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Ever felt stuck between speaking up to your boss and protecting your career? You're in a meeting, your boss makes a decision you know is wrong, but you stay silent—worried that disagreeing will make you look insubordinate or damage the relationship. Here's the truth: you're not alone. 76% of employees avoid workplace conflict, and nearly 24% of all workplace conflict happens between employees and their direct supervisors.

This episode tackles the biggest challenge middle managers face: how to disagree with your boss without getting fired. You'll learn practical strategies for managing up, navigating upward conflict, and advocating for your team while protecting your career.

What You'll Learn:

  • How to push back on decisions using clarification instead of confrontation
  • What to do when you're not getting support from your boss (it might be bandwidth, not neglect)
  • The critical documentation step when you fundamentally disagree with a decision
  • How to recognize when your boss is truly the problem—and when it's time to walk away
  • Real story from Colby's 20+ years in healthcare leadership about managing up during a budget crisis

Key Takeaways:

  • The "clarification approach" for disagreeing without seeming confrontational
  • Why coming with solutions (not just problems) changes everything
  • The follow-up email strategy that protects you when decisions go wrong
  • When to walk away from toxic leadership situations

Featured Statistics:

  • 76% of employees avoid workplace conflict whenever possible (Source: Zippia)
  • Nearly 24% of workplace conflict occurs specifically between employees and their direct supervisors (Source: CPP Global)

Perfect for: Middle managers, directors, VPs, and team leads who need to navigate upward conflict, manage up effectively, and advocate for their teams while working within organizational power dynamics.

Resources Mentioned:

Need Help Managing Upward Conflict in Your Organization? Colby works with leaders and teams through keynote speaking, executive coaching, and leadership training to build people-first cultures where difficult conversations lead to better outcomes, not damaged relationships.

For Executives: Want to create an environment where your leaders feel safe disagreeing with you? Let's talk about building that culture.

How to Support The Things Leaders Do:

  • Subscribe on Apple Podcasts, Spotify, or your favorite podcast app
  • Leave a 5-star review
  • Share this episode with a leader who's stuck knowing their boss is wrong but not knowing what to do about it

Keep advocating for your team. Keep navigating with strategy. Keep protecting your integrity. Because those are the things that leaders do.

Related Topics: Managing up, upward management, how to disagree with your boss, workplace conflict resolution, difficult conversations with leadership, navigating power dynamics, middle management skills, leadership communication, managing upward conflict, when to leave a toxic boss

#TheThingsLeadersDo #PeopleFirstLeadership #LeadershipDevelopment #MiddleManagement #ManagingUp #UpwardManagement #DifficultConversations #WorkplaceConflict #LeadershipSkills #LeadershipPodcast #ConflictResolution #ProfessionalDevelopment

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Chapters

1. Purpose And Promise (00:00:00)

2. The Fear Of Pushing Back (00:00:39)

3. Scenario 1: Clarify Or Reframe (00:02:17)

4. Scenario 2: Assume Bandwidth (00:05:15)

5. Scenario 3: Disagree And Align (00:10:55)

6. Scenario 4: When Boss Is The Problem (00:14:02)

7. Key Principles Recap (00:18:04)

8. Services, CTA, And Closing (00:18:39)

112 episodes