Why your leadership growth is stuck (and how to break free)

THE ART & SCIENCE OF LEADING SELF
Beyond Surface Changes

My friend, in last week's newsletter, we explored the Observer-Action-Results (O-A-R) framework and how your perspective shapes your outcomes. Today, I want to dive deeper into something I briefly touched on: the profound distinction between First Order and Second Order Learning.

Picture this: You've decided to improve your leadership communication. You read books, attend workshops, and diligently practice new techniques. Yet somehow, your team still seems hesitant to bring you bad news. Your direct reports still hedge their responses in meetings. Sound familiar?

You're experiencing the limits of First Order Learning. 🤔 

First Order Learning: The Comfort Zone That Holds You Back 😱

First Order Learning is like changing the toppings on your pizza while keeping the same base – you're modifying actions without examining the foundation. It's comfortable. It's familiar. And it's precisely why so many leadership development efforts fall short.

When you engage in First Order Learning, you:

• Focus on new actions and behaviors

• Keep your fundamental assumptions intact

• Stay within familiar thought patterns

• Seek solutions that don't challenge your core beliefs

Here's the truth: First Order Learning feels productive because you're doing something. But it's a bit like rearranging deck chairs on the Titanic – lots of action, minimