Oliver was a leader I worked with who was painfully awkward in most social interactions. He had great technical depth and could hold his own in digging through the details. But it was as if his brain kept making a detour around any personal interactions.
Part of it was that he respected people’s time and dove right in. He was probably an introvert who dreaded small talk and pleasantries, finding them pointless. When meetings began, he jumped straight to business. No pleasantries, no catching up or conversation about what people had been doing. He wasn’t rude,. just efficient. There was work to do and he wanted to get to it.
The challenge was, people didn’t know him. And because he was the leader, he set the tone for the interactions. There wasn’t much discussion or participation. He felt stiff, so the meetings felt stiff. People didn’t contribute and counted the minutes until they were over. I always found his meetings uncomfortable. It was hard to get conversation going when he tried to quickly move through the agenda.
As Oliver advanced in his career, a coach pulled him aside and encouraged him to be more personal. To engage people as humans instead of jumping straight into meetings. He was given one rule: before jumping into the agenda for the meeting, he had to share something about himself. It could be an article he read. A podcast he listened to. Something he did over the weekend. It just couldn’t be about work or the meeting.
I could tell right after he got the coaching. Each meeting started with something like “My wife and I went to a new restaurant last night.” Then he’d describe what they ate or some interaction with the wait staff.
You could almost see him checking a box on his mental to-do list.
Tell a story. ✓
Be social. ✓
Then he'd move on to the meeting. It was so obvious what he was doing, and it was forced. He was way outside of his comfort zone. These moments were awkward.
And they totally worked.
People asked him questions. They shared things about their own lives. The tone of the meetings began to change. Even though it was forced and awkward, people responded to the humanity of it.
Oliver hadn't suddenly become a charming conversationalist or mastered small talk. He certainly wasn’t going to host a masterclass in charisma. But his deliberate effort to show the person behind the title and give them something to connect with.
We Underestimate the Small Stuff
I'm not a fan of small talk. As an introvert, I dread exchanges that feel meaningless. I don't want to be forced into sharing something interesting about myself, and I don't think every meeting needs a round of personal updates.
I've come to appreciate the difference between small talk for its own sake and making an effort to connect with another person. When we're busy, it's easy to treat the human parts of work as optional. We have an agenda to cover, a decision to make, a problem to solve. Every minute spent chatting can feel like a minute taken away from the work.
Especially when we're leading people, we can convince ourselves that efficiency means getting straight to the point. But think about what happens when you enter a meeting with someone who knows very little about you. They know your role, your expectations, and perhaps your reputation. They don't yet have much else to go on.
A small personal detail gives them another way to understand you. It offers an opening for a question, a shared experience, or a moment of recognition. People start connecting and relating, and discussions become a little less transactional. The way you begin an interaction can make it easier for people to engage in the first place.
You Don’t Have to be a Natural
I talk about Oliver often when people question whether to use stories, even small ones like Oliver’s. They protest they aren’t good at it and I tell them how Oliver was stiff, wooden, and awkward. And that made him more real, vulnerable, and endearing. His effort was impossible to miss, and his brief stories made him more approachable and invited engagement. Oliver was probably aware that he was stilted and may even have felt a little ridiculous. And he did it anyway.
We often assume that meaningful connection should happen naturally. If we're not comfortable with small talk, we skip it. If telling personal stories feels forced, we keep them to ourselves. If we're not naturally warm, we rely on being competent and assume people will eventually see the person behind the work. Sometimes they do. Sometimes we make it harder than it needs to be.
You don't have to become an extrovert or turn every interaction into a personal conversation. You can be intentional about creating openings for connection, even if the behavior doesn't come naturally to you.
That might mean sharing something you found interesting, asking a colleague about something they mentioned last week, or taking a moment to acknowledge what someone has been working through before diving into the next assignment. The point is to show enough interest in the person that a relationship has room to develop.
Connection is Part of the Work
This matters most when you're asking people to trust you, navigate uncertainty, or work through something difficult. If the only time people hear from you is when you need something, your interactions can start to feel purely transactional.
You can't manufacture trust with a weekend anecdote. And if your actions contradict your words, no amount of personal sharing will make up for it. Small moments can establish a different pattern of interaction and signal that the relationship matters.
Sometimes, the things that make the biggest difference are the small things we choose to do consistently, even when they feel awkward.
***
Karen Eber is an award-winning author, TED speaker, and storytelling keynote speaker. She is the author of The Perfect Story and her TED Talk on how the brain responds to stories has been viewed more than 2.25 million times. As CEO and Chief Storyteller of Eber Leadership Group, she helps leaders communicate ideas that inform, influence, and inspire.
