What 500 Lunches With Strangers Taught About Leadership

Why Social Courage Comes Before Confidence For six years, Sydney-based journalist and marketing agency founder Nick Bendel invited complete strangers to lunch, one at a time, driven by curiosity. The experiment was not a client-building exercise or a formal study. He wanted to test whether the discomfort of approaching people he didn’t know might pass. After more than 500 lunches, he had a book and a changed view of how confidence develops. Bendel had assumed he needed to feel comfortable before he could approach strangers. Instead, he found that confidence followed action. “I took action while I was still uncomfortable, repeated it hundreds of times and gradually became more confident,” he said. In other words, confidence is not a prerequisite for doing something difficult; it can be what repeated practice leaves behind. He distinguishes confidence—believing you can handle something—from social courage: being willing to do it even when you are not sure you can. That difference matters when a leader is delaying a hard conversation, an unconventional pitch, or a request for help until they feel ready. Bendel’s six-year experiment points to another way forward: act while uncertain, then let experience build confidence. Social courage is not certainty that things will go well; it is willingness to begin without that certainty. How Leaders Can Practice Authentic Connection Achievement and confidence can look like proof that someone has no doubts. But, as Bendel found in conversations with accomplished strangers, impressive résumés can conceal insecurity. People may emphasize their credentials not out of arrogance, but from a need to establish their worth. Comparing someone else’s polished exterior with your own private uncertainty can make you feel outmatched, even when the other person has doubts too. Authenticity, Bendel argues, isn’t a fixed personality trait or a performance of openness. It’s built through small, repeatable choices: admitting when you don’t know something instead of bluffing, asking a question because you’re genuinely curious, and naming a real concern rather than performing composure. Those choices help people feel like participants, not an audience. That approach also offers introverted leaders a way to build relationships without pretending to be extroverts. Bendel remains an introvert after more than 500 lunches; he didn’t change his personality, but expanded the behaviors he was willing to practice. Leaders can start by initiating one conversation or invitation while still feeling uncomfortable. The aim isn’t to become more outgoing. It’s to become more willing to reach out as yourself. Curiosity, Listening, and Better Conversations Nick Bendel began his 500 lunches thinking he needed to become more interesting. He eventually realized that being interested mattered more. Trying to impress someone turns attention inward: you wonder what to say next or whether you sound intelligent. Genuine curiosity eases that pressure and helps create a better conversation. One simple habit makes curiosity visible: ask follow-up questions. The first question may get a conversation started, but a follow-up shows you listened to the answer. Rather than treating conversation as an interview questionnaire, Bendel sees it as a series of doors; listening helps you decide which one to open next. A relevant response, a remembered detail, or a noticed contradiction signals that the other person is being treated as a participant, not an audience. Conversation can also do what information in finished form often cannot: invite examination. Bendel describes a neuroscientist friend who asks why when he states an opinion. The question makes him consider the reasoning behind his beliefs. Sometimes he finds it sound; sometimes he recognizes an assumption he cannot defend and changes his mind. Curiosity, then, is not just a way to connect. It can help people test what they believe and revise it. Why Human Connection Matters in an AI-Driven Workplace As AI takes on more analytical and technical work, human connection becomes more important, not less. The technology can help people research, analyze, prepare, and communicate, but eventually a person still has to act: challenge an assumption, deliver difficult feedback, or put forward an unpopular idea. Social courage is the willingness to take that step without knowing in advance how it will go. As technical friction falls, leaders may need to become more willing to navigate the human friction that remains. Relationships also create opportunities that are difficult to predict or measure. Bendel’s lunch with someone who had once worked for former Australian Prime Minister John Howard did not appear to have a clear payoff. Eighteen months later, after maintaining the relationship and doing a few small favors, Bendel’s contact was glad to pass along Howard’s office address when Bendel wanted to invite him to lunch. The office politely declined, but that was not the point: the earlier connection had opened a door Bendel could not have anticipated. Organizations focused on measurable returns may undervalue such relationships. Yet an unclear timeline or spreadsheet value does not mean a connection has no value. Social courage helps people make those connections—and leaves room for unexpected possibilities.