Genly Ai is an emissary for the Ekumen on Winter, hopeful to open Winter to trade between worlds. However, Ai has a difficulty navigating a society and a world where people are ambisexual, and don't fit into particular gender roles.

Ai makes disparaging remarks throughout the novel about the residents of Winter, associating negative values to what he ascribes to female or womanly, while praising masculine values. His misogyny runs through the entire novel, insidious, hidden to all but him.

I suspect Le Guin's intent is to hold a mirror to ourselves, and let us see how we react (or don't!) to our behaviors reflected through Ai's actions.

I don't know that Ai fully recognizes his failures or weaknesses. I suspect we're intended to see and grow from them, not Ai.