The mistake about mistakes? Everyone says they learn from mistakes, but don’t. The truth: leaders don’t have time to actually reflect. They just move to the next quarter, sprint, or fire. It’s not the catastrophic failures that hold us back—it’s the unexamined small ones. Stop failing on repeat.

Leadership Autopilot

We’re usually rewarded for momentum, not reflection. When you’re focused on “keeping moving” and that’s your mantra, you’ll keep hitting the same blind spots. The problem isn’t making mistakes; to err is human and all that. It’s not extracting from them all the learning that you could have. As a result, the same thinking errors keep repeating and replicating across the org.

Your mistakes are the missed goldmine. The subtle, non-fatal mistakes are the richest learning material. The hire who’s “okay, but not great.” The product bet that didn’t crash but never took off. The process that “kind of works” but drains morale. These are easy to ignore, but they’re where your improvement potential hides. You can’t optimize what you don’t pause to examine.

The Practice: Squeezing Failures

Let’s consider the personal mistakes you can learn from, putting aside the organization in its entirety. Set a cadence for introspection sessions, like personal retros.

Ask yourself regularly:

People

• Who did I hire in the last 3–6 months? Are they where I hoped they’d be?
• If not: was the problem in selection, onboarding, or my expectations?
• Did I give them enough clarity, feedback, and growth?
  

Performance

• Who in my team plateaued because I was too busy?
• Where have I failed to give the feedback I already know is overdue?
  

Perspective

• What did I believe three months ago that I no longer do?
• When did I change course—and what faulty assumption led me to the original choice?
  

These aren’t guilt exercises—they’re R&D for your judgment.

The Mindset Shift: From Regret to Yield

Don’t see mistakes as “past you messed up.” Start seeing them as future ROI you haven’t claimed yet. Every unexamined decision is wasted tuition. You already paid for it and might as well get the lesson. Reflection is how you turn experience into expertise.

Block 30 minutes once a month to look back at:

• Your calendar and notes (what consumed your energy)
• Your hires and team shifts
• Your major decisions and pivots
• Make it tangible: write down “What I got wrong” and “What I’d do differently.”
• Over time, you’ll build your own failure playbook—a map of your evolving judgment.
  

The best leaders don’t avoid mistakes—they metabolize them faster. Reflection isn’t slowing down—it’s building speed sustainably. If you’re not squeezing your failures, you’re leaving growth on the table. Pause this week and review one recent decision that didn’t go as expected. Extract the pattern.