The Day I Failed Admirably—And What IT Leaders Can Learn From It

Success in leadership isn’t always about delivering the perfect strategy, making the right decision, or walking out of a meeting feeling victorious. Sometimes, real leadership is about failing perfectly—and having the humility, honesty, and resilience to admit it.

Situation:

Today, I failed. Admirably.

In a recent coaching session, my coachee—an experienced Sr. manager—came in prepared but admitted he hadn’t followed through with any of the agreed-upon action items from our last session. Workload had taken over. He had improved his energy levels by exercising in the morning but hadn’t optimized his communication strategies or streamlined his workflow as planned.

On the surface, this was fine. Coaching isn’t about compliance; it’s about self-directed growth. But something about his words triggered something in me.

For a split second, I felt rejected.

Not in a dramatic way, but enough to feel a shift in my own energy. My Inner Judge (“The Blamer”) whispered: You didn’t make an impact. He ignored your advice. You failed.

And then my Hyper-Achiever (“The Trophy Seeker”) chimed in: You should have done better. You should have pushed him harder. If he isn’t executing, it means you weren’t effective enough.

For a few seconds that felt like an eternity, I was hijacked by my own thoughts.

Task:

As a CIO or IT leader, this might sound familiar.

How many times have you walked into a room with an airtight IT strategy, only to have executives ignore your insights or broke their promises to support you? How often do you feel like you’re giving clear guidance, but your team isn’t executing on it? How many times have you felt unseen, unheard, or undervalued—despite the fact that you know you bring immense value?

The default response?

• Get frustrated.
• Blame others. ("They just don’t get it.")
• Overcompensate. ("I need to push harder next time.")
• Check out. ("Why bother? They won’t listen anyway.")

But leadership isn’t about letting these emotional hijacks dictate our next move. It’s about recognizing them, regulating them, and using them as a tool for influence instead of a weapon of self-destruction.

Action:

And so, I had a choice.

I could ignore what had just happened, pretend I was unaffected, and carry on professionally. Or—I could use this moment to model something deeper: emotional intelligence in action.

I chose the latter.

Instead of masking my emotions, I consciously regulated them. I adjusted my tone. I paid attention to my body language. I shifted my energy just enough to get my coachee’s attention.

At first, he didn’t notice. But when I asked, he admitted that he had sensed something different but hadn’t inquired about it.

Why?

Because he assumed that, as a professional, I should know how to "control" myself.

That was my moment.

I asked him: What do you do when you notice someone’s energy shift? Do you ignore it, or do you lean in with curiosity?

We explored how the ability to notice, name, and navigate emotional shifts is what separates transactional managers from transformational leaders.

By the end, my coachee had a realization—not just about his leadership approach but also about his own ability to recognize and influence the emotions of those around him.

Result:

What started as my perceived failure turned into his leadership breakthrough.

And that’s the lesson: Leadership isn’t about being perfect. It’s about being present. It’s about having the courage to use every moment—especially the uncomfortable ones—as an opportunity for growth, connection, and influence.

Reflection for CIOs & IT Leaders:

• How often do you suppress your emotions in board meetings instead of using them as a tool for insight and influence?
• When was the last time you paused to notice the energy shifts in your team and explored what they might mean?
• What would change in your leadership style if you embraced “failing admirably” instead of chasing perfection?

The best IT leaders aren’t the ones who always get it right.

They’re the ones who know how to pivot when things go wrong—not just in technology, but in leadership, in influence, and in human connection.

And that? That’s a skill worth mastering.

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