A Game of Connections

Insights and Activities from August's Joyful Connection Masterclass

The August masterclass arrived loud in the best sense. Engagement rings in the chat, football season on the horizon, Hootie and the Blowfish on the speakers. Two people in the room had just gotten engaged. One person's book had just come out. The temperature was already up before anyone was asked to do anything.

Most attempts to make strangers open up work against themselves. The request is the problem. Ask someone to be vulnerable and the moment becomes about performing vulnerability rather than feeling anything real. People know what an honest conversation is supposed to sound like, and knowing makes them stiffen up.

This session avoided the request entirely.

Three of the four activities were literal games, complete with rules, guessing, winning and losing. The fourth was built the same way, with a fixed time window and a fixed number of answers. The design across all of them landed on the same insight. Rules do what direct questions cannot. They give people something to hide behind, and inside that shelter, the honesty comes out on its own.

Setting the Frame with Ryan G

Turning three defined categories into a soft way to introduce yourself

Ryan G, a play by play broadcaster who hosted this Masterclass and helps others do work they love at HelpOtherPeopleWin.com, opened with a game he has been playing at home with his youngest son. Clue.

Everyone picked a person, a place and a thing that carried meaning for them. Not Professor Plum in the conservatory with a lead pipe, but a mentor, a home, an object that mattered. In the small groups that followed, whoever was wearing the color closest to red at the start of the rainbow song went first, chose one of their three categories to share, and passed the turn on so the next person had to pick from what remained.

Ryan modeled it with all three. Mrs. Diede as his person, a teacher he named without further explanation but with real weight in how he said it. Mile High Stadium as his place, the stadium where he watched the Broncos play for the first time. Sunglasses as his object, offered almost as a joke and not one at all.

The move worked because the categories did the work of the question. Nobody had to figure out how to introduce themselves, and nobody had to summarize their life. They just picked one meaningful thing from three defined slots. The room warmed up by talking about the objects, places and people that shaped them, which is a much shorter route to being real than talking about jobs.

How to Practice It:

• Give a memory prompt with defined categories rather than an open one, since choosing from three slots feels safer than answering from a blank page
• Model your own first with something small and specific, since the size of your example sets the size others will feel free to bring
• Use a familiar frame like a game to open a gathering, so the first move feels like play rather than the start of an assessment

Turning Networking Into a Game with Shaena Harrison

Using the phone in your pocket to find the people who already connect you

Panelist Shaena Harrison, a Professional Wing Woman and the founder of Wing People, a Stockholm based collective of professional connectors, invented her activity by accident. She was at a networking event with, in her words, no coffee and no liquid courage. Instead of asking the next person what they did for work, she asked if they wanted to play a game.

The rules are small. First, partners agree on what they are playing for. Fika, the Swedish ritual of coffee and something sweet, or lunch, or dinner, or simply bragging rights. Then each partner asks the other one question. Then, without opening LinkedIn, they each write down how many mutual connections they think they have. Reveal, compare, closest guess wins. Then look at who the actual mutuals are, pick one that surprises you, and ask: how do you know them?

Benji Boehlke modeled it with her live. His question was about proximity, which he explained is one of the strongest predictors of shared relationships, so he asked where she had lived. Canada, Ireland, Scotland, Sweden. Both wrote down five. The actual number was six. They looked at the mutuals and started naming them out loud, catching that several of them were sitting in the same room. The demo landed exactly where the game was designed to land.

The point was never the number. The number is the excuse to get to the sentence that follows, which is where the small talk ends. How do you know them? That question does not exist inside a first introduction. It only exists once the map is on the table.

Shaena named the elegant edge case too. If two people have no mutual connections at all, they still leave with one more than they arrived with. Each other.

