I'm the 'Cool' Boss and It's Not Working 7 | 19
May 07, 2025•38 min•Season 7Ep. 19
Episode description
Are you the cool boss that everyone loves, but no one respects? Join Kim and Jason as they address a pressing question from a production supervisor struggling with their team's lack of accountability. Learn the importance of sharing personal stories, soliciting feedback, and giving timely criticism, all while remembering that accountability is an act of kindness. If you're struggling with setting boundaries and holding people accountable, we've got your back.
Get all of the show notes at RadicalCandor.com/podcast.
Episode Links:
Transcript
Why Being a “Cool Boss” Backfires — And What to Do Instead
Stuck In a Ruinous Empathy Rut 5 | 11
Navigating Workplace Tensions: Stuck Between Ruinous Empathy and Obnoxious Aggression
Managing Resistance: How to Reset Expectations With Challenging Direct Reports
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Chapters:
(00:00:00) Introduction
Kim and Jason introduce a listener’s question from a self-described “too nice” boss.
(00:01:23) The Difference Between Nice and Kind
The distinction between being "nice" and being "kind" in leadership.
(00:03:13) Holding People Accountable
How accountability is a core leadership skill, not an act of cruelty.
(00:06:33) The Cost of Avoiding Accountability
Why Leadership requires addressing difficult behaviors early.
(00:11:39) Two Kinds of Respect: Earned vs. Given
The two definitions of respect and how managers can earn it.
(00:14:45) Emotional Labor of Leadership
How management is giving more than you get—by design.
(00:19:16) Confusing Strictness with Respect
Challenging the misconception that punishment creates respect.
(00:23:45) Holding Yourself Accountable
Using vulnerability to open a dialogue and reset expectations.
(00:25:44) Share Your Radical Candor Story
Sharing personal stories to introduce a cultural reset.
(00:28:27) Create a Shared Culture and Vocabulary
Advice on resetting workplace culture and team alignment.
(00:32:26) Radical Candor Tips
Actionable steps for building a culture of Radical Candor.
(00:33:24) Conclusion
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