Collin Waldoch of Water Cooler Trivia: “Positive Team Culture”

Positive Team Culture: If you want to improve employee relations, you need to create an environment where team members feel safe to fail and learn. Quite simply, this is something I try to live every day at Water Cooler Trivia. We are building software for trivia quizzes, it’s supposed to be fun. Staying upbeat and […]

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Positive Team Culture: If you want to improve employee relations, you need to create an environment where team members feel safe to fail and learn. Quite simply, this is something I try to live every day at Water Cooler Trivia. We are building software for trivia quizzes, it’s supposed to be fun. Staying upbeat and positive trickles into the product we are building for thousands of companies around the world.

As a part of my series about about how leaders can create a “Fantastic work culture”, I had the pleasure of interviewing Collin Waldoch.

Collin Waldoch grew up in the Chicagoland area where Jeopardy airs at 3:30pm each weekday, meaning it starts just after school lets out. Throughout high school, he would race home after the final bell rang to watch Jeopardy. More often than not, a few friends would tag along and a sibling or two would join (he’s one of six kids). They would competitively holler answers at the TV and keep their own scores along the famous trivia show. In short, he’s a lifelong trivia nut, so he’d always held out hope in the back of his mind that one day his career would revolve around the pride, the joy, and the relationships formed over trivial knowledge. Fast forward a decade, and the day has come! He is currently the co-founder/CEO of Water Cooler Trivia — they send customizable weekly trivia quizzes to work teams over email or Slack.

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I was bitten by the trivia bug very early on. In my opinion, quiz shows engage viewers at home in ways no TV show could, and for millions across the globe, they provide unparalleled family bonding time. Jeopardy was that quiz show for me. It was also a great way to bond with friends and family, particularly with my siblings. We did get quite competitive, but the moments spent shouting answers over each other are some of the most fun I have from childhood. It’s been my dream to actually be on Jeopardy — I made it to the final audition 3 times, and I will keep trying to go all the way.

The way my passion for trivia became an actual business that helps other businesses with their work culture begins with me bringing trivia to my first job. It was an internship at a major consultancy firm, and I got HR’s blessing to share a Google form with trivia questions with all of my colleagues. I wanted to inject a bit of fun but also create topics for conversation. To my surprise, dozens of responses came within minutes. Online trivia quickly became an office tradition there. I realized it would work anywhere.

One of the issues or barriers is that such activities usually require an in-house quiz master, but people come and go, or simply get tired of additional responsibilities. So, we decided to automate the process. It wasn’t difficult to find like-minded co-founders. I ended up recruiting my college pub trivia co-host and his software engineer roommate.

At the time we started Water Cooler Trivia, I was already a Product Manager at a large tech mobility company with experience incentivizing users and using gamification. So it all came together perfectly. Water Cooler Trivia started as a side hustle in 2018, and it really took off during lockdown, when companies began to value remote team building more than ever. This interest allowed me to leave my comfortable full-time job and focus on Water Cooler Trivia full-time.

Can you share the most interesting story that happened to you since you began leading your company?

One of the most interesting things we’ve done so far was take a break from working on programming and digital work to get our hands dirty with art. Although we knew very early we had a great product, we wanted to create a special experience also around its core.

We love that the winner is celebrated in the office each week, but we wanted to make this more fun with a quirky trophy that would rest on your desk until the next week’s winner came and claimed the trophy from you. So we took a pie-in-the-sky to design our own bobblehead trophies with cute little brains in them to mail to every company that signed up for Water Cooler Trivia.

We worked with a vendor in Asia to custom fabricate these trophies and passing the “reigning champion” trophy has become a beloved weekly ritual at many of our client companies. Of course, most trophies are currently gathering dust during the pandemic. For me, the entire experience of designing, manufacturing, testing, and distributing these trophies was a series of fascinating learnings because we are typically building software and writing trivia questions as our product. Hopefully we’ll be able to do more diverse, hands-on physical and artistic things like this after the pandemic.

Are you working on any exciting projects now? How do you think that will help people?

Our team has learned again and again this year that more of the workday is spent in team communication spaces such as Slack, Microsoft Teams, and Zoom. We know that these platforms can be overwhelming at times, so we’ve been working on introducing our “asynchronous” weekly fun with trivia quizzes one-by-one.

After tailoring our product for email and Slack, in December 2020 we are launching our Microsoft Teams integration for Water Cooler Trivia. We know that having a weekly message that builds camaraderie and gives teammates something to talk about that’s not the weather or weekend plans is a breath of fresh air during stressful times and newly-remote teams. We’ll continue to look for ways to harness the universal power of trivia to bring people together in a way that motivates them without exhausting them.

Ok, lets jump to the main part of our interview. According to this study cited in Forbes, more than half of the US workforce is unhappy. Why do you think that number is so high?

I think there’s an inherent tension between two trends that are increasingly common in the modern workplace. One trend is “bringing your whole self” to work and bringing down the barrier between how you act in your personal and professional life. The other trend is increasing levels of burnout across industries.

Frankly, bringing your “whole self” to work means that you are emotionally investing in more aspects of your life, and that creates the assumption that more hours is a good thing. Soon, you reach burnout. Burnout is made more common not just from more hours but more emotional investment in your workplace and relationships at work.

