Conversational Baseball
This year, I've been going to more baseball games. It isn't a conscious goal of mine, and I didn't wake up and think, "I need to see more Yankees games", but I've been to Yankee Stadium a few times this season to see my Red Sox play (and win twice!). Getting to enjoy a cold drink on a beautiful summer night while singing stadium anthems for a few hours is the perfect summer activity, and I'm glad that I've come around to doing it more often. Anyway, I had this thought while on a hike in Kálfafell, about the relationship between America's Pastime and what makes for a good conversation. Let me explain.
In baseball, a lot of the tension comes from the pitcher's mound and the moments before the baseball reaches home plate after the throw. It's in this moment that the player at bat needs to make a decision: do they swing, or stand? For many players, I bet it feels really good when they're confident that they can hit a pitch. It's as Warren Spahn said, "Hitting is timing. Pitching is upsetting timing." When the timing is right and the ball is mid-flight, crushing a 400 foot heater to right field feels like a dream come true. Back to my original point, when's the last time you felt like you had the perfect reply to someone's comment in a conversation? When's the last time you hit a home run?
Conversations between two people can be seen as a baseball game, where each person takes a turn being the pitcher and the batter. This isn't to say that to be a good conversationalist you need lightning fast reflexes (although, cleverness and quick wit are often admired), but you do need to have an arsenal of different "pitches" and hitting strategies. Unlike real baseball, there is no score. Your shared goal is flow; a good game.
As a pitcher, your objective is to throw pitches your partner can square up. As batter, you swing to keep the inning going. Good pitchers in the conversational league create hittable prompts and invite stories instead of one-word answers. In the same regard, good batters offer a clear swing (short story, opinion, or question-back). They use specifics, feelings, and reply with questions that can effectively "pass the bat", as it were.
If we'd like to take this analogy even further, here are a few more comparisons we can draw:
- Fastball (down the middle, safe, broad, quick to hit)
- “How did you land in [city/company]?”
- Changeup (gentle twist on a common opener)
- “What’s something you thought would be hard this year that turned out easy?”
- Curveball (invites story via a constraint or scene)
- “If we were meeting a year from now and it had been a great year, what happened?”
- Slider (either/or specificity)
- “Are you more ‘museum Sunday’ or ‘trail Sunday’?”
- Knuckleball (playful oddball, low-stakes)
- “What’s your most controversial mild food take?”
- Bunt (tiny prompt that gives them the plate)
- “Say more?” / “How’d that feel in the moment?”
- Pickoff (return to a thread they dropped earlier)
- “You mentioned a second startup; what did you carry over from the first?”
- Intentional Walk (give them space to monologue)
- “Take your time, start wherever makes sense.”
- Mound Visit (meta/tempo control)
- “Can I switch gears for a weird question?” / “Want to stay in this topic or wander?”
Last but not least, since we're playing for flow, you should keep a few "home run" pitches in your back pocket. A 65-mph fastball right down the middle. These are prompts/questions that rely on light, respectful in-group cues, and are intended to immediately build rapport. One example that came to mind: my old college/NYC roommate is from New Jersey, Central Jersey to be exact. Jersey residents are divided over whether they recognize central NJ as its own region, and it's a bit of an inside joke. Whenever I meet someone new from NJ, after asking their name and other pleasantries, I like to follow up with: "By the way, are you from north, south, or central jersey?" Nine times out of ten, they'll respond with a bit of a snicker, whether they're from central ("and yes, we exist!") or not ("north, and everybody knows central jersey isn't real!"). The pitch sets them up to talk about something they're likely passionate about (their home state), the hit is clean, and the conversation flows easier when they feel like you know something about them.
This doesn't need to be region-specific. I mean, you can ask people from The Bay Area about the name of the Fog where they live for a similar reaction (it's Karl), but the idea is that your home run pitches come from actually listening to people and learning what they are excited to talk about. As a pitcher, you can establish flow by throwing a few test pitches and see what works well. Or if you find yourself at bat first, not every question needs to be met with a home run. A smooth pop fly in the conversational league will actually help more than a brazen swing.
But when you find yourself at the plate, and someone just threw a pitch that's right in your strikezone, there's nothing better than making perfect contact and watching the game go on. The best part is that unlike traditional baseball, we're all on the same team, especially when it comes to talking to one another and learning from each other.