I recently sat down with a group of new hires as part of our onboarding program (s/o @Ranna who's been driving these), and someone asked: what's one piece of career advice I'd offer the group. I shared a mental model I've used for the past decade on how to actually connect with folks: treat every person you meet as a different board game.
Before I get into what that means, I want to say why I think about connection this deliberately. It's never come easily or evenly for me. With some people, it's instant, you sit down and the conversation just flows, no translation required. With others, something is off from the first exchange. You can't quite tell what it is. Maybe the conversation stalls in places it shouldn't, or it just feels a little cold. And let's be honest, you probably gravitate toward the people where things flow and drift from the ones where they don't. That's normal. It's also friction that's baked into how differently people are wired, the kind that quietly stalls collaboration and erodes trust.
At work, that one-on-one connection is the atomic level of every relationship. We just don't call it that. When the same gap shows up between two people, we usually blame something bigger: a functional boundary, sales versus engineering, product versus finance. But it starts with two people who never quite figured out how to connect.
Leadership research actually has a name for the org-level version of this: boundary spanning, the practice of building working relationships across departments and hierarchy levels instead of only staying effective inside your own team. In practice, that looks like a sales leader sitting with the engineers who built the product before ever pitching a customer, or a finance leader learning how product actually decides the roadmap instead of just auditing the result. Most senior executives call it one of the most important skills a leader can have, and almost none rate themselves good at it. When people ask me how I've grown as a leader, this is the honest answer: years of forcing myself to go learn someone else's board game instead of waiting for them to learn mine.
Meeting people in their own game
So what do I actually mean by treating someone like a board game? I once had a colleague who ran circles around every conversation with data. Charts, benchmarks, a number for everything. My instinct runs more conceptual, I think in high level strategy and objectives, wanting to understand the bigger picture. Every meeting with him felt like a slog until I stopped waiting for him to meet me halfway and just learned his game: showed up with the numbers pre-loaded, let him poke holes in them, and only then made my actual point. Once I did, we went from talking past each other to actually building things together. That's the whole idea. Everyone has their own rules, their own strategy, their own way of playing. Connecting with someone very different from you can feel like learning a new game from scratch, awkward at first, like speaking two different languages. That's exactly where most people give up.
So how do you cut through it?
Learning the rules of each game
Picture every person as different board games, and think of communication as two people sitting down to play a board game – typically one that they represent. Say I'm Monopoly*, my favorite. My teammate is Chutes and Ladders. To connect, we need to play something together. Most people default to proposing their own game, because that's the one they're good at. One person ends up with the advantage while the other is stuck learning the rules mid-conversation. They don't know the core strategy of the game and how to win. How can they possibly perform well? Notice that dynamic the next time you're talking to someone who doesn't "speak" your game.
This is where "meeting people where they are" stops being a phrase on a values slide and turns into an actual decision. In that exact moment, you either make them learn Monopoly or you go learn Chutes and Ladders yourself. I've sat across from engineers who think in systems and edge cases when I'm trying to talk strategy. The fastest way to lose them is making them translate everything into my language first. So I go learn how they think instead, and meet them there.
There's a power dynamic hiding in this that's worth naming, especially if you're the one with more authority in the room. When a leader defaults to their own game, the other person doesn't really get to say no. They'll learn Monopoly whether they want to or not, because you're the one running the meeting. That's the version of this I try hardest to catch in myself. The more senior you get, the easier it becomes to make everyone else do the learning, and the less likely they'll be able to successfully connect with you.
Now flip it. What if I took the time to actually learn Chutes and Ladders, so the next Chutes and Ladders type I meet, I already know how to play with them? Now I've got two games in my back pocket. Stretch that out far enough and think about how valuable that makes someone: able to communicate with nearly anyone in the org because they took the time to learn everyone else's game first.
Not my first game of Checkers
Here's the part that took me longer to see: the games repeat. You'll meet a Monopoly player in your first job, and a decade later, in a completely different company, you'll meet another one. Same instincts, same blind spots, same way of pushing for control early and defending it. You've probably said the sentence yourself without realizing what it meant: "I used to work with a guy just like him." That's your game repeating itself. Once you've actually learned a game, you don't relearn it from scratch. You just recognize the board. I've walked into rooms with people I'd never met and known almost immediately how they'd want to be pitched, pushed back on, or persuaded, because I'd played their exact game with someone else years earlier. That recognition compounds. It's one of the few skills that gets cheaper to use the longer you've been working.
Compare that to the alternative: everyone only plays their own game and refuses to learn anyone else's. You almost never end up with an org of all Monopoly players. What you get instead is a bunch of people standing at the edges of each other's boards, unwilling to sit down and learn the rules, and instead just playing their own games. Alone. Collaboration gets harder. Silos show up, not because anyone planned them, but because nobody found a way to actually play together.
So when you're meeting someone new, default to learning their game instead of teaching them yours. It costs you more up front, you won't be as sharp, you'll ask more basic questions than you're used to. But every game you actually learn becomes something you carry into the next team, the next company, the next person who reminds you of someone you already know how to play with. That's what boundary spanning looks like once you stop treating it as a leadership competency and start treating it as a habit, one relationship at a time.
I haven't mastered this. I still catch myself defaulting to Monopoly when I'm tired or rushed. But every time I catch it and choose differently, I end up with one more game in my back pocket, and someone across the table who didn't have to do all the work to connect.
Also, it's just fun.
*Side note: While Monopoly is my favorite game, I really play a version of Monopoly that my family created. We altered the rules, created additional monopoly cash, extended the assets beyond houses/hotels and extended into estates and resorts. Games would last years.