How to Navigate the Messy Middle Between Ruinous Empathy & Obnoxious Aggression 6 | 49

Radical Candor: Communication at Work

How the CORE method can help you thrive in the messy middle.

Caught in the middle of a boss who’s all care but no action and a team lead who’s full steam ahead with no brakes? That’s a workplace tightrope no one wants to walk. Your ability to Care Personally and Challenge Directly can seriously be affected when communication falls apart on both ends of the spectrum, and it’s not just frustrating—it’s debilitating. How do you stay productive and keep your sanity when you’re managing up and down with people who either dodge conflict entirely or bulldoze through it? In this episode, Jason and Amy tackle the messy middle, breaking down how to use the CORE method (Context, Observation, Result, Expected Next Steps) to navigate these tricky situations. It’s not about pointing fingers or playing favorites—it’s about finding a way to ditch the drama and focus on what really matters: working better together.
Get all of the show notes at RadicalCandor.com/podcast.
Episode Links:

• Give Candid Feedback With the CORE Method | Radical Candor
• Feedback from Your Boss | Radical Candor
• Asking for Feedback | Radical Candor
• The Radical Candor Order of Operations | Radical Candor
• Make Work Less Like Jr. High: Radical Candor Podcast 5 | 10
• Managing Challenging Conversations At Work | Radical Candor
• Navigating Workplace Tensions: Stuck Between Ruinous Empathy and Obnoxious Aggression

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Chapters:

(00:00:00) Introduction
Amy and Jason introduce a listener dilemma about a ruinously empathetic boss and an obnoxiously aggressive team lead.

(00:02:15) Defining Ruinous Empathy and Obnoxious Aggression
What it means to care without challenging and to challenge without caring.

(00:04:44) It’s the Boss’s Job: Accountability Matters
Why the manager has ultimate responsibility and how to provide feedback.

(00:07:53) Raising the Issue with Your Boss
How to approach a ruinously empathetic boss with care and directness.

(00:11:46) Involving Your Boss Effectively
How to engage your boss in resolving team tensions without blame or shame.

(00:17:55) Using the CORE Method
A step-by-step approach to delivering clear and constructive feedback.

(00:20:55) Role-Play: Navigating a Clean Escalation Conversation
How to handle a tough conversation between a team member and an aggressive lead.

(00:31:11) Building Common Ground
Tips for fostering mutual understanding and creating actionable steps.

(00:34:02) Radical Candor Tips
Key takeaways and practical tips for addressing conflict.

(00:36:35) Conclusion