Undermining, defiant and disengaged direct report—coach them or cut them loose?

Dealing with a direct report who questions everything, isolates their team, and actively undermines leadership? YIKES. That’s not just frustrating—it’s a full-blown leadership headache. When radical candor turns into outright defiance, how do you respond without losing your mind (or your team’s trust)? In this episode, Kim and Amy tackle the tricky reality of managing someone who refuses to engage, blames leadership for team turnover, and resists every attempt at coaching. From figuring out whether this is a communication breakdown or a serious performance issue, to deciding if a PIP is the right move, they walk through strategies to reset expectations, shut down toxicity, and lead with confidence. Because at the end of the day, if you’ve ever thought, I literally don’t know what to do with this person, keeping a toxic presence around does more damage than having a tough talk. Get all of the show notes at RadicalCandor.com/podcast.

Episode Links:

Connect:

Chapters:

(00:00:00) Introduction
Kim and Amy introduce a manager’s challenge: a disengaged, undermining direct report.
(00:04:46) Generational Gap or Performance Problem?
Whether this is a workplace culture clash or a deeper issue.
(00:06:28) Red Flags: Undermining & Resistance
Signs of bad-faith questioning, team isolation, and leadership defiance.
(00:14:18) The Tough Feedback Conversation
Role-playing a direct, no-nonsense conversation to reset expectations.
(00:23:49) Handling Pushback & Defiance
When a direct report resists leadership—what’s your next move?
(00:26:38) PIP or Part Ways?
How to decide if coaching, a PIP, or letting them go is the right call.
(00:34:03) Emotions in Leadership
Handling a direct report who dismisses the emotional impact of their behavior.
(00:38:06) Accountability Without Micromanaging
Creating clear expectations and consequences without constant oversight.
(00:42:53) Next Steps: Coach, Challenge, or Cut Ties?
How to assess whether a direct report can grow—or if it’s time to move on.
(00:53:22) Radical Candor Tips
Balancing Caring Personally with Challenging Directly to lead effectively.
(00:55:43) Conclusion

Learn more about your ad choices. Visit megaphone.fm/adchoices

20th Century Philosophy

Mentioned by

Mentioned in 1 episodes

The AI-powered Podcast Player