A man who taught social skills for a living left Nick Bendel cold and a shy stranger who’d just moved to Australia left him completely won over. After six years and 500 lunches with strangers, the speaker, author and social courage expert explains what really makes a conversation work.
As an EA, you spend your career having conversations. Not just lots of them but lots of different kinds too. One moment you’re speaking with a CEO, the next with a client, supplier, board member, graduate or someone you’ve never met before.
You already know every conversation is different. What fascinated me after six years of having lunch with 500 strangers was discovering why some conversations felt effortless while others never quite clicked.
As a lifelong introvert who found networking uncomfortable, I decided to challenge myself by having lunch with 500 strangers over six years. I met everyone from CEOs and politicians to tradies, teachers, students and retirees. While the project was designed to stretch my own social confidence, it also became an unexpected masterclass in conversation.
Start with curiosity, not cleverness
One lunch taught me this lesson better than any book ever could. I met a man who taught social skills for a living. Ironically, he left me feeling cold. He seemed to be speaking from a script and paid little attention when I spoke.
A few weeks later, I met a shy woman who had recently moved to Australia. She didn’t have polished techniques or rehearsed stories. Instead, she listened closely, asked thoughtful questions and responded with genuine interest. She made a far stronger impression.
That experience changed my understanding of conversation. The best conversationalists aren’t usually the most entertaining. They’re the most curious. Rather than trying to impress people, they make other people feel interesting.
- As an EA, that’s a subtle but powerful shift. Thoughtful questions and genuine listening often reveal priorities, concerns and opportunities that might otherwise remain hidden.
Adapt to the person, not the title
Another lunch reminded me that good conversation isn’t about expecting everyone to communicate the way you do.
The woman I met had a mind that seemed to move a million miles an hour. She would begin one story, suddenly jump to another and then circle back without warning. At first, I kept interrupting to clarify where we’d landed. Eventually, I realised I was disrupting her natural rhythm.
So I changed my approach. Instead of trying to organise the conversation, I let it unfold in whatever direction she wanted to take it. Almost immediately, our rapport improved.
That’s a lesson I’ve seen repeated hundreds of times. Some people enjoy exploring ideas, while others prefer practical details. Some think carefully before speaking, while others think out loud. The goal isn’t to find one perfect communication style. It’s to recognise the style of the person in front of you and meet them there.
- As an EA, you do this instinctively every day. The more consciously you adapt to different personalities, the easier it becomes to build trust across every level of an organisation.
Remember that everyone has an invisible story
One of the biggest surprises from my 500 lunches came long after one particular conversation had ended.
I’d had a wonderful lunch with a CEO. She was articulate, engaging and seemed completely comfortable. We stayed in touch and met again several times. Then, during a later text exchange, she admitted she’d been incredibly nervous before our first lunch because she’d been bullied as a child and had struggled with social confidence for years. I was stunned and I’d never have guessed.
That conversation reinforced one of the most important lessons from my project: every person carries an invisible story. Some have experienced encouragement and belonging. Others have experienced rejection, criticism or exclusion. You rarely know which is which.
That’s why I’ve become less interested in judging people’s behaviour and more interested in understanding it. Someone who seems abrupt may simply be overwhelmed. Someone who appears confident may be feeling anxious. Someone who seems quiet may simply need more time to feel comfortable.
- As an EA, you’re often the first point of contact for people entering an organisation. Approaching every interaction with empathy rather than assumption doesn’t just make conversations better. It makes relationships stronger.
After 500 lunches, I’ve come to believe the conversations that truly click have very little to do with status, personality or finding the perfect words. They happen when people feel heard, understood and valued.
Master that, and you’ll master the art of conversation.
nickbendel.com
