Leadership Insights

The Pattern That Doesn’t Look Like a Problem  

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Preview — The Kindness That Isn’t Kind

Recognize the pattern by what it produces over time, not by the intention behind any single choice.

Think about someone on your team that you’ve been supporting through a performance challenge. You’ve extended a deadline when the work wasn’t ready. You’ve softened the feedback so that it would land better. You’ve coached them through the same issue more than once, privately, because naming it directly felt like it would damage something between you.

None of that feels like avoidance. It feels like care.

But if the situation hasn’t improved—if you’re still having the same quiet conversations six months later, still absorbing consequences on their behalf, still explaining their gaps to the rest of the team—something else is happening. The support has stopped being support. It’s become a structure that holds the problem in place.

What Enabling Actually Looks Like

Most leaders who fall into this pattern don’t recognize it because the individual behaviors are reasonable on their own. What signals that the line has been crossed is the pattern over time, including:

  • Perpetually extended deadlines. One extension is flexibility. But a continuous pattern of extensions is a message that the deadline doesn’t really apply.
  • Feedback that disappears in the softening. When you work so hard to make criticism land gently that the actual message no longer survives, you haven’t had the conversation yet.
  • Repeated private coaching without naming the pattern. Coaching someone through a problem is good supervision. Doing it repeatedly without ever saying “this is a pattern I’m concerned about” is a different thing entirely.
  • Making excuses upward. When you find yourself explaining or minimizing an underperformer’s gaps to your peers or to your own supervisor, you’ve started absorbing accountability that belongs to them.

How does your Five Paths profile play into this? Leaders operating from the Relator path are most prone to this trap: their instinct to protect relationships and shield people from discomfort is genuinely rooted in care. But the enabling pattern shows up across all the paths, just in different ways. A Warrior may skip the hard conversation and simply do the work themselves, which removes the consequence entirely. A Visionary may perpetually reframe the underperformance as a development opportunity without ever anchoring it to real consequences. The trap is path-specific, but it’s not path-exclusive.

The instincts driving these behaviors aren’t the problem. Where those instincts are being directed is.

Pause & Reflect

Think of someone you’ve been “supporting” through a persistent performance gap. Has your support been moving the situation forward or holding it in place? The honest answer to that question will determine your next steps.

Pro Tip

Take this to Sophia. Try: “I’ve been supporting someone on my team through a performance issue for a while. Help me think through whether my support has been moving things forward or keeping things stuck.”

Learn more about holding individuals accountable in the Advanced Supervision Certificate program. The next cohort starts September 28.