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Issue #008

The Meeting That Almost Ended My Career

I walked into what I thought was a routine team meeting.

Twenty minutes later, I was questioning everything I thought I knew about leadership.

It was my second year at Oracle, and I was leading a global sales team through a major product transition. The kind of change that makes everyone nervous, new technology, new processes, new everything.

I had prepared extensively. Slide deck perfected. Talking points rehearsed. I was ready to inspire confidence and rally the troops.

Instead, I got blindsided.

When Leadership Goes Sideways

The meeting started normally enough. I began walking through our Q3 strategy when Sarah, one of my most experienced reps, interrupted.

"Lilah, can I be honest? This isn't working."

The room went dead silent.

"The new system is a disaster. Half the team is talking about updating their résumés. And frankly, we're starting to wonder if you really understand what we're dealing with out here."

My face went hot. My carefully planned presentation suddenly felt completely irrelevant. And worst of all, I could see heads nodding around the room in agreement.

I had two choices in that moment: defend my position or face the truth.

Everything in me wanted to push back, to explain why they were wrong, to reassert my authority. But something stopped me.

Instead, I closed my laptop.

"Tell me more," I said.

The Leadership Moment That Changes Everything

What happened next taught me more about leadership than any MBA course ever could.

For the next hour, my team poured out everything, their frustrations, their fears, their suggestions I had never heard because they didn't feel safe sharing them.

I learned that the "seamless" transition I thought I was managing was actually creating chaos on the front lines. That decisions being made in conference rooms were impossible to execute in the field. That my team felt unheard and unsupported.

I had been so focused on managing up and looking good to executives that I had lost touch with the people I was supposed to be leading.

It was humbling. It was uncomfortable. And it was exactly what I needed to hear.

What Activated Leaders Do Differently

Here's what I discovered: Activated leaders don't avoid failure, they mine it for wisdom.

When something goes wrong, most leaders go into damage control mode. They deflect, defend, or disappear. But activated leaders do something different. They practice what I call "failure forensics."

They get curious instead of defensive. They ask better questions instead of giving better excuses. They see breakdown as breakthrough trying to happen.

That day, instead of trying to save face, I used the meeting as a diagnostic tool. I turned my team into my consultants and my failure into our roadmap for success.

The Forensics Process

Within a week, we had implemented three major changes based on what came out of that meeting:

  1. Daily stand-ups where field challenges were surfaced immediately instead of festering for weeks

  2. Reverse mentoring where senior reps coached me on real-world implementation challenges

  3. Decision veto power for the front-line team when new processes would create customer problems

The result? We not only hit our Q3 numbers, we exceeded them by 23%. More importantly, we built the kind of trust and communication that made our team nearly unstoppable for the next two years.

But here's the thing: none of that would have happened if I had defended my ego instead of embracing the feedback.

The Power Hidden in Your Failures

Every leader reading this has a moment like this in their recent past. A project that didn't go as planned. A team meeting that went sideways. A decision that didn't work out.

Most leaders try to forget these moments as quickly as possible. But activated leaders do the opposite, they study them like a master class.

Because here's what I've learned after coaching hundreds of executives: Your biggest breakthrough is usually hiding inside your most recent breakdown.

The failure that's embarrassing you right now? The situation that's keeping you up at night? That's not evidence that you're not cut out for leadership. That's your curriculum for becoming the leader your team actually needs.

Your Failure Forensics Assignment

I want you to think about your most recent leadership setback. Not the one from five years ago that you've already processed, the fresh one that still stings a little.

Now ask yourself these questions:

  • What was I trying to protect by handling it the way I did?

  • What information was I missing that my team could have provided?

  • If I could do it over, what would I ask instead of what would I say?

  • What is this failure trying to teach me about the leader I need to become?

Don't just think about these questions, write down your answers. The act of writing forces clarity that thinking alone can't provide.

The Next Level of Leadership

Here's what separates good leaders from activated leaders: Good leaders try to avoid failure. Activated leaders turn failure into fuel.

They understand that leadership isn't about being perfect, it's about being honest, adaptable, and committed to continuous growth.

If you're ready to transform your approach to leadership challenges, to turn your setbacks into comebacks, and to build the kind of teams that can navigate any change, I'd love to help you get there.

Ready to become an Activated Leader?

Keep leading with courage,

P.S. The meeting that almost broke me ended up being the making of me as a leader. What's your version of that meeting? Reply and tell me about a recent leadership challenge you're working through. I personally read and respond to every email.

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