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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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This episode cuts straight to the heart of why difficult conversations so often go sideways for managers. It’s not just about saying the wrong thing—it’s about starting from the wrong mindset. Managers either avoid the talk entirely or come in too hot, trying to prove a point instead of seeking clarity. The result? Trust erodes, engagement drops, and the issue never really gets fixed.
You’ll learn why your approach to tough conversations either builds connection or creates disconnection—and how to shift from defensiveness to curiosity. This episode introduces a better framework rooted in calm, outcome-first thinking. If you want to lead conversations that actually lead to solutions, this one's for you.
Episode Timestamps
00:00 – Why most managers fail at difficult conversations 01:30 – Avoidance vs. aggression: the two common traps 03:14 – How tolerating issues trains your team to ignore standards 05:02 – The invisible damage of unresolved tension 06:47 – Outcome-first thinking: the mindset shift that matters 08:19 – How curiosity changes the conversation 10:12 – The new playbook: ask, don’t assume 12:07 – Creating safety in high-stakes conversations 14:23 – Recap: Calm leadership, clear outcomes 15:40 – Grab the free ebook: The Roadmap to Difficult Conversations
Links:
Claim your free copy of The Roadmap to Difficult Conversations
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