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October 23, 2025 14 mins

Tammy J. Bond shares her frustration after hearing a story from a middle manager dealing with a chaotic environment. The core issue: senior leaders are prioritizing being liked and showing misplaced "compassion" over actual leadership, accountability, and clear expectations. This episode is a fierce examination of how this dynamic demoralizes middle managers, promotes a culture of mediocrity, and actively destroys team trust and performance. Tammy challenges both senior leaders to put on the "boss hat" and middle managers to lead down and courageously speak up.

Key Takeaways for Leaders (At All Levels)

  • Chaos is Contagious, and so is Mediocrity: When leaders above the middle manager avoid difficult decisions (like performance termination), they model that mediocrity is acceptable, frustrating the rest of the high-performing team.

  • Friendship is Not a Strategy: Prioritizing feeling liked or showing "compassion" in a performance issue is a destructive leadership failure. Compassion for hurt is necessary; compassion for unacceptable performance is enabling.

  • The Cost of Circumvention: When a senior leader oversteps a middle manager (e.g., going directly to the employee or giving them assignments) it shows a break in trust, a lack of respect, and a disconnect that breaks down the entire organizational structure.

  • The 90-Day Rule: Leaders must be slow to hire and quick to fire. Performance issues should be addressed and resolved (via performance plan or termination) well within the initial 90-day evaluation period.

The Middle Manager's Survival Guide

Middle managers are often stuck: managing up, communicating down, and balancing two sides with no support. Here's how to navigate the tension:

  1. Lead Down and Pull People Closer: When the top is failing, focus your energy on your team. Allow a three-minute "whine 101" for them to voice frustration. Acknowledge, "Heard, understood," and then ask, "And now what?" to shift to solution mode.

  2. Courageously Manage Up: Do not suffer in silence. Use curiosity to address boundary violations with your boss. Try framing your question like this:
    "I'm just curious, help me understand what's missing in my management style that's causing you to go around me directly to my staff? Here's what it feels like, and here's how it impacts the team."

  3. Know When to Escalate: If the unhealthy and destructive behavior of your superior continues, you have a right to go to HR to have a conversation about the negative impact on the team and your ability to lead.

A word from Tammy: I unapologetically ask bold questions and challenge assumptions to help leaders rethink what they thought was true! If this episode resonates with you and you need help having this conversation with your boss, reshare this episode, tag me in your post, and I will reach out to discuss a role-play strategy.

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