Helping Leaders Get Better at Small Talk

Making small talk easier

It’s usually introverts who say they don’t like small talk.

That’s because introverts tend to prefer conversations with depth and meaning.
They like to go deep — either into their work or into real connection with others.
So small talk can feel superficial, irrelevant, or a bit forced.
And for many, there’s also a quiet worry underneath: what if I don’t know what to say next?

I listened to a podcast recently with Lorraine K. Lee, where she was talking about her book Unforgettable Presence.
One idea really stayed with me — her take on small talk.
She described it not as filler or fluff, but as a genuine leadership skill.

That same day, I was coaching a leader who, like many I coach, said she hated small talk.
She felt she had to do it as part of her role, but it didn’t come naturally.
She found herself avoiding client events, conferences and networking because of it.

As we talked, she realised it wasn’t the conversation she disliked — it was the superficiality of it and not knowing what to say next.

So I shared with her Lorraine Lee’s idea of conversation threads.
It’s a simple way to make small talk feel natural, helps you go a bit deeper, and provides a way to keep the conversation going.

Here’s what it looks like:
Instead of asking, “How was your weekend?” (which usually gets a polite, “Good thanks — how was yours?”), try:

“What was the highlight of your weekend?”

Now there’s a thread — something the other person can pull on.
Maybe they’ll say, “I went for a long walk in the hills.”
You can follow it: “That sounds brilliant — is that something you do often?”
And on the conversation goes, a bit deeper, with threads you can each pull on to keep it going.

A few reflections for HR and L&D leaders

When you’re developing leaders who don’t like small talk, help them reframe it as a deliberate leadership behaviour — not a distraction, but a simple, practical tool for connection.

You might:

  • Share how conversational threads make small talk easier.
  • Encourage them to plan for small talk: how will they answer the most likely small talk questions in a way that provides a thread?
  • Remind them that curiosity matters more than charisma.
  • Share that introverts are often excellent at this — because they listen well.

Leaders don’t need to fill the room or have something clever to say — just showing up with genuine interest is enough.

Sarah Robertson

I help leaders develop themselves and build aligned, high-performing teams.

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