that know what they are doing, and work as a team as well. Gets rid of the ones that hamper, and helps those that he has to let go for an external reason instead of internal.

Then the most important part(to me at least) He has a large swath of this nation, and people around the planet praying to God to help guide him as well as to reveal the darkness that covers the enemies.