On top of that, most business leaders believe that remote work is here to stay. So far, it’s leading to people working more and burning out more. We need to find better ways to make it work for us.

The good news is that what we’re working on at Water Cooler Trivia is a way to get to know your coworkers and bring a sense of quirky, playful fun into the workplace without increasing your hours worked. But we are only a small part of the answer. In my opinion, there needs to be a fundamental change in how we talk about work and productivity. Happiness needs to play a more central role.

Based on your experience or research, how do you think an unhappy workforce will impact a) company productivity b) company profitability c) and employee health and wellbeing?

Although my own lived experience backs this up, the research and science says it all: unhappy workers make for unproductive workers. As the researcher Daniel Sgroi neatly summed it up in a 2015 study,

“In three different styles of experiment, randomly selected individuals are made happier either through the use of a short (10 minute) comedy clip or through the provision of drinks and snacks. We check that these methods make the subjects happier (they do) and then go on to show that these individuals have approximately 12% greater productivity than a control group.” –Daniel Sgroi. Source

Can you share 5 things that managers and executives should be doing to improve their company work culture? Can you give a personal story or example for each?


  1. Empathetic Leaders: Empathy means understanding the feelings and perspectives of those around you. It’s tremendously important for a team leader. The first time I truly felt “heard” by my supervisors as a 20-something in the workforce was when my supervisor related with me over how important family was in each of our lives.
  2. Consistent Communication: Keeping all team members informed about developments daily is going to help them to feel more organized and comfortable in their roles. Personally, the anxiety I felt in a new role at my prior job was 80% driven by inconsistent team communication patterns; once we settled into daily standups with biweekly project “check-ins,” it was
  3. Defined Objectives & Ambitions: Setting defined objectives and ambitions will motivate your team and give them a purpose. Put simply, people love goals, myself included. When I shared our goal for “1 customer-centric features per quarter” at Water Cooler Trivia it didn’t just help clarify our product roadmap, but also excited the team by being able to focus on features that made the product more fun without directly impacting our sales figures.
  4. Clear Roles & Assignments: Every team member should have a solid understanding of their exact role and how their efforts will help the team get closer to the defined objectives. This relates to consistent communication — in a past life, I was one of four product managers working with a group of 12 software engineers on a team. However, because we weren’t mapped to specific engineers, it was tricky to navigate imbalances with one product manager having more “engineering support” than others. Clearly defining teams or “pods” resolved this tension.
  5. Positive Team Culture: If you want to improve employee relations, you need to create an environment where team members feel safe to fail and learn. Quite simply, this is something I try to live every day at Water Cooler Trivia. We are building software for trivia quizzes, it’s supposed to be fun. Staying upbeat and positive trickles into the product we are building for thousands of companies around the world.

It’s very nice to suggest ideas, but it seems like we have to “change the culture regarding work culture”. What can we do as a society to make a broader change in the US workforce’s work culture?

That’s a big question, and one that should be the subject of wider debate and discussions. In that sense, as a society we should feel more open to talking about the workplace and workplace culture. We already see this in the media, but the conversation should be an open one at every level.

On an individual level the best thing we can do is assume good intent. Both in and out of the workplace, negative emotions that are expressed and harbored internally very frequently derive from assuming bad intent on the part of a stranger or coworker. The more we can assume good, earnest intent, the more we can productively solve disagreements and more forward an individual work project or broader relationship-building.

How would you describe your leadership or management style? Can you give us a few examples?

My leadership style is best described as “don’t treat others as if your time is more valuable than theirs.” The first example is actually where I learned this. In college, I worked part-time at a bagel shop where the owner would be the first one to grab a mop after a spill.

This initiative and willingness to put in elbow grease built credibility and trust amongst our entire team. Since that experience, I’ve continued to be willing to do the “small things” that others might consider “below” a CEO or co-founder, including a willingness, nay, eagerness to respond to individual customer emails, resolve issues, and write new trivia questions!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I started Water Cooler Trivia with two friends as a side project in late 2017 and did not make “the leap” to focusing on it full-time until winter 2020. That leap was only possible, practically and emotionally with the everlasting support and encouragement of my partner Alicia. She’s not just a supporter but also a regular brainstorm partner and an occasional trivia question-writer.

How have you used your success to bring goodness to the world?

The success of Water Cooler Trivia means that we can bring weekly trivia contests to more and more teams around the world! Most companies opt for a Monday morning quiz. This means there’s an email awaiting folks at the start of the workweek that they don’t dread — in fact it’s something they look forward to. Sharing this small joy with tens of thousands of folks weekly is the small, but meaningful positive impact we hope to continue spreading.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Make hay while the sun shines.” My grandmother says this all the time — she’s said it my entire life. The quote carries the same message as many other cliches — don’t delay what you can do now. It’s a one-liner that can energize through a tedious, difficulty, or draining task. It’s a one-liner that zings energy into my attitude. It’s something that makes me a doer, translating passive to active.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I know this is coming out of left field, but more biking and fewer cars on city streets. It opens up the local economy, humanizes the built environment, provides physical and mental well-being benefits, reduces pollution, helps us see and meet more strangers, the list goes on and on.

Thank you for these fantastic insights. We wish you continued success!

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