The Art & Science of Writing TrivWorks-Style Trivia Questions

New.York.City.Trivia.Host.jpgNew York City Trivia Host

This is a topic I don’t write about often on my blog. I know I own a company specializing in trivia team building, NYC and Southern California and everywhere in between. However, as I’ve also discussed here on these cyber-pages, remembering and recalling random facts isn’t really my “thing.”

I come from the events world; what’s always excited me was creating positive experiences for others to enjoy, particularly group bonding events – be it scavenger hunts, quiz nights, parties, or other fun goings-on. I kind of fell into this line of work ten years ago (almost exactly, actually – next month will mark a solid decade as a professional quizmaster, if you can believe it), and while the format and material lends itself to my personality, being a “guru” isn’t what drives me. This is especially true considering, paradoxically, I’m pretty lousy at trivia.

But this is my thing now, and as such, I’ve got to write new questions – like, all the time.

Somebody I recently met asked me what my process is for writing questions. It’s funny, I’ve been doing this for so long that I actually never think about the procedure, I just go into autopilot and do it. But I’ll share that method with you anyway.

First, a little bit of background. When I started doing this as a Manhattan pub quiz night host, I was like, “Great! I know a bunch of fun trivia questions!” I imagine you know a few as well. The problem is, of course, that with quiz night, you need to come up with fresh and original material each and every week, to build a following. In my case, that was 50 questions PER WEEK. So come week 4 or 5, I suddenly found myself staring at a blank Microsoft Word document, the cursor blinking tauntingly at me on the screen, and having absolutely no idea what do to.

I’ve since retired from hosting bar gigs (at my peak, I was hosting two different Manhattan bars per week, and Brooklyn every other week – so eight to ten per month), but when you’re forced to come up with that much content, I found a few tricks which helped. First, my radar was always up. Whenever I saw something, heard something, or even had a random fleeting memory about something, I’d write it down on my phone notepad ( a flip-phone, mind you). When I’d pull that phone out and re-visit it later while writing, I’d then be able to remember it.

I also kept an eye on what I felt people responded to best. Did they like pop culture? History? Geography? Literature? Also, what did they hate? This helped me select the right material, but it was still a challenge always coming up with broad, random tidbits of information to use – knowing it had to be not only relevant and interesting, but also not too easy, and not too obscure.

When I started producing Pat Kiernan’s trivia nights at The Bell House in 2011, that’s when my style of writing really changed. For those of you who have never attended, the way our collaborative events work is we have four full-room rounds, four “mini game” bouts of 1-on-1 games, and a “showdown” grand finale made up of 15-30 questions. What made drafting the material at these events different from pub quiz was that for the bars, it could be much more random; with Pat’s events, we have focused themes. Over the past five years, these have included pop culture, New York City, 90s, 2000s, food, summer, winter, books, awards and more.

Each full-room round and mini-game needed it’s own sub-category of the overall theme; therefore, with a 90s trivia event, we needed a round “90s TV Shows,” “90s Movies,” “90s Celebrity Scandals,” etc. As the writer, this meant I had to be far more focused in which questions I was writing. I found that this focus really helped me; whereas before I was grasping at almost anything I could see, hear or remember, I was now centering in on very specific areas. It was extremely useful to challenge myself in this manner, to try and come up with fun and interesting questions which were appropriate to the theme each time.

Also helping me to up my trivia writing game was Pat Kiernan’s personal review and counsel. He always offers me feedback on the material, be it for public gigs at The Bell House or our corporate events. As a veteran game show host (he emceed VH1’s The World Series of Pop Culture, among others), as well as a broadcast newsman, Pat is highly attentive to detail, and is really a natural at distilling questions. Whenever I submit what I’ve come up with for him to review, he always sends me thoughtful, detailed notes: “This question’s a bit vague,” “we need to cite a source here,” “too obvious,” “too hard,” “let’s reword this,” etc. This kind of guidance has undoubtedly made me better at what I do, and raised my standards considerably when drafting new work.

Of all the different aspects of my unique line of work, writing the queries isn’t my favorite part. It’s extremely time-consuming, at times frustrating, and can be a considerable drain on my energy. However, once I sit down and actually start immersing myself, I admit I do get into it. I thrive on the challenge of coming up with fun, sharp-witted questions which I think my intended audience will enjoy, and that hopefully will elicit laughs as well. Even when I’m preparing events that Pat’s not hosting, I still feel like I’m wearing a “Pat Lens,” constantly asking myself, “is this clear enough?” “Can I verify this?” “Will this be too easy, or too difficult?” I feel very fortunate to have had Pat’s tutelage here, and that his discerning eye and high standards have really upped the quality of what I produce.

I’d be very interested to hear from others who craft quiz questions regularly, to learn of your process for generating fun, clever and original material. Please leave your thoughts in the “Comments” section below, or hit me up on social media!

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