Trivia Questions For: Will Shortz, New York Times Crossword Puzzle Editor

It’s time for another edition of our “Trivia Questions For…” blog interview series, where I have the pleasure of speaking with leading experts on topics important to TrivWorks’ audience. While focusing mainly on team issues such as morale, communication and improving the modern workplace, it’s also important to explore the creative side of brainy activities like our trivia team building events – as such, I am so incredibly honored and excited to have caught up with Will Shortz to talk shop!

One of the most familiar faces the gaming world, the name Will Shortz is synonymous with puzzles. After earning a self-designed degree in “enigmatology” – the study of puzzles – Will went on to start one of the most inspiring careers ever, in which he truly followed his passion for creating puzzles and games. He has been the crossword puzzle editor for The New York Times since 1993, and has been the puzzle master on NPR’s “Weekend Edition Sunday” since the program was started in 1987. The author or editor of over 500 books, Will is the founder/director of the American Crossword Puzzle Tournament, which was the subject of the 2006 documentary Wordplay.

Needless to say, Will holds a truly unique perspective on how to design challenging games and enjoyable experiences for others – as such, today I am asking him about why people are so passionate about games/puzzles, and his approach to designing them.

1.         As a crossword puzzle constructor/editor, you have made a career out of creating experiences for others to enjoy. What do you find most rewarding about your unique job?

Several things: First, I learn new stuff every day. That’s always fulfilling. Also, I enjoy the creative process of writing crossword clues with original puns (like “Chain stores?” for JEWELERS) or surprising trivia (“Home to North America’s only year-round ski resort” for MT HOOD). But most of all I enjoy the people I come into contact through puzzles. They tend to be smart, interesting, well-read, playful, and often funny. It’s a good group to be around.

2.         As we saw in “Wordplay,” people are passionately competitive about “mind games” such as crossword puzzles, trivia, etc. Why do you think that is?

We all like to test ourselves and see how we rate. For an activity like crosswords, which are usually solved alone, a crossword tournament (as shown in “Wordplay”) is a rare way to see how we stack up against others — as well as to meet other people with a common interest and a similar sensibility.

3.              Who are the best people to create games for? Who are the most challenging?

I’m fortunate to work for two news organizations — “The New York Times” and National Public Radio — with smart, elite audiences. So the puzzles I make and edit for them can be more sophisticated than they can be almost anywhere else.

 4.              In an increasingly technological world, do you think “low tech” games requiring a pencil & paper have a future? Why or why not?

Crosswords are doing fine in the electronic age, as more and more people are solving them online. Still, I think something will be lost when print newspapers disappear, as I think crosswords are ideally suited to the print medium. There is a tactile pleasure involved in writing letters on paper. It’s not the same typing on a keyboard.

 5.              Now, a selfish question: If you could give one piece of advice to those who create puzzles/games professionally, what would it be?

Test your puzzles/games on as many people as possible and listen to their responses. Adapt your work as necessary.

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Now, Will has a trivia question he would like to ask YOU, and it’s one of his favorites:

It’s a trivia question that my friend Henry Hook wrote years ago: Why was it necessary for Admiral Byrd to take along a refrigerator on his Antarctic expedition? 

Write your answer in the “Leave a Reply” box below. You can also connect with Will via his Website www.WillShortz.com, as well as via Twitter @Will_Shortz.

Do you have questions, comments or thoughts regarding this interview? Please feel free to share below as well!

(Photo courtesy of Donald Christensen)