3 Lessons from conversations with strangers

I launched a networking campaign to discover the next step in my vocation, relying wholly on the goodwill (and trust) of individuals to introduce me to someone or take time to meet with a complete stranger. I’m 10 meetings in, and each one has been wildly different.

“So sorry, I didn’t prep at all for this, who are you again?” is how one meeting began, but it ended with a hug. Other conversations felt like well-intended interrogations to help solve all my problems. Topics have ranged from faith, to luck, to ethics, to risk, to prayer, but each conversation has contained a unique lesson in the art of conversation.

Context matters. Hence the, “Who are you again?” moment. It’s one thing to skim an AI summary before you jump into the virtual meeting room, it’s another thing to approach a stranger and greet them with a smile, a handshake, and a question that initiates a verbal dance. Most of my conversations have taken place over a table with coffee in hand, only some over the shouting of a street preacher, but the context has influenced each one — things as broad as the physical environment to things as specific as the timing of sharing information. Like a chain reaction, each sentence moves the conversation in a different direction.

Attention, the type of attention, also matters. On either side of a conversation, I have begun to distinguish between understanding and knowing. Sometimes, a person wants to understand my situation, my intentions, my reasoning. Other times, a person wants to know my desires, my values, my passions. Neither are wrong, but either posture can feel misplaced — you can tell when the energy starts to leak out of the room. Given the right context, you can also tell what the speaker wants to give — understanding or knowledge — and shaping a conversation around those things becomes the goal.

Courage is the arguably the most important lesson I’ve learned. Courage to be wrong, courage to ask questions, courage to look stupid. Above all, courage to be yourself. Not in an individualistic way, but in an honest one. People intuit far more than they understand, and honesty, confidence, and humility go a long way in building trust. Trust paves the way for vulnerability to be reciprocated, which some people genuinely long for. If not, no harm no foul. Courage means you’re playing your game, honestly — not someone else’s.

Conversation is like a sport. Success requires endurance, art, and skill. But the best conversationalists probably don’t see it that way. Conversation is not a means to a successful end or a game to be mastered; in its purest form, conversation is a pathway to curiosity, hospitality, and connection. When the participants forget themselves in lieu of the other, the conversation begins to feel like a dance.

My goal began with 50 conversations, but now I hope it turns into many more relationships. Most of these conversations won’t scratch the surface. Still, there is depth to a person worth attending to. There are stories with weight that have formed the person sitting across from me, and stories yet to be told that will shape the person they become. Along with stories of my own, I find comfort in the fact that we are all part of a bigger story, one that I hope to behold one day, perhaps over a cup of coffee.