DER: My word list originally started as a few English dictionaries combined with words that had previously appeared in crossword puzzles. Since then, I’ve probably added many thousands of words by hand. I try to pay attention to interesting words and phrases that come up in everyday life and I’ll add those to a list on my phone using the Notes app. I’ll check that list first when I’m filling a grid, whether that’s a themed puzzle or a themeless.

PASCO: I have a basic word list, which I haven’t maintained a lot. The only real changes I make are when I add new, fresh words that I want to include in a crossword. I can go into the program and manually give those words high scores in my list, so they get priority when I’m filling grids. I also fill manually — I use Crossfire, but I don’t use the Autofill feature. It takes longer, but guiding the whole fill process by hand makes me feel more in touch with the crossword. It really helps me get a sense of what letter patterns work in a grid and which ones don’t.

DER: If you rely on Autofill, that guarantees you won’t have the opportunity to introduce something new that isn’t in your word list, so we discourage it. I prefer a semi-supervised approach — using software to verify the fill you have so far still works, and suggesting words that you might want to put into the grid next, while you select words by hand. During that process, I often think of words that would also work, but weren’t in my list.

PASCO: One good resource for finding words outside your word list is Onelook.com. If you have an answer like ??RK??A?, you can look it up on the site and get a list of words that match that pattern. This has bailed me out so many times when filling a grid — sometimes, all it takes is one entry you hadn’t thought of to hold together an entire section.

Quality Is Never an Accident

PASCO: In terms of the words themselves, my fill philosophy is “clean fill above everything else.” Filling by hand guarantees that every part of the grid gets my attention, so junk words are less likely to slip in.

DER: I’ll second that. How you fill the grid doesn’t matter as much as ensuring that every word in your grid is high quality. Ideally, it should seem like you purposely chose every word to be in your crossword. This is especially true for themeless puzzles, where you begin with no constraints. Most constructors try to inject fresh words and phrases, often from current events or pop culture, that have never appeared before in a crossword. Other than that, we strive for liveliness, which is ultimately a judgment that can vary among constructors and editors. Conversational phrases like “WAIT, WHAT?” or “DON’T ASK” are always fun to include in a crossword. It’s hard to describe objectively, but most constructors would agree that ESCAPE ROOM and SUBTWEET (which Paolo debuted) are more lively than, say, the unremarkable ESSENCES or, ALAN-A-DALE, which is dreaded for its overuse.

PASCO: Thanks for the shout out, Kevin! By “debuted,” we mean that it appeared in The New York Times Crossword for the first time. Constructors like debuting words, since it usually means that they’re fresh or new.