Small Talk with Big Impact: Building Authentic Connections in Business and Beyond

How do you feel about small talk?

We’ve all had those moments where seemingly innocent chit chat feels more challenging than expected. Even simple topics like the weather, sports, or weekend plans can feel loaded with the fear of judgment.

It’s not just about exchanging pleasantries; it’s about revealing a part of ourselves and quietly wondering:

“Will they think less of me if I don’t share the same sentiments and interests?”

The Pressure to Conform

We’re often nudged into fitting in, whether it’s showing just the right level of excitement for the Christmas season or getting swept up in the latest sports events.

There’s an unspoken expectation to say the ‘right’ thing, to fit into what’s considered ‘normal.’ But here’s the thing: normal is subjective.

Our unique interests and perspectives are what make conversations so rich and diverse. Yet, those same differences can leave us feeling vulnerable, wondering if we’re being judged.

Finding Joy in Different Places

Reflecting on recent conversations, through the summer I’ve noticed how people often have completely different feelings about the same things. Some thrive in the summer, soaking up every moment of sunshine, while others really dread the hotter months, finding the heat unbearable and longing for the cool, crisp days of autumn.

Where are you going on holiday?

Take holiday plans, for example. I used to be jetting off to Ibiza or exploring the wild landscapes of Iceland. These days, though, my breaks look quite different.

With an array of animals to care for, I find joy in the simple pleasures—pottering around outdoors, doing chores on my smallholding and around the stables, and spending time with furry and feathered friends.

It know it’s not about conventional excitement; it’s about what brings genuine happiness but sometimes I wonder if this lifestyle sounds a bit strange. Spoiler when I share more on this, people are usually genuinely interested.

A Gateway to Deeper Connection

When handled with authenticity and openness, small talk can open the door to more meaningful conversations. It can create a sense of safety and comfort, allowing us to express a full range of emotions.

Talking openly about what excites us, what makes us happy, and even what challenges we’re facing helps build real connections where we feel supported, uplifted, and seen.

 Engaging in inclusive, genuine small talk creates an environment where others can feel comfortable to be themselves, too. 

Small Talk and the Founder’s Journey

In the entrepreneurial world, small talk is more than just idle chatter; it plays a crucial role in building relationships with investors, partners, and customers.

These initial conversations often set the tone for future business dealings.

They are opportunities to establish trust, find common ground, and connect beyond the surface.

Pressure To ‘Fit In’ As A Founder

Founders are often shown a narrow vision of what it means to be successful – relentless hustle, back-to-back meetings, always being the charismatic go-getter.

It can feel like there’s a right way to talk, act, and even think to fit into certain entrepreneurial circles.

These interactions can feel particularly challenging if you feel like an ‘outsider’ – whether it’s due to differences in social class, gender, cultural or professional background, lifestyle choices, personal responsibilities, or unique interests. 

It’s definitely something to consider if you are an organiser or facilitator of such gatherings and events – how can you curate an environment where people to feel more comfortable, included and at ease?

Neurodivergent Entrepreneurs

Research shows that a significant number of entrepreneurs are neurodivergent—some studies suggest up to 40%.

For neurodivergent individuals, small talk can be even more challenging.

The subtle social cues and unspoken rules often feel confusing and overwhelming, amplified by the pressure to mask and conform to societal norms.

Is is Okay Not to Be Okay?

What if you’re exhausted from the relentless demands of business or dealing with a difficult personal situation?

There’s often a pressure to always be okay, to put on a brave face in business conversations when asked the inevitable “how are you?”. But not everyone feels positive all the time, and that’s perfectly normal.

Creating space for honesty in small talk, where it’s okay to say, “Actually, things are pretty rough right now,” is incredibly powerful. 

Being real about our struggles doesn’t make us less; it makes us human.

And it opens the door for genuine support and deeper connections.

Tips for Making Small Talk More Enjoyable

Here are some things I have found to be helpful.

💡Find Shared Interests: Look for common ground by noticing details say on someone’s website or a recent LinkedIn post. Bringing up a shared interest can make the conversation flow naturally. 

💡 Ask Open-Ended Questions: Questions like, “Tell me about what you’ve been working on lately?” invite the other person to share freely, making the conversation feel less forced.

💡 Be Honest: If it feels safe, acknowledge if situations involving small talk with strangers makes you uncomfortable. This honesty can lead to more genuine exchanges and a stronger connection. You might even bond over being thrown together in a zoom break out room!

💡 Set Boundaries: If certain social interactions drain you say no and focus on events or conversations that align with your interests and communication style.

💡 Find your tribe: Being in the right environment, where you feel more able to be open and vulnerable can lead to more meaningful conversations, deeper rapport, and lasting connections. It’s unlikely every setting will be your cup of tea but when you find a place that’s your vibe in it will be worth it!