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What my dad taught me about talking to strangers
Published about 2 months ago • 3 min read
Hello Reader, Two weeks ago, I came across GenWell’s initiative encouraging people to talk to a stranger - a simple reminder to smile, say hello, and connect with someone new. It brought me back not only to my trainings on the art of small talk, but to my childhood itself.
My Dad and the Art of Talking to Strangers
Do you remember being told as a child, "Don't talk to strangers"? I do. And I also remember watching my dad completely ignore that advice.
Growing up, he talked to everyone - the cashier, someone in line at the bank, a person sitting on a park bench. I was embarrassed by how unabashedly he engaged with strangers.
What I didn’t understand then was that he was building something hard to come by: community, connection, and a reminder that we’re all human - all worth knowing.
Now, as an adult, I’m 100% my father’s daughter. I’m endlessly curious about people, love asking questions, and learning their stories. And small talk? It's one of the most powerful tools we have for building genuine connection. He taught me curiosity, warmth, how to notice people. He showed me how to make someone feel valued through something as simple as a genuine question.
When I heard about GenWell’s ‘Talk to a Stranger Week,’ a campaign encouraging simple greetings and conversations, it resonated immediately.
Studies suggest that even small conversations with strangers can boost happiness, foster empathy, and create a sense of belonging - all things I’ve seen firsthand in my work. These brief "micro-relationships" with others build happiness, decrease loneliness, and foster empathy, trust, and a sense of belonging. From an etiquette standpoint, this aligns beautifully. Mastering the mechanics of table settings or conversation gives confidence, but what truly sets professionals apart is genuine care. When you engage meaningfully, you give someone the chance to feel seen, heard, and valued. So two weeks ago (which coincided beautifully with Talk to a Stranger Week), we organized something where a bunch of strangers met for their first times… and it was magic. Let me tell you more.
Next Gen Meetup: Connection in Action
In the spirit of trying to understand Gen Z’s (to be able to grow in my own knowledge bank when addressing the topic of the generational divides at work), I’ve been organizing a Gen Z Coffee meetup. We keep it totally analog / in person. And this month's (our third one) was pure magic. We had eight young Gen Z’ers join us - up from just one at our first meetup - and the conversation was powerful.
I hear often that “Gen Z is impossible to manage.” But when you listen, they open up. When you respect them, they share insight. And when you’re curious, they speak honestly. They shared candid thoughts on boundaries, flakiness, AI, and leadership. Read the full conversation on my blog. The next Gen Z Professionals Coffee Meetup is Jan. 21st in Ajax. If you know anyone interested, connect them to me.
And speaking of strangers connecting... last month at Hothouse in Toronto, we brought together professionals who'd never met for a Business Dining Etiquette workshop, and the energy was incredible. Participants learned to navigate formal place settings, balance business conversation while dining, and approach business meals strategically - treating them as "meetings with food," not just social occasions.
From mastering utensil configurations to understanding host vs. guest roles, attendees left feeling confident and prepared for any professional dining situation.
"Many insights that will help me in my professional life and even in my personal life." - Workshop Participant
Interested in bringing this training to your team? Reply to this email to chat about customizing it for your organization.
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Network Like a Leader (condensed) Workshop: Dec. 10 (1-2pm)
I’ll be hosting a condensed version of my networking workshop in this free webinar. You'll discover your personal networking style, learn how to prepare strategically, and master follow-up techniques that build lasting relationships. It's designed for entrepreneurs, client-facing professionals, and managers responsible for modelling effective networking practices and developing these capabilities within their teams.
So this week, I’m challenging both of us: talk to a stranger. Smile at someone in line. Ask the barista how their day is going - and really listen. You never know what might happen.
Warm regards,
Trina Boos Founder & CEO Boost Academy of Excellence boostacademyofexcellence.com P.S. If your team is working through generational communication challenges or could benefit from stronger workplace communication skills, I'd be happy to chat about how my training modules might help. Just reply to this email.
Subscribe for tips on handling workplace challenges, building communication and social skills, and exclusive course updates. Hear success stories from professionals, perfect for young professionals and leaders aiming to sharpen their skills and foster respect.
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