How to Practice It:

• Turn what do you do into how do you already overlap by using a shared platform as a map, so the conversation starts from something real instead of from job titles
• Ask one question first, then guess, then reveal, since a game with reveals earns attention that a straight introduction never does
• If there are no mutuals, name that the conversation itself is the new connection, since the design still works when the map is blank

Letting the Rules Do the Work with Benji Boehlke

Using a light game to skip the small talk without asking for depth

Panelist Benji Boehlke, the founder of MapChat Social, a social connection app built to turn everyday third places into somewhere people actually meet each other, opened by naming Jackbox games as what he could play for hours, and Fibbage in particular, the one where you invent a convincing lie and try to spot everyone else's. He ran an activity called Pair Play. The concept is deceptively small. A pair of options appears on the screen. Chocolate or vanilla. Pancakes or waffles. Rich in time or rich in money. You pick your own answer, then guess your partner's.

Benji framed the mechanism as mirror neurons firing, the connection that lands when you find that synchronicity between you and another person. Underneath it he pointed at the same principle Shaena had built her game on, and phrased it plainly: Games are effective because there are rules to abide by, and rules give people permission to be vulnerable without the constraints of normal societal expectations. He gestured at the well-known 26 questions to fall in love as another version of the same idea. The prompt shape does the work that direct questions cannot.

Kelly Lynn Adams modeled it with him. He picked his own answer to each pair first, then read her, guessing where she would land on questions that moved from light to a little more revealing. Chocolate or vanilla gave way to how you would rather be rich, in time or in money. The guessing was the point. Each correct read landed as a small hit of being understood, and each miss opened a reason to explain yourself, which is a conversation the pair would not otherwise have had.

How to Practice It:

• Use a light game to skip the small talk without asking anyone to be vulnerable directly, since permission arrives through the rules rather than through the ask
• Let the rules protect people, so they can be silly or serious inside the same structure without having to choose in advance
• Let the questions deepen gradually, moving from light preferences toward more revealing ones, so people arrive at honesty by degrees rather than all at once.

Measuring Backward with Kelly Lynn Adams

Naming what has already been built instead of what still needs to happen

Panelist Kelly Lynn Adams, an iPEC certified global business and life coach and the host of the Perfectly Imperfect podcast, closed the session with the one activity that was not a game. It was built like one though, with a fixed time window and a fixed number of answers. Pick a period of the last one to three years. Name one to three wins from inside it. That is the whole exercise.

The idea comes from The Gap and the Gain, which argues that high achievers spend most of their attention measuring themselves against where they want to be. That comparison always leaves them short, because the goal keeps moving. Measure backward against where you started and the picture inverts. The distance already covered becomes visible in a way it never is when you are looking forward.

Kelly Lynn modeled it with real weight. She named the consistency of her podcast since 2018, through episodes that landed with a single listener and the temptation to quit. Then she went further, into the grandmother she lost in 2023 and the best friend she lost unexpectedly in 2025. The win in both, she said, was the self trust she had built by finding a way to keep going through them.

Shaena modeled it with her, and matched the register. Wing People built into a real company across three and a half years. The Human Connection Cluster she started at Epicenter in Stockholm for neurodivergent superconnectors, the people whose brains spot patterns roughly four hundred times a day. And a personal one, that after twenty years together she and her husband had consciously uncoupled and she was living on her own for the first time.

Two women who barely knew each other took the exercise seriously and let it take them somewhere real. Neither would have shared any of that in response to “How are you doing?”. The specific frame, one to three wins across one to three years, made an opening that a general question never could have.

The takeaway line landed cleanly. Do not wait to celebrate.

How to Practice It:

• Ask for specific wins from a defined time window rather than asking generally how someone has been, since specificity does the work that a soft question cannot
• Model with something honest, including a hard win, so the people around you feel permission to name theirs at the same depth
• Point yourself and the people you lead backward as often as forward, since how far you have come is a resource most of us leave unused

Thank You

Thank you to Shaena Harrison, Benji Boehlke and Kelly Lynn Adams for designing and leading these activities, and to Ryan G for hosting the session and CultureCon for co-creating this Masterclass with us. Thank you also to everyone in the room who took the invitation seriously and gave a stranger something true to hold onto.

The session made a case worth carrying out. People do not open up because they are asked to. They open up when handed a set of rules to hide behind, whether the rules come from a game, a guessing round, or a time window with a number attached. The frame does the work. What comes out inside it is honest almost in spite of itself.

We look forward to continuing this work and to helping more people feel genuinely connected, one conversation at a time.