Experience Is Quietly Blinding Your Strategic Judgment
Joshua H. MIller

Experience Is Quietly Blinding Your Strategic Judgment

Here's why you should care:

The professional asset most prized in executive selection—deep industry experience—often becomes a liability in turbulent environments. Leaders with decades of pattern recognition feel confident, but confidence is not the same as accuracy. In fact, INSEAD conducted a study on disruption found that executives with the most experience were 32% less likely to spot new threats and 47% more likely to consider innovations irrelevant. What you’ve mastered can become what blinds you.


The trap that’s killing performance:

You assume that because something worked before, it must be reliable now. Meetings become echo chambers of “best practices” from ten years ago, and fresh ideas are labeled “risky.” Instead of scanning for contradictions, you default to the familiar. Over time, this creates strategic stagnation—your organization doesn’t fail dramatically, it just slowly loses relevance.

What you're missing:

Experience provides useful context, but it also encodes hidden biases. Without deliberately surfacing them, you mistake habit for wisdom. Exceptional leaders treat their experience as both an asset and a constraint—valuable background that must be tested against new realities.


Your bias-break strategy:

🔹 Apply the Contradiction Test

  • • Build a “challenge cabinet” of people with opposing worldviews
  • • Schedule rotating briefings from fringe voices and emerging players
  • • Practice “assumption archaeology” by digging into the hidden beliefs behind your decisions

🔹 Install Reverse Mentoring

  • • Pair with less-tenured colleagues who think differently
  • • Permit them to call out when you default to “we’ve always done it this way”
  • • Tie your own growth goals to their feedback

🔹 Codify Learning Loops

  • • Keep a live “assumption register” and update probabilities as conditions change
  • • End meetings with the question: “What would disconfirm this?”
  • • Celebrate when new information forces you to pivot


The leadership distinction:

Your strategic value isn’t applying yesterday’s playbook—it’s balancing experience with openness. The leaders who thrive in disruption are those who treat experience as context, not constraint.

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This is powerful and seeing it in the mortgage space. Be curious. Innovate. Collaborate. New ideas and fresh perspectives can drive change

I implemented reverse mentoring last quarter after reading about it elsewhere, but your point about permitting them to call out defaults makes me realize I wasn't actually listening when they did challenge my thinking. I was nodding politely while internally dismissing their perspective as "inexperienced." The framing about experience as both asset and constraint helps me see why I need to actually act on their feedback rather than just collect it to feel innovative.

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Wonder if age is a factor or just years in the same industry?

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