746: How to Make Small Talk with Executives, with Lorraine K. Lee

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Aug 25, 2025

Lorraine K. Lee, a LinkedIn Top Voice and author of Unforgettable Presence, shares her insights on mastering small talk with executives. She emphasizes that small talk is crucial for building deeper relationships and highlights the importance of preparation. Lorraine offers practical tips like threading conversations for balance and approaching discussions with curiosity. She also discusses overcoming the challenges introverts face in networking and shares strategies to make meaningful connections, making small talk manageable and even enjoyable.

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ANECDOTE

Embarrassing Shadowing Lesson

Lorraine shadowed a president of a major movie studio in college and felt mortified for not preparing.
The president told her to always be prepared when talking to executives, which shaped her career approach.

INSIGHT

Small Talk Powers Relationships

Small talk is often dismissed but it is one of the most powerful ways to connect if done intentionally.
Improving small talk builds relationships that form the foundation of meaningful work.

ADVICE

Index Predictable Moments

Index likely 'on-stage' moments and prepare for them instead of fearing randomness.
Expect predictable opportunities like all-hands, conferences, and customer meetings and rehearse accordingly.

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Lorraine K. Lee: Unforgettable Presence

Lorraine K. Lee is passionate about helping ambitious professionals go from invisible to unforgettable in the modern workplace. She is recognized as a LinkedIn Top Voice in workplace communication and presence and spent over a decade as a founding editor at top tech firms like LinkedIn and Prezi, where she worked on core products including the LinkedIn Daily News module and LinkedIn Newsletters. She is the author of Unforgettable Presence: Get Seen, Gain Influence, and Catapult Your Career.

Small talk. We all love to hate it – and we also know that most of us will end up in small talk with someone who’s got a lot of influence. It may be an executive or an external stakeholder. Either way, handling it well can open up doors. In this conversation, Lorraine and I detail how to make small talk go better.

Key Points

Small talk is the starting point before a deeper relationship.
Most opportunities for executive small talk are predictable. Preparation will help you speak well.
Set the tone with positive energy. Rather than dominating the interaction or passively reacting to it, thread your conversations so each party shares equally.
At the office, be ready with a sentence or two about who you work with and what you’re working on. Relationships and outcomes are more memorable than titles.
At social events, share a hobby or interest and ask about theirs. Keep questions open-ended as you would with a friend.
Have a topic ready to go for quick interactions. Sharing a thought about a book or podcast that relates to your organization is a useful resource to have at the ready.
Review your go-to topics regularly so that you always have a relevant conversation topic.

Resources Mentioned

Interview Notes

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A Key Tactic for Way Better Conversations, with Alison Wood Brooks (episode 717)

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