Probably not what one was referencing but..
some forms of Buddhism state that outward appearences of things do indeed contain the same character as our interior minds or things perceived as interior. However the interior, our perceived mind is closest to us and then easiest by far to use to attain insight into things to include exterior. One first starts interior then it displays as outer as well. To start with study of perceived exterior is considered very difficult.
So..."Does an inward outlook lead to outward insight?"....outlook may infers a set standard of measurement, so in that context no, not necessarily... as insight is a more fathomed thing. Outlook however could be a general term to describe perhaps a means as in....I watch mind, that may be a outlook. I have the outlook of always studying things, that may be a outlook in this context. Producing a outward insight, or a insight into the significance and perspective of outside objects by use of a means which may be considered to be a outlook....yes, that may be so.
"This order considers that progress can be achieved more rapidly during a single month of self-transformation through terrifying conditions in rough terrain and in "the abode of harmful forces" than through meditating for a period of three years in towns and monasteries"....Takpo Tashi Namgyal.