7 Brutal Self-Awareness Questions Every Leader Needs to Answer (Part I)

  1. When you’re absent from the office, does productivity and decision-making continue at the same pace or does everything slow down?
  2. When was the last time someone on your team respectfully disagreed with you in a meeting?
  3. Do people tend to come to you with solutions or just problems, and what might that reveal about the culture you’ve created?
  4. How often do you find yourself being the one with all the solutions versus facilitating others to problem-solve?
  5. Do your direct reports tend to wait for your opinion before sharing theirs?
  6. When projects fail or fall short, do team members primarily blame external factors or take personal responsibility?
  7. If your team members were completely honest about your leadership behind closed doors, what would surprise you most? What three words would they use to describe your leadership style—would those align with how you see yourself?

Meet Sam.

Father. Good husband. Volunteer coach for his son’s basketball team. Works hard—most days, one of the first in the office and last to leave. Worked his way through college. Now he’s a Senior VP of Corporate Affairs at a financial institution, been there five years, leads a team of six direct reports.

Here’s what nobody’s telling Sam: he’s a terrible leader.

He doesn’t hold people accountable. His expectations are unclear. He tries to do everything himself. People around him, peers, leaders above him, even his direct reports, see the wreckage. But no one is speaking up.

And Sam? Sam has no idea.

But here’s what haunts me: Why can’t he see it? How does a capable, hardworking, well-intentioned person become so disconnected from their impact? What creates this huge gap between intention and reality?

I’ve been thinking about this because I keep running into versions of Sam:

The executive director of a nonprofit with a board in total chaos. Everyone knows engagement has collapsed, but she’s paralyzed, unable to address it. And according to her, it’s everyone else’s fault, but hers.

The senior pastor of a church who recently had a health crisis. When he was out, everything came to a grinding halt. ground to a halt. Not because the church couldn’t function without him, but because he’d built a system that required him to be the solution to every problem.

The “big-time” executive whose numbers, awards, and board seats are all impressive. The truth? Employees quietly suffer under leadership that confuses activity with impact.

Same pattern. Different settings. And always the same question: How do smart, decent people become so dangerously unaware?

The truth is, holding a mirror up to ourselves takes courage.  Sam isn’t a villain; he’s a dedicated leader who suffers from lack of self-awareness. In Part II (next newsletter), we’ll unpack the underlying psychology of why these blind spots exist, why your team is likely staying silent, and how to transition from being the “indispensable problem-solver” to a truly effective leader.

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