The Messy Middle: What Happens When We Skip the Hard Conversations

A client came to me recently, visibly frustrated. “I think I need to let them go,” she said. “They’re just not doing their job.” 

But as we dug deeper, it became clear: This wasn’t a clear-cut termination issue. It was a hard-conversation-avoidance issue. 

The employee was underperforming, with deadlines being missed, follow-through inconsistent, and basic responsibilities slipping through the cracks. But there was something missing before jumping to the “final step”: No one had ever told them these things. Not directly. Not clearly. Not kindly. 

Most leaders don’t mean to avoid accountability conversations — but it happens. 

• Maybe it’s a fear of confrontation. 

• Maybe it’s a hope that the employee will eventually “get it.” 

• Maybe it’s a belief that being a “nice boss” means being accommodating. 

• Maybe it’s the fear of not knowing how to handle it if the employee pushes back. 

• Maybe it’s the lack of confidence of knowing how to address the struggles.

Unfortunately though, ignoring the problem doesn’t make you kind. It makes you unclear. And unclear leadership breeds confusion, resentment, and lost potential. 

I call this the Messy Middle. It’s full of awkward yet important conversations, repeated clarifications, and vulnerable coaching moments. But it’s also where growth happens, for the employee and the leader. 

When we go straight from frustration to termination without walking through the steps in between, we miss opportunities to: 

• Clarify expectations and rebuild accountability 

• Understand root causes (is it skill? motivation? personal life? misalignment?) 

• Offer coaching that could spark real change 

• Demonstrate integrity in how we handle challenges 

The “Messy Middle” Steps Every Leader Needs 

Instead of jumping from silence to severance, here’s what the Self-Aware Leader does: 

1. Pause & Reflect: Ask yourself: Have I been clear? Have I been direct? Have I provided the tools for success? 

2. Have the Hard Conversation Early:  Address concerns as soon as patterns emerge, not when resentment boils over 

3. Acknowledge Specific Strengths:  Acknowledge genuine, honest, and observable strengths. Don’t globally tell them, “You’re doing GREAT! Keep up the Awesome work!” then silently bemoan their short comings. 

4. Be Specific & Compassionate:  General feedback like “you’re not doing your job” shuts people down. Say what’s missing, why it matters, and what needs to change, with kindness. 

5. Offer Support & Boundaries: Set goals, offer coaching, and check in regularly. But don’t carry it all for them. 

6. Document, Don’t Just Hope: Track conversations, follow-ups, and improvements. This isn’t just CYA, it’s about accountability and fairness.

7. Set a Clear Path, Up or Out:  At some point, if change doesn’t happen, you’ll know you gave it your best effort. And the employee will know they had every chance to rise to the occasion. 

Leadership isn’t about choosing between being nice or being firm. It’s about being clear, courageous, and compassionate — especially when it’s uncomfortable. 

Accountability is a form of care. Avoidance is not. 

Reflection Questions for the Self-Aware Leader:

1. What feedback have I been avoiding, and why? 

2. Have I given my team the clarity and coaching they need to succeed?

3. What might change if I committed to the “messy middle” instead of fast-forwarding to the end?

If this resonates and you’re facing a leadership moment where the “messy middle” feels unclear or overwhelming, feel free to reach out. I’d be glad to help you navigate it with clarity, confidence, and care.

YOU MATTER!