How to Navigate Challenging Conversations with Confidence episode artwork

EPISODE · Sep 15, 2025 · 23 MIN

How to Navigate Challenging Conversations with Confidence

from The Drop In CEO · host Deborah Coviello

In this solo episode of the Drop-in CEO podcast, host Deb Coviello shares personal updates and dives deep into the art of navigating challenging conversations with confidence. Deb introduces a practical framework for handling difficult discussions, explores why these conversations are often so tough, and emphasizes the importance of language and empathy. Through relatable stories from both family and business, Deb equips listeners with actionable strategies to improve their communication and leadership skills.   Episode Highlights The Framework for Challenging Conversations [10:39]Deb outlines a step-by-step framework for approaching difficult conversations, focusing on establishing common ground, identifying gaps, and taking mutual action. Why Challenging Conversations Are Difficult [7:30]An exploration of the emotional and systemic reasons that make tough conversations so challenging, and why most organizations don’t teach these essential skills. The Power of Language in Difficult Conversations [13:27]Deb discusses the importance of word choice, empathy, and respect in maintaining relationships and moving through workplace challenges. Personal Connection and Icebreaker [2:00]Deb opens the episode with personal stories and updates, setting a relatable and engaging tone for the discussion.   For more information about my services or if you just want to connect and have a chat, reach out at: https://dropinceo.com/contact/See omnystudio.com/listener for privacy information.

Episode metadata supplied by the publisher feed · Published Sep 15, 2025

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