How To Be Happy

How To Have Difficult Conversations At Work - HTBHAW #15

We all know those conversations; the ones you put off, rehearse in your head, and hope magically resolve themselves. Whether it’s giving feedback, setting a boundary, or addressing tension with a teammate or boss, tough conversations are a non-negotiable part of working well with others. But most of us were never taught how to have them.

In this episode of How to Be Happy at Work, I unpack the real reasons we avoid difficult conversations (spoiler: fear, discomfort, and people-pleasing play a big role), and share evidence-based tools to help you show up with clarity and compassion. We’ll dive into:

✅ Why Brene Brown says "clear is kind", and how vagueness erodes trust

✅ Kim Scott’s Radical Candor model, and how to challenge directly while still caring personally

✅ The psychology behind our avoidance, including fear of rejection and the nervous system response

✅ The dangers of the dreaded “sh*t sandwich” feedback method (and what to do instead)

✅ Prompts, prep tips, and real-life examples to help you navigate hard conversations with confidence

Whether you're a leader, teammate, or just someone who wants less awkwardness and more honesty at work; this one’s for you.

🎧 Listen now and learn how to make your next difficult conversation feel a little less... difficult.

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