Why imagining the worst can bring out the best in teams
Last month I ran a workshop with a college. The room was an eclectic mix: designers with impressive track records, department chairs, people from finance, technology, and marketing. I like that kind of mix—it forces conversations that don’t normally happen and when well orchestrated, it sparks new ways of thinking.
The first exercise was simple. Each group of four picked a card at random. The cards represented different industries I had sketched out in advance: a cruise ship, a hotel, a grocery store, a recording studio, an airline, etc. Their task: design the worstpossible customer experience, and then the best.
What always strikes me is how unnatural it feels at first. Our brains aren’t wired to imagine bad design. We’re taught to fix or improve. Yet the moment people start sketching out “the worst,” something shifts. They realize it’s not far-fetched at all. It’s often uncomfortably close to what we live every day.
I thought of my own experiences. The joyless hours stuck on a plane before takeoff, no water offered, no permission to get up. The endless snaking line at a hotel check-in desk while three clerks type slowly and avoid eye contact. Or walking into a grocery store where nobody—absolutely nobody—can tell you where the cereal aisle is. These “bad” designs are so familiar they barely need imagination.
The Worst Cruise Ever
And the scenarios people come up with can be hilarious. One group, tasked with imagining the world’s worst cruise ship, painted the picture vividly: you can’t actually book the trip without filling out three different paper forms, faxing them in, and then waiting for a confirmation call that never comes. Somehow, you still end up on the ship—only to find that nothing is included, not even water. The food? A buffet where everything tastes like it’s been boiled in the same pot: pasta, carrots, chicken, all swimming in the same beige sauce. Entertainment consists of a single TV in the lounge playing an endless loop of outdated safety videos. By the end of their presentation, the room was laughing and cringing at the same time, because we’ve all had glimpses of that kind of “bad design” in real life ( I experienced the VHS tape in an airline 10 years ago for real!).
And then, oddly, it becomes fun. People lean in. They exaggerate. They pile on details, almost competing for the most frustrating scenario. The energy rises. Laughter breaks through. And when they present their terrible experiences to the larger group, everyone nods in recognition. Because we’ve all been there.
That’s the magic of this exercise. By designing the bad, you lower the stakes for everyone—especially the non-designers. Finance, marketing, tech. They suddenly realize they don’t need formal training to spot what doesn’t work. In fact, their experiences are what make the exercise powerful. It levels the playing field.
Good design, after all, isn’t about making something look nice. It’s about making someone’s life easier, less frustrating, maybe even more delightful. And if that’s the goal, then everyone who’s lived through a bad experience has something useful to contribute. Which is everyone.
What happens in those sessions is more than creative brainstorming. Something deeper takes place: the barriers drop. People start listening to each other. They stop hiding behind their roles. For a few moments, the finance lead and the design chair are simply co-conspirators in imagining a better way.
And underneath it all, there’s empathy. Not the abstract, “design thinking” kind. The very real kind you feel when you remember what it’s like to sit on that grounded plane with no water, no answers, and no escape.
Bad design, by design, brings us back to that shared experience. It reminds us why design matters in the first place.
Tip: Next time you’re redesigning a process, a product, or even just a meeting format—start by asking: what would make this a truly awful experience? You’ll be surprised how quickly that unlocks clarity about what really matters.
And if you’re curious to try this exercise with your team, reach out. I’d be glad to guide you through it.