How the Digital Era Has Changed the Daily Crossword

A: Some crossword grids are easier to flesh out than others, but they tend to follow a similar design approach: brainstorming a “theme set” around an interesting idea for wordplay, building the puzzle grid’s skeleton around this set and filling it with all the answers through trial and error.

Once the grid is complete, the final step is writing clues for every answer, keeping clarity, variety and the right difficulty in mind. The most important aspect of this process is remembering the solver throughout; the puzzle should not just check the boxes for its creator, but be enjoyable for its target audience.

The puzzle design program I use is a Mac-only application, CrossFire, which allows me to lay out, tweak and save my puzzle grids with ease. I personally view the tool as an alternative to the tedious sketching, shading and erasing on graph paper — how I first explored puzzle making — though it does feature many bells and whistles that other crossword creators find helpful, such as “autofilling.”

Many of my peers curate master word lists that contain hundreds of thousands of crossword-worthy answers scored by a perceived enjoyment factor. A fresh, lively phrase might receive a 75; a familiar, normal word, 50; a bit of esoteric trivia, 30. Puzzle makers are constantly adding to their own word lists, which can be imported into CrossFire and used for quick, computer-assisted filling of an optimal solution based on a set scoring threshold. While autofilling certainly doesn’t guarantee that a solution is possible, the technique eliminates concerns of human oversight, and is especially useful with a well-maintained word list.

As my methods for finding answers are done manually, I rely on querying strings of known and unknown letters using puzzle and word databases like XWord Info and OneLook.

For instance, if I type the pattern N??B? into a database, the query will return possibilities like NUMBS, NOOBS, NUBBY, NIOBE, the partial phrase NOT BY (as in “___ a long shot!”), and various obscure proper nouns and abbreviations. It’s up to me to determine which option is optimal, as both an answer itself and as a constraint on the rest of the puzzle grid. Although this approach is quite time consuming, I find it strengthens my abilities to recognize patterns in words, and I’m up for the challenge.

A: The puzzles I create are all done on my own time. My daily routine involves working with the puzzles editor, Will Shortz, and the digital puzzles editor, Joel Fagliano, with the three of us making up The New York Times Crossword’s editorial team.

All crossword puzzles published in The Times have been accepted through our open submission process. The backbone of my job consists of reviewing puzzle manuscripts that are sent our way, and then corresponding with the puzzle makers to inform them of our decision, as well as offer constructive feedback where appropriate.

Each puzzle is judged holistically, under the same considerations discussed with crossword creation: the interest of the theme, the quality of the surrounding grid and answers, the appropriateness of the clues. If we like a puzzle, we accept it and file it into our queue; its clues will be edited for style and accuracy in the weeks before publication.

At the forefront of this entire process is a need for information, which is now quickly and readily available in the internet era. Sometimes I’ll need to verify an answer unfamiliar to me; Will’s bookshelves are lined with trusted reference works, but a simple web search on a term can be done with the click of a button, and it can sometimes lead me down a rabbit hole that ultimately inspires an interesting clue.

A: There is certainly something to be said for solving a newspaper crossword in pencil, just as there is for holding a physical book to read.

However, solving online offers a truly enhanced experience. Crossword neophytes may find digital-only features like Check and Reveal to be especially helpful for moving through a puzzle more quickly, perhaps learning a new word or two with minimal frustration. The built-in timer serves not only as a barometer of puzzle progress, but as a data collection device for showing solvers how a time compares with their average on a given day of the week. All can appreciate the beauty of immediately seeing the clue that corresponds to selected squares in the grid, as opposed to searching through the columns of clues in print.

A digital platform for solving also comes with a digital archive of all past puzzles, as well as other daily offerings, like Joel’s Mini Crossword and our latest word game, Spelling Bee, which I edit. A print solver is generally finished for the day once the corresponding puzzle page has been completed, but an online solver has the ability to start, stop and continue many puzzles at leisure. Progress is always saved in an account, and a login allows access on any electronic device.

On the editorial end, the cohort of online solvers adds a new ripple to our review process when we consider how a puzzle should be presented. This has always been simple in print; the solution grid is displayed in the next day’s paper, and solvers can check their work manually. However, with online solvers entering their answers against a solution key in our back end, things can get complicated, especially with tricky theme ideas that can be interpreted in various ways. We have published puzzles in the past with squares that contain multiple letters, different correct letters for Across and Down, or no letters at all.

A: I’m a big sports nut, and have gotten super into the app Clutchpoints for keeping up to date with pro scores and analysis. The elegant, easy-to-use interface is its selling point, and game updates display better in real time than they do in any official apps l’ve tried in the past. Clutchpoints isn’t just for one sport, either; the user can toggle between Major League Baseball, the NBA and the NFL with ease.

My favorite part of the app are the game feeds themselves. Next to each box score is a Stream tab that integrates the live play descriptions with social media updates from professional fan pages and well-known analysts. The game might already be on my TV, but now I can have its details peppered with Twitter GIFs and hot takes in the palm of my hand.