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 Russ brings the fire with his “gravity assist slingshot” method—forget the outdated career ladder, it’s time to propel people toward their real ambitions.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

Connect:

• Website
• Instagram
• TikTok
• LinkedIn
• Facebook
• YouTube

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

Russ Laraway breaks down why your leadership isn’t working—and how to fix it.

Stuck in a cycle of vague goals, half-hearted feedback, and meaningless career talks? Let’s call it what it is—bad leadership. In part one of this two part episode, Kim, Amy, and Russ Laraway rip into the mistakes that are killing your team’s engagement and results. Russ brings the heat with his “Big Three” leadership essentials—direction, coaching, and career—and doesn’t hold back on why so many managers fail to deliver. Why are leaders so scared to prioritize? Why do career conversations feel like an empty HR theater? And why does feedback either go ignored or turn into a dreaded confrontation? If you’re ready to ditch the excuses, face the hard truths, and lead with real purpose and impact, this episode is your wake-up call. It’s time to step up, get clear, and transform the way you lead—before it’s too late.

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

Connect:

• Website
• Instagram
• TikTok
• LinkedIn
• Facebook
• YouTube

Chapters:

(00:00:00) Introduction
Kim and Amy introduce Russ Laraway and the "Big Three" of leadership.

(00:03:00) What Are the Big Three?
Russ explains the framework of direction, coaching, and career.

(00:07:24) The Flintstones House
Kim and Russ share stories about the unique office space of Candor Inc.

(00:10:31) Defining Direction in Leadership
The importance of clarity in expectations and ruthless prioritization.

(00:15:11) Long-Term Leadership Tools
How managers can collaboratively define purpose and vision.

(00:17:24) Crafting Team Goals and Priorities
Setting measurable goals and the role of weekly prioritization.

(00:26:12) Purpose and Vision Statements

Examples of vision statements and their impact on team alignment.

(00:31:43) Coaching for Engagement
Coaching elements that drive employee engagement.

(00:33:29) The Book and Specific Praise
Using praise to motivate teams and reinforce standards.

(00:38:59) Soliciting Feedback from Teams
The importance of creating a culture where feedback flows both ways.

(00:43:53) Leadership and Power Dynamics
Strategies to balance authority and empower team collaboration.

(00:45:25) Radical Candor Tips
Practical tips for applying direction, coaching, and career insights.

(00:47:29) Conclusion

What happens when you gut the glue holding your team together.

Is middle management really dead weight, or are we cutting off the wrong limb? In this episode, Amy and Jason take on the hype around “The Great Flattening” and call out the risks of gutting the layer that keeps organizations running smoothly. Sure, middle managers have their flaws—what role doesn’t? But eliminating them entirely isn’t the brilliant shortcut some leaders think it is. They dig into how this trend often creates chaos, undermines team engagement, and leaves critical gaps in communication and strategy. Spoiler: quick fixes and vague promises of efficiency don’t replace the value of solid leadership and strong relationships. With sharp insights and actionable advice, this conversation is a wake-up call for anyone buying into the flattening trend without a second thought. Skeptical? Maybe. But sometimes you need a little tough love to see what’s really at stake.

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

Episode Links:

• What Do Managers Of Managers Do? | Radical Candor Podcast S4, Ep.16
• Who Wants To Be A Manager? | Radical Candor Podcast S6, Ep.14
• Should I Be A Manager? | Radical Candor Podcast S5, Ep.25
• Middle Manager Hiring Has Plunged, And Those Jobs May Never Come Back | Business Insider
• Don’t Eliminate Your Middle Managers | HBR
• Amazon's Great Un-bossing: Why Eliminating Middle Managers Could Hurt Employee Engagement 😮
• It’s Time To Rethink The Role Of The Middle Manager | Mckinsey
• The Resurrection Of The Middle Manager | Achurch
• Heroes Or Villains? Recasting Middle Management Roles, Processes, And Behaviours | Tarakci
• The Hidden Risks Of Eliminating Middle Managers: A Critical Insight
• Mass Layoffs Often Hit Middle Managers. The Cuts Are Largely Short-Sighted | BBC
• Who Wants To Be A Manager? | Radical Candor Podcast S6, Ep.14
• The Measurement Problem | Radical Candor Podcast S3, Ep.7
• How To Get Shit Done | Radical Candor Podcast S4, Ep.2

Connect:

• Website
• Instagram
• TikTok
• LinkedIn
• Facebook
• YouTube

Chapters:

(00:00:00) Introduction
Jason and Amy introduce the topic of eliminating middle management.

(00:02:17) The Great Flattening Explained
The trend of eliminating middle management roles in organizations.

(00:05:37) Blaming Middle Managers
Why middle managers are often seen as costly and ineffective.

(00:10:00) The Role of Middle Managers
The role middle managers play in strategy, coaching, and alignment. 

(00:15:21) Risks of Flattening Organizations
The unintended consequences of cutting middle management.

(00:20:10) Case for Middle Management
Tips for demonstrating the value of middle managers to leadership.

(00:25:29) Redefining Middle Management
How organizations can reshape the role to meet modern demands.

(00:33:11) Radical Candor Tips
Practical tips for navigating The Great Flattening.

(00:35:07) Conclusion

Tech’s “meritocracy” is broken—Ellen Pao unpacks how to fix it.

Alright, let’s get real—tech’s so-called “meritocracy” is doing more harm than good, and it’s time to face it head-on. This week we’re bringing you an episode of the Radical Respect podcast. Kim and Wesley sit down with Ellen Pao, founder of Project Include, to dig into how the industry’s obsession with merit often masks deep-seated bias, exclusion, and outright harassment. Ellen doesn’t hold back as she breaks down why quick fixes (we see you, generic unconscious bias training) just don’t cut it, how unchecked bias erodes trust and psychological safety across teams, and the way Project Include is leading the charge with real strategies for change. From CEOs stepping up to own their role in DEI to addressing the messy realities of AI in the workplace, this conversation is all about building environments where everyone has a shot. Ellen’s story is packed with takeaways for anyone who’s struggled to balance compassion with calling out the tough stuff, and is ready to challenge the status quo and build workplaces where it’s better to have a hole than an asshole.

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

Episode Links:

• Project Include
• Data & Society — Ellen Pao
• @ekp.bsky.social on Bluesky
• Reset: My Fight for Inclusion and Lasting Change

Connect:

• Website
• Instagram
• TikTok
• LinkedIn
• Facebook
• YouTube

Chapters:

(00:00:00) Introduction
Kim and Wesley introduce Ellen Pao, founder of Project Include.

(00:01:37) The Genesis of Project Include
How Project Include started and its impact on improving workplace inclusivity.

(00:05:25) Challenges of Virtual Workspaces
The increase in bias and harassment in virtual work environments. 

(00:06:38) Meritocracy and the Tech Industry
The role of meritocracy in shaping tech’s culture and DEI challenges.

(00:09:24) Overcoming Resistance to DEI
Data-backed methods for fostering DEI support among skeptics.

(00:13:46) DEI as a Business Imperative
The importance of CEO involvement in creating and sustaining DEI initiatives.

(00:19:50) Balancing Morality and Market Pressure
How leaders can make ethical decisions that align with DEI principles.

(00:25:31) Governing AI in the Workplace
Key considerations for ethical and inclusive AI adoption in workplaces.

(00:28:33) Social Media’s Role in Amplifying Harm
The need for accountability in curbing online hate and misinformation.

(00:37:26) Impactful Investments in DEI-Focused Ventures
Stories of innovative ventures improving equity in healthcare and workplaces.

(00:41:27) Conclusion

Ditch the drama and rebuild connection where it counts.

Feeling overwhelmed by workplace polarization, the loneliness epidemic, and the constant whirl of change? You’re not alone—and neither are your teams. In this episode of Radical Candor, Kim and Amy bring in Heather McGowan, future-of-work strategist, to dig into why we’re so divided and distracted at work—and what leaders can actually do about it. Heather gets real about the deeper roots of these challenges, from shifting demographics to technology’s relentless pace, and shares her signature brand of practical, no-nonsense advice for fostering respect, empathy, and collaboration. It’s not about ignoring differences or plastering on a quick fix—it’s about creating the kind of human connections that help teams thrive. Learn how to lead with intention, listen to what’s not being said, and ditch the divide in favor of working better together.

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

Episode Links:

• Heather E. McGowan - ImpactEleven | LinkedIn
• Heather McGowan
• Navigating the once a century shifts: cultural, social, demographic, technical, and economic
• Loneliness Epidemic is Leaving Us Distracted and Divided
• Managing Post-Election 2024 Tension At Work 6 | 43
• I Never Thought of It That Way: How to Have Fearlessly Curious Conversations in Dangerously Divided Times
• Bowling Alone: Revised and Updated: The Collapse and Revival of American Community
• The Adaptation Advantage: Let Go, Learn Fast, and Thrive in the Future of Work
• The Empathy Advantage: Leading the Empowered Workforce
• Loonshots: How to Nurture the Crazy Ideas That Win Wars, Cure Diseases, and Transform Industries
• Braver Angels
• The No Asshole Rule: Building a Civilized Workplace and Surviving One That Isn'tThe Least of Us

Connect:

• Website
• Instagram
• TikTok
• LinkedIn
• Facebook
• YouTube

Chapters:

(00:00:00) Introduction
Kim and Amy introduce the episode’s focus on workplace polarization with guest Heather McGowan.

(00:02:12) Why We’re Divided
The societal and workplace factors fueling polarization.

(00:06:42) Balancing Rights and Income Inequality
The interplay between workplace equity and broader societal trends.

(00:09:02) Short-Term Thinking in Leadership
How short-term decisions undermine long-term organizational health.

(00:12:03) Intentional Conversations Across Divides
Practical tips for engaging with diverse perspectives meaningfully.

(00:16:21) Finding Common Ground at Work
Building relationships through shared experiences and lighthearted topics.

(00:22:12) Drawing Ethical Boundaries
Knowing when to disengage while maintaining openness elsewhere.

(00:26:32) The Future of Work and Learning
Why adaptability and continuous learning matter more than ever.

(00:33:46) Loneliness in the Workplace
Combating workplace isolation with intentional connection and empathy.

(00:41:27) Embracing Discomfort and Curiosity
Why great leaders lean into questions, not answers.

(00:45:53) Radical Candor Tips
Start conversations, focus on humanity, and take small steps to connect.

(00:49:10) Conclusion

Everyday actions, when turned into rituals, can manage emotions and create a sense of meaning.

Amy Sandler is joined by Harvard Business School Professor Michael Norton to discuss his latest book, The Ritual Effect. Norton explores the significance of rituals in reducing stress and enhancing productivity, both at work and in personal life. He shares compelling research and personal anecdotes that illustrate how everyday actions, when turned into rituals, can manage emotions and create a sense of control and purpose. The conversation covers the practical application of rituals in business settings, their emotional significance, and how they can foster team cohesion and workplace wellness. Whether you're a skeptic or a believer in the power of rituals, this episode offers valuable insights into how structured routines can lead to greater emotional health and professional effectiveness. 

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

Episode Links:

• Michael Norton
• Michael Norton’s Books
• Harvard Business School Profile
• Michael's Paper on Humblebragging
• Michael's Paper on Matchmaking
  
• Rituals Quiz | What Are Your Rituals? | Michael Norton

Connect:

• Website
• Instagram
• TikTok
• LinkedIn
• Facebook
• YouTube

Chapters:

(00:00:00) Introduction
Amy Sandler introduces guest Michael Norton and his book The Ritual Effect.

(00:02:16) A Quick Ritual Exercise
A fun and engaging ritual exercise to explore emotional connections.

(00:04:18) From Skeptic to Advocate
Michael’s journey from being a ritual skeptic to writing The Ritual Effect.

(00:07:40) The Meaning of Rituals
How rituals naturally emerge to provide structure and meaning.

(00:10:04) Rituals vs. Habits
The emotional difference between habits and rituals.

(00:12:13) Rituals as Emotion Generators
The dual role of rituals in generating and managing emotions.

(00:15:05) The Power of Collective Rituals
How shared rituals strengthen bonds and create collective experiences.

(00:16:30) Rituals at Work
Examples of team rituals that foster bonding and purpose.

(00:20:46) Fostering Meaning in Teams
Balancing team pride and inclusivity when designing rituals to reflect shared values.

(00:23:38) Creating Work Rituals
Advice for leaders to cocreate rituals for new work teams.

(00:26:24) Adapting Rituals for Remote Work
How teams have developed virtual rituals to maintain connection online.

(00:29:05) Meaningful Rituals in the Workplace
The significance of rituals in the workplace for individuals and leaders.

(00:32:54) Evaluating the Benefits of Rituals
How rituals contribute positively to mental health and well-being.

(00:36:49) Leaders Supporting Organic Rituals
Tips for leaders to encourage authentic rituals without imposing corporate mandates.

(00:39:59) Aligning Rituals with Team Values
Using rituals to express and reinforce organizational values creatively and authentically.

(00:41:50) Discovering Your Rituals
Exploring the rituals in your life through Michael’s Ritual Quiz.

(00:45:21) Conclusion

Practicing Radical Candor with your family members this holiday season.

Holiday communication with your family can be rife with stress. And while you love your family, let’s be frank, family togetherness during the holidays often goes sideways. So much so that it’s become a trope that’s spawned dozens of holiday movies. But you can survive it by practicing Radical Candor with your nearest and dearest this holiday season to avoid defaulting to Obnoxious Aggression, Manipulative Insincerity or Ruinous Empathy.

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

Episode Links:

• Applying Radical Candor To Dysfunctional Family Dynamics
• 7 Ways Radical Candor Transforms Relationships, According To ChatGPT
• A Happy Marriage Of Growth And Stability | Radical Candor
• Radical Candor – Speaking Directly and Caring Personally – The Veterinary Idealist
• The Overton Window – Mackinac Center
• How to Use Radical Candor to Communicate Clearly With Your Family During the Holidays

Connect:

• Website
• Instagram
• TikTok
• LinkedIn
• Facebook
• YouTube

Chapters:

(00:00:00) Introduction
Kim, Jason, and Amy introduce the topic of navigating difficult family dynamics during the holidays.

(00:02:53) Radical Candor and the Holidays
The struggle with practicing Radical Candor with families during the holidays.

(00:04:36) Generational and Cultural Differences
How cultural and generational gaps complicate family communication.

(00:07:12) Family Role Expectations and Childhood Patterns
Reverting to childhood behaviors and role expectations during family visits.

(00:9:18) Taking the Bait: Avoiding Escalation
Strategies for turning down conversational "volume" and avoiding conflict bait.

(00:20:20) Overreacting to Advice
How understanding intent can improve family dynamics.

(00:24:37) Why Gifts Sometimes Backfire
The alternate perspectives on gifts dependant on the giver or receiver.

(00:27:42) Gifts Gone Wrong
Personal anecdotes of gift-giving mishaps and lessons learned.

(00:33:33) The Strain of Gift Giving
How gift giving can be especially hard in strained family dynamics.

(00:35:59) Setting Boundaries with Family
Asserting personal boundaries when saying yes takes its toll.

(00:39:22) Gifting with Intent
Releasing the obligation of the perfect gift for the giver and receiver.

(00:43:51) Radical Candor at Family Gatherings
Guidance on when to lean into Radical Candor and when to let things slide.

(00:50:12) Appreciating Moments Together
The finite nature of time with loved ones and making the most of family gatherings.

(00:54:51) Radical Candor Tips
Tips on setting boundaries, practicing care, and avoiding unnecessary conflict.

(01:00:01) Conclusion

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

Connect:

• Website
• Instagram
• TikTok
• LinkedIn
• Facebook
• YouTube

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

Showing respect when you just don’t connect.

Ever feel like caring about a coworker is just...not in the cards? Same. Here’s the thing though – you don’t have to be besties to show respect and keep things productive. In this episode, Kim, Amy, and Jason tackle the tough question of how to Care Personally when someone’s driving you up the wall. With relatable stories (yes, even a deodorant conversation makes an appearance) and practical tips, they break down how to stay curious, address frustrations head-on, and avoid letting those "ugh" feelings spiral into toxicity. The key takeaway? Stop writing mental soap operas about your colleagues and start having real conversations. Awkward? Sure. Worth it? Absolutely.

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

Episode Links:

• What It Means to Care Personally About Your Team
• What's the Ideal Manager-Employee Relationship?
• What does it mean to Care Personally?
• How to Develop Empathy for Someone Who Annoys You
• What Is Radical Respect? Learn Why It's Crucial for a Healthy Workplace Culture
• Beware The Fundamental Attribution Error: Radical Candor Podcast 5 | 8
• How to Give Difficult Feedback While Still Caring Personally
• Adam Grant | Instagram
• How to Care Personally About Someone You Don’t Like
• How to Care Personally When You Don’t Like Someone

Connect:

• Website
• Instagram
• TikTok
• LinkedIn
• Facebook
• YouTube

Chapters:

(00:00:00) Introduction
Kim, Jason and Amy introduce ​​a listener’s question about caring personally for someone you don’t like.

(00:02:09) Radical Respect
How respect forms the core of caring personally, even when someone annoys you.

(00:03:48) Reframing Perspectives
Reframing narratives to foster empathy in difficult workplace interactions.

(00:05:05) Addressing Irritating Behaviors
Two stories from differing perspectives on personal irritations at work.

(00:08:17) Curiosity as a Bridge
The power of curiosity in understanding and seeing humanity in others.

(00:11:02) Unspoken Disagreements
How assumptions and unspoken disagreements corrode relationships.

(00:14:16) Repairing Relationships at Work
The journey from conflict to rebuilding a strained relationship with a peer.

(00:22:17) Different Work Styles
Respecting differing approaches to work and optimizing collaboration.

(00:24:14) The Role Self-Awareness
Self-awareness and transitioning from internal frustration to constructive dialogue.

(00:33:08) Indifference vs. Engagement at Work
The inefficiencies of emotional detachment from colleagues.

(00:34:29) Balancing Connection and Boundaries
Maintaining professional relationships while respecting personal boundaries.

(00:37:38) Radical Candor Tips
Key tips from the episode, including respect, curiosity, and addressing biases.

(00:40:24) Conclusion

Tune in to the Radical Candor Podcast to learn to love your job and kick ass at work without losing your humanity by practicing the principles of Radical Candor. Host and Lead Radical Candor Coach Amy Sandler leads discussions with Radical Candor Author and Co-founder Kim Scott and CEO and Co-founder Jason Rosoff about what it means to be Radically Candid, why it’s simple but not easy to Care Personally and Challenge Directly on the daily, and why it’s worth it.