Hello Monday with Jessi Hempel22 Sep 2025

The Likeability Trap and How to Escape It

Why does success make men more likable, but women less so? Researchers call it the success–likeability paradox, and it’s one of the biggest challenges women face as they rise in their careers. In this episode of Hello Monday, Jessi Hempel sits down with Kate Mason—executive coach, former world champion debater, and author of the new book Powerfully Likeable—to explore how women can succeed without sacrificing authenticity or influence. Kate argues that likability and power aren’t opposites. In fact, the most effective leaders know how to blend authority with connection, conviction with empathy. And with the right communication tools, we can all do the same. Jessi and Kate discuss: Why the likability–success paradox persists—and how to navigate it How women can project authority without being labeled “too much” Why over-preparation holds many leaders back (and how to stop) What executive presence really means (and why the term is flawed) Why you don’t have to minimize yourself to be liked Practical ways to build authentic influence through better communication Why failure is essential to success—and how to reframe it as experimentation If you’ve ever felt like you’re walking a tightrope between being likable and being respected, Kate offers a new way forward—one that’s rooted in communication, confidence, and authenticity. Continue the conversation with us at Hello Monday Office Hours! Join us Wednesday at 3 PM ET on the LinkedIn News page.

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