The Art of Finding Work: Job Search: Hack Talk to Strangers

An impromptu conversation with an AI engineer, the chef of a five-star hotel writing down their lamb stew recipe for me, being told of a mechanic for my ’82 Corvette whom eight years later I still go to, advice that improved my golf game, countless “you need to connect with [person], give me your email address, I’ll e-intro you” and job opportunities. Every person you meet has something to teach you or is connected to someone that you’d benefit from knowing.    

In previous columns, I’ve pointed out that opportunities are all around you; the catch is that they’re attached to people. The person pumping gas beside you or standing behind you in a grocery store checkout line, seated next to you on a plane, in your doctor’s waiting room, or at a sporting event might be a VP, director, or head of HR at a Fortune 500 company or a business owner. 

You never know who’s next, in front of or behind you.

Think about the wealth of knowledge and opportunities surrounding you when eating in a crowded restaurant. Talking to strangers is not merely a skill; it’s a mindset rooted in openness and receptivity. It’s one of the most underrated skills for personal and professional growth. 

Many people have conditioned themselves to avoid interacting with strangers because of habit, fear of rejection, or being too preoccupied. This conditioning explains why interviews—essentially conversations with strangers—often trigger anxiety.

Starting a conversation, especially with someone you don’t know, is more art than science. It involves understanding social cues (body language, tone of voice, personal space), reading the room, and thinking creatively. As with any skill, starting a conversation becomes easier with practice. Start by having a different conversation with someone you know. Ask thought-provoking questions. Be curious. Shift the dialogue beyond the usual. 

Consider questions like:

• “What skills are essential for success in your field?”
• “What makes you think that?”
• “What have you tried?”
• “What’s your end goal?”
• “Do you think you could improve if you had [whatever]?”

Asking open-ended questions and being genuinely curious about the other person—showing interest in someone is a massive gesture—often leads to meaningful conversations.

Here are three simple yet effective ways to take advantage of our tendency to love sharing what we know and who we are, which can lead to job opportunities, expanding your network, friendship, mentorship, and maybe even love.

Give a Compliment

A genuine compliment about a unique watch or handbag can break the ice and lead to discussions about personal interests and career paths. For example, saying, “That’s a nice watch! Mind my asking where you got it?” might open a dialogue revealing that the watch owner works at a large accounting firm—just the connection you need as an accountant seeking opportunities.

Alternatively, you can wear or carry something unique that attracts attention to you so you’re receiving compliments. (read: strangers starting a conversation with you) When I take my ’82 Corvette for a spin, I always get strangers asking about my car. Once, an admirer of my car turned out to be the president of a pizza chain who was facing challenges with his call center’s customer service. I ended up doing some consulting work for him after explaining my background. 

Ask for a Recommendation

Shared spaces like restaurants, sporting events, and doctor’s waiting rooms create a sense of commonality. You can assume everyone in line with you at a sushi restaurant likes sushi as you do. When you’re in a coffee shop, bookstore or new to a town or neighbourhood, leverage this commonality; don’t hesitate to ask a stranger for recommendations on a good book or where the best BBQ ribs are to be had. Asking a stranger in a bookstore’s historical fiction aisle, “I’m looking for a new book to read; do you have any favourites?” may result in discussing your reading interests and perhaps what you do for a living.

Engage with Humor

Victor Borge once said, “Laughter is the closest distance between two people,” which is why I like to use humour to engage strangers. A light-hearted comment, such as, “If this line gets any longer, I might as well order a coffee for my great-great-grandkids!” fosters camaraderie and stimulates conversation.

The key to these conversation starters is authenticity. Genuine engagement resonates with people, making them more likely to participate in meaningful discussions. Focus on starting and building relationships—the essence of networking. Don’t be that person who, upon learning what I do for a living, asks, “Can you get me a job?” Avoid the mindset of “What can I get from this person?” Instead, ask yourself, “How can I help this person?” as I did when I met the president of the pizza chain.

Offering assistance is the most effective way to establish a bond with someone.

Most importantly, give your full attention. Pocket your smartphone, maintain eye contact, listen actively, and show interest. Although engaging with strangers at first seems daunting, the rewards can be substantial. There’s no telling what a simple conversation could lead to that could benefit your job search, career, or other aspects of your life.

Nick Kossovan, a well-seasoned corporate veteran, offers “unsweetened” job search advice. Send Nick your job search questions to artoffindingwork@gmail.com