He was deliberate in counsel and prompt in action, which may have seemed indecisive to his father Josui; it is said Josui warned Nagamasa by telling him something like, "I have been told by Takakage KOBAYAKAWA to be cautious, because I make decisions too quickly, but you need to be careful because you are the opposite."
熟慮断行の気性であったようであり、父如水はそれを優柔不断のように見えたのか長政に「自分はかつて小早川隆景に物事の決断が早すぎるので慎重にしたほうがよいと言われたが、おまえはその逆だから注意しろ」との意味の言葉をかけたらしい。