Prizes are awarded each spring in the categories of fiction, nonfiction, poetry, and drama.
Nominators are chosen for their expertise in the literary field. They may be writers, academics, critics, librarians, booksellers, editors, theater producers, directors, former prizewinners, and others whose recognized expertise serves to produce a range of nominees that represents the breadth, depth, and excellence of literary production in the English-speaking world. Nominators make two nominations. They submit a letter of recommendation for each nominee, as well as the titles of one or two exemplary works. The prize office creates a dossier that includes the nomination letter, written works, selected reviews, a brief biography, and a list of publications or stage productions.
The President of Yale annually appoints a three-person jury in each category that consists of a mix of jurors from within Yale and outside the University. Juries convene in November to select a list of four finalists in each category, and compose support statements for each. The list of finalists is submitted to the prize selection committee, which makes the final decision on winners in all four categories.
The prize selection committee consists of nine individuals. Donald Windham named two lifetime members in his will. The President of Yale appoints the other seven. These include two Yale professors and five committee members from outside the University, including the committee chair. Members meet at Yale in the spring and formally announce their selections after giving winners the news.
Although winners are announced in the spring, they do not receive their awards until September. All prizewinners must receive their awards in person and participate in a multi-day literary festival showcasing their work and celebrating their accomplishments.