Why most career conversations fail—and how to make them actually matter.

Are career conversations a game-changer, or just another corporate mirage? In part two of this two-part episode, Kim, Amy, and Russ Laraway cut through the fluff and expose why most career talks fail before they even start. Managers love to preach growth, but when it comes to actually helping their people build meaningful careers, too many fall flat. Russ brings the fire with his “gravity assist slingshot” method—forget the outdated career ladder, it’s time to propel people toward their real ambitions. Why do leaders dodge these conversations? Why does “career development” feel like an HR buzzword instead of a real priority? And what happens when you actually invest in your team’s future? No sugarcoating here—if you’re ready to stop playing it safe and start leading with impact, this episode is your wake-up call.

Get all of the show notes at RadicalCandor.com/podcast.

Episode Links:

• When They Win, You Win
• Russ Laraway On How To Be A Great Manager  | Radical Candor Podcast 4 | 7
• How To Win At Managing - 3 Core Principles
• Stop Overcomplicating It: The Simple Guidebook To Upping Your Management Game
• “When They Win, You Win”: Russ Laraway Unpacks His New Guide For The Modern Manager
• Eagles' Sirianni Is A Players' Coach, No Matter What You Think Of Him | ESPN

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Chapters:

(00:00:00) Introduction
Kim and Amy welcome back Russ Laraway to discuss career conversations.

(00:00:52) The Gravity Assist Slingshot
Russ’s framework for career growth and thinking beyond promotions.

(00:04:51) Why Managers Should Invest in Careers
How helping employees grow improves retention and engagement.

(00:09:35) The Three Career Conversations
A step-by-step guide to drive meaningful career development.

(00:14:20) Life Story Conversation
How past career pivots reveal deep-rooted motivations.

(00:20:52) Avoiding Pitfalls and Gotchas
Where leaders go wrong in the career development framework.

(00:25:25) Framing Career Conversations
Framing the life story conversation to build trust and respect boundaries.

(00:30:51) Finding True Career Vision
An outline of helping employees set bold, authentic goals.

(00:34:26) Supporting Unconventional Goals
How managers can turn unconventional career goals into actionable steps.

(00:43:43) Career Action Plan
Turning career aspirations into progress with a clear, strategic approach.

(00:46:27) Radical Candor Tips
Where managers should start in Russ’s career conversations framework.

(00:48:14) Conclusion