Want a High-Performing Team? Let Them Play (Strategically)
By Laura Khalil
I spent 15 years inside some of the most innovative companies on the planet, working alongside the brightest people in business and technology, building products we all use today. Fortune 500 boardrooms. Cutting-edge startups. Teams with PhD-level expertise and eight-figure budgets. And underneath all that intelligence, there was an all too familiar pattern:
Someone with the critical insight stays quiet in the meeting.
Silos form between departments that should be collaborating.
Deadlines slip for reasons everyone knows but no one names.
Big goals get heaped onto already maxed-out schedules, and the team just... nods along publicly, while privately trying to find the escape hatch.
These weren't strategy problems. The strategy was usually brilliant. They were trust problems. And here's what I learned: You cannot solve a trust problem with another personality assessment, a training webinar, or a trust fall in a conference room.
We don't ask football teams to perform without practice. But we expect teams to navigate high-stakes conversations, give difficult feedback, challenge authority constructively, and collaborate across competing priorities, without ever creating a low-stakes environment to practice these behaviors. People need a training ground where they can try new approaches, make mistakes, and build muscle memory for the skills that matter most.
That's why I founded Once Upon a Roll. I use tabletop role-playing games to help teams truly build trust, communication, creative problem-solving, and genuine psychological safety.
Why Games Work When Workshops Don't
When you play a character, you get psychological distance. It's safer to try behaviors you'd normally avoid and speak up when you disagree. The game becomes cognitive training in a low-stakes environment. And what you practice in play shows up when the stakes are real.
Here's what that looks like in practice.
Recently, I ran a strategic play session with executive coaches, play researchers, and organizational consultants. All people who already use experiential methods in their own work. I had them play as elderly women solving a murder mystery.
Welcome to Granny D&D.
The Method Behind the Granny D&D Madness
Before I brought role-playing games into professional settings, I had to solve a pretty big problem: traditional Dungeons & Dragons (D&D) is too complicated. The rulebooks, character sheets, and math create barriers before you even begin. I needed something that would immediately disarm people. That would give explicit permission to be ridiculous, to try something unfamiliar, and to look silly without risk.
I found my answer in Brindlewood Bay — a tabletop game about elderly women in a mystery book club who solve actual murders. Murder, She Wrote meets collaborative storytelling. I simplified it even further, so that it’s accessible to someone who has never touched a game before, and built in a few mechanics to encourage the Five Pillars of Strategic Play: Adaptability, Belonging, Communication, Diverse Perspectives, and Empathy. When everyone is silly together, not playing along becomes harder than just going with the flow.
Each player created their granny: a name, a backstory, a cozy hobby.
Then came a crucial design element. We have each player add items to another character's purse. A witch received a grimoire. A cryptozoologist got a thermal-imaging Polaroid camera. A former bank teller received a collapsible Mighty Ducks hockey stick keychain. It sounds trivial. But that small collaborative act creates instant co-ownership. Individual stories become shared and now they’re invested in each other’s success.
We played for two hours, investigating the murder of the town's wealthy matriarch.
What Emerged Without Being Taught
Strategic play doesn't teach lessons through lecture. It creates conditions where patterns become visible:
Decision-making with incomplete information. We theorized about the murder without examining the body or meeting all the suspects. Teams do this constantly—make critical decisions with gaps in knowledge, but rarely practice the skill of saying, "We have enough to move forward." In the game, they had to make that call. Then we reflected on how it felt and what made them comfortable or uncomfortable with uncertainty.
Unspoken hierarchy. Cheryl, playing her first role-playing game, said something revealing: "I wasn't sure what I was allowed to do, so I watched first until I felt I had permission to play.” When team members are unsure of what to do, they look to others for guidance and cues. Sometimes that's useful, and other times it holds us back. Knowing when to distinguish between the two is critical.
Organic collaboration. When one player investigated a room, others instinctively helped—offering tools, creating distractions, building on observations. Natural teamwork emerged when competition was removed from the equation.
Creativity from constraint. Each character received a handful of items in their purse that they could use during the game. That limitation sparked creativity. Pearl's old bank vault keys, Lucinda's grimoire, Dorothy's jerry-rigged Polaroid camera, all became essential tools in unexpected ways. Teams with fewer resources often innovate faster than those with unlimited budgets. The game proved why.
The Moment That Revealed the Depth
In our reflection session, I asked questions designed to help players integrate what they'd learned during the game.
One player, Joe, had created Dorothy Brownstone — an 88-year-old cryptozoologist on a lifelong quest to prove the existence of the mythical sunbird of Brindlewood Bay. A creature with vibrant magenta plumage that sounded "like a trumpeting kazoo." To everyone in town, Dorothy was eccentric. A little ridiculous. The kind of person you smile at politely.
Joe sat quietly for a moment, then said something that stopped the entire room:
I think I've been hunting the sunbird in my real work. For years, I've been the researcher insisting that games belong in leadership development. It used to feel ridiculous. Now people invite me to conferences to share it. The sunbird is real.
Joe didn't realize how his professional journey had seeped into his character until we began to explore our character motivations. This is what strategic play does: It creates enough psychological distance that we can see patterns we're too close to notice.
Brian, another participant, captured why this works when conventional approaches don't:
A lot of times when people bring D&D to work, they can't translate it. What Laura did is that perfect mix—improv is too vulnerable, D&D is too complicated. This moves it just a little away from direct vulnerability, so we can act as wayward grandmothers and get out of the way of our egos.
What This Means for Teams
Studies show that teams perform better after collaborative gameplay.
Organizations are increasingly seeking alternatives to personality assessments and trust falls because those tools don't create actual behavior change.
Strategic play works because it trains the nervous system, not just the intellect. You can't think your way into psychological safety. You have to feel it, practice it and build the muscle memory for speaking up, handling uncertainty, and collaborating without ego.
Teams already have the skills and capability. The next step is fostering the training ground for teams to practice showing up differently.
Laura Khalil is the founder of Once Upon a Roll, where she uses strategic play to build high-performing teams within organizations ranging from technology leaders to startups. She has spoken at organizations such as NASDAQ, Creative Mornings, and Startup Week.