Creating Corporate Trivia Contests Where 100% of the Questions are Client-Specific

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Recently, I was challenged to do something I’m not often asked to do: produce a trivia team building event in New York City where 100% of the questions are client-specific.

Now, I know what you’re wondering: “Hey, wait a minute, David – aren’t ALL TrivWorks events customized for each client? Isn’t that what you’re all about? It says it all over your Website, after all!” The answer to this is yes, ALL of our events are customized for each specific client, event and audience – to a degree.

I offer minimally-customized events, where I send the client a questionnaire in advance to get a basic understanding of the attendees, goals, and purpose of the competition. I then draw appropriate questions from my database – pop culture and general knowledge questions, which I know will go over well based on over ten years of experience producing events for similar clients from related industries, with the same type of participants.

I also offer what I dub a fully-customized event, which involves a comprehensive customization call in advance of the gig, followed by researching and writing original content specific to the event: questions about the company, key messages, even individuals present. However, these events are also rounded out with appropriate general knowledge and pop culture trivia, again based on my unique specialized experience and expertise producing trivia game shows for corporate events.

However, every now and then – I’m talking just a handful of times a year, really – a client comes around who wants ALL of the questions to be about them. No world history or geography, no TV or movies – forget “name that tune” or celebrity photo ID. They want every question to be about them.

Every. Single. One.

Depending upon the duration of the event they are seeking and how many rounds of trivia they want, this could work out to 50 questions or more. Let me tell you, that’s a lot.


To help elucidate you on just how much work goes into producing highly-customized gigs such as this, I thought I’d take you along on a virtual journey from beginning to end. Here we go!

The Challenge

First, let me ask you do something: come up with a trivia question about your company. Not just any question, mind you; it has to be not too easy, but not too hard. It also has to be something any of your colleagues can answer, not just the “old guard.” Oh, and it has to be fun.

Not so easy right? Now, do that 50 times.

Get the idea?

The typical customized event I do is made up of 3-5 full-room trivia rounds, ten questions per round, each of a specific theme. The questions are expertly tailored to be appropriate for the exact audience in attendance: age range, gender ratio, nationality, and about a dozen other key demographic traits (follow this link for another article I wrote on how we customize the trivia at our events). Questions custom-written specifically for the client are then typically sprinkled throughout the rounds; at the client’s option, we may also lead off with a dedicated company-specific round of ten questions.

We want the competition to feel personalized, but it’s not intended to be a quiz of how well attendees know their company and/or colleagues. In my experience, the above formula provides a perfect balance for just about any company entertainment event or occasion.

However, when a client has a specific type of event in mind – one where EVERYTHING is specific to them – I have to accommodate accordingly. It isn’t easy, even for someone like me who’s been doing this forever and is quite good at it. But deliver I must, so…bring it on!

Gathering the Data

One thing I’m really, really big on is minimizing the amount of time the client has to spend on the customization aspects of our events. Planners want this to be easy, not hard; folks who have never worked with me before are thus understandably nervous when they see the word “customized,” because they fear that means hours out of their day having to compile and write trivia questions about the company.

First off, I do NOT want clients writing actual trivia questions – even for highly-tailored events such as the ones we’re discussing here. Doing so it not only time-consuming for the client, but in all honesty is a pain in the rear for me. Why? Because whereas I craft trivia questions professionally for a living and have been doing it for over twelve years, most people have not. They don’t know that there is an art to writing great trivia questions, particularly those which are intended for a specific audience and purpose.

What I instead ask is that they provide me with raw data points: facts, figures, stats, key messages, etc. which I can then convert into actual trivia questions on my end. Not only is this smoother and simpler for the client (which I always strive to do), but it gives me plenty of material to work with from a creative standpoint. I’m extremely adapt at taking even the most dry, boring data, and turning it into fun, humorous and compelling trivia, which anyone in the room can have a shot at answering correctly.

Choosing the Categories

Because I won’t have the usual broad-themed categories I usually work with (“General Knowledge,” “Current Events,” “Movies & TV,” etc.) I need to instead find another way to thematically focus the questions I’m crafting. Two things are important here: the material I’ve been provided with, and the client’s priorities.

What I’ll do first is review the entire trove of stuff I’ve been given by the client, and start mentally dropping the questions into buckets. Most often, these break down into:

  • History
  • Products/services
  • Capabilities
  • People
  • Culture

Next, I’ll turn to the client and say: what’s most important to you? Do you want the focus to be on reinforcing certain messages surrounding core values? Or perhaps you want people to learn about each other? Also, is there anything the client does NOT want to dwell too much on? (When I was prepping an event once, a client sent me a PowerPoint deck as the source material, about half of which was densely packed with information about their individual products. When I returned the trivia questions we’d drafted based on the material provided, she said “This is nice, but I didn’t want any the products included – that’s not the priority of this event.” Lesson learned.)

Drafting the Questions

As mentioned above, I’ve developed a strong acumen over the years for writing solid trivia questions for live events. When I don’t have any general knowledge or pop culture at my disposal to mix things up, the new challenge becomes: how do I keep this interesting?

I like to mix things up with a variety of trivia formats and styles. For each round, I’ll include some straight questions (“In which year was Company X founded?”), some “dovetail”-type questions (“Company X was founded in 2006 – the same year Martin Scorsese won his first Academy Award for which film?”), and a select number of multiple choice questions (“Which of the following is NOT a product or service we have ever offered?”). This helps ensure the event is fun and fresh, even if the content is focused exclusively on the company.

Sequencing the questions is another important aspect: which questions come at which part of the round, and which categories come at which part of the event? This again is based on both art and science, which I’ve written about previously.

Building the Slide Deck

Oftentimes, a highly customized corporate game show is accompanied by a PowerPoint deck which has been built exclusively for the event. For this, I need not only the logo (either that of the company, or of the event if a dedicated logo has been crafted), but the color scheme, hashtag (if applicable), and any images provided by the client.

I don’t like putting up the actual trivia questions on the screen, and especially not EVERY question. To me, this is a distraction for the audience, and forces people to stare at the slideshow rather than to each other while they collaborate – which for TrivWorks events is the entire point. The two exceptions here are A) if a client specifically requests this for some reason or another (and despite my recommendation otherwise), or B) if there is an international audience where a significant number (or all) of the audience speaks English as a second language. In these cases, we HAVE to put all of the trivia questions on the screen, to help make sure that those participating can actually comprehend the queries.

When client-specific images are being used in the slide deck, I’ll selectively have some images accompany the questions, while some accompany the answers as a “reveal.” This again helps keep things fun and interesting, and adds an element of both the unknown and a “surprise” for what might appear – and when.

Review & Approval

If a client is having us prepare such a highly-tailored, company-specific event, it is often because the audience is extremely important: valued loyal clients, senior executives, partners, or what have you, and we need to make the experience memorable. As such, I can almost certainly guarantee that they will want to review and approve everything prior to the show.

For me, this can actually be one of the most challenging and time-consuming parts of the process. As I’ve said, I know what I’m doing: I’ve completed an exhaustive review of the data I’ve been supplied with, conducted additional supplemental research, painstakingly crafted and fact-checked the questions, and built a corresponding PowerPoint deck. To get the material to the point where is it client-ready, and then send over for their review, is therefore a bit of a nail-biter.

Under the best-case scenario, the client will love what we’ve produced for them, and sign off. Other times they may have a few change requests here and there, before giving the green light. Unfortunately, however, there are times when they want changes – BIG changes.

Producing what may turn out to be just the first draft is a labor of love for me – I won’t send anything to a client for approval unless I know in my gut that it’s 100% ready, that it will go over well and be an absolute hit. I therefore admit it’s frustrating on my end when a client then turns around and slashes the whole thing to ribbons, after so much time and effort has already been expended.

But I am in the service industry – it’s my job to deliver to meet my clients’ expectations, and to deliver what I said I would. It ultimately doesn’t matter what I want (even if I know what I’m doing, and that my original product will be well-received); rather, it’s what the CLIENT wants. At this point, it’s time to put my ego in check, swallow my pride, and give them what they are seeking. I’ll do whatever is needed, as many rounds of revisions as requested, until I get that “Approved” Email.


Events where 100% of the material is client-specific isn’t something that happens often. It requires a lot of effort on my end, far more than I would typically need to devote to an individual gig, and in my opinion really isn’t necessary to deliver a fun & engaging group bonding experience. And while every client I’ve ever produced a hyper-customized event for as been extremely pleased with the result, there’s no way to say for sure whether the audience would have been just as happy (if not more so) with a healthy mix of appropriate non-custom questions as well.

But ultimately, all that really matters is that the attendees have a blast, the goals of the event are met, and the planner looks like a hero for bringing us in. It can definitely be rewarding working so very hard on individual events such as these, and to see them be well-received by the audience. Attendees appreciate the obvious effort to tailor the experience in such a detailed fashion, and there’s no question that the program is made-to-order, rather than a one-size-fits-all turnkey solution. While I’d rather not do TOO many events like this, I’m cool with it every now and then.

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