The answers to the May 29th New York Times crossword puzzle included “epicness,” “twitter hashtag,” “where it’s at,” and “hell no.” Although the 61-year-old Will Shortz edits every single submission that graces the Gray Lady’s pages, that day’s entry (a Thursday) had sprung from the mind of 23-year-old Anna Shechtman, Shortz’s assistant and a four-time puzzle contributor for the Times.

Anna Shechtman

Since starting at the Times straight out of Swarthmore college last year, Shechtman has brought some youthful edge to the 72-year-old quadrant of the paper. Not only did Shechtman get Shortz to include clues like “State of being awesome, in modern slang” (answer: epicness) in her own puzzle, she has influenced dozens of other grids, helping to justify more modern words and clues.

In addition to the standard assistant duties, like helping out with mail and sending rejection letters, the bulk of Shechtman’s day is spent cluing. Once a puzzle and its theme is accepted, out of the hundreds of entries each week, the two work in Shortz’s Pleasantville house to bring the grid up to the Times’ standards, she explained. “He’s a very hands-on editor, so he will actually make changes to the grid to make the words more worthy of a puzzle,” Shechtman told Fast Company. “From there, we’ll go on and change probably about 50% to 80% of the clues a constructor has written.”

A constructor’s dream is to have a solver have a delayed or belated ‘aha’ moment.

The main goal is to get rid of crossword-puzzle-eze, words like “aria” and “ulna” that constructors use as crutches because of their letter combinations. (Vowels and consonant-on-consonant phrases prove extremely useful in grid construction.) Shechtman and Shortz weed out as many of the common words as possible, swapping them for more interesting words and phrases. The process often includes free association, the consultation of multiple dictionaries, including slang and niche dictionaries, and Internet rabbit holes–all in the name of finding a clever way to hint at a word or phrase.

The best puzzles make people smile. “A constructor’s dream is to have a solver have a delayed or belated ‘aha’ moment, something like an ‘Oh!'” Shechtman explained. For anyone who has figured out the gimmick to a crossword, you know the feeling she is talking about–that moment when you get the hidden theme or joke.

New York Times Crossword, May 29, 2014 Copyright ©2014 “The New York Times Company.” Reprinted by Permission.

For her recent Times puzzle, for instance, Shechtman used the theme “sharp.” The clues “#1,” “#2,” “#3,” and “#4,” all had answers whose shapes–much like the accidental used in musical notation to indicate a sharp note–are also pound signs, like the Twitter hashtag or a tic-tac-toe grid. “Just had the biggest ‘Ohhhhhhhh…’ moment I’ve had in a long time,” puzzle reviewer Rex Parker wrote that day on his blog, where he solves the Times crossword and reviews it every single day. “Aha” moments can also happen on a clue-by-clue basis. “Bubblewrap” for “It might pop in the post office,” for example.

In helping Shortz create more “aha” and “oh” moments, Shechtman has brought both a youthful and female perspective to the puzzle. By watching the trailer for Bad Neighbors and YouTube clips of How I Met Your Mother, Shechtman recently got Shortz to change the way he clued “bro.” He usually goes with something like “sister’s sib.” “I think the word has come to mean a lot more. It’s loaded with a lot more cultural significance than that,” she said. In a February puzzle, the clue read: “Preppy, party-loving, egotistical male, in modern lingo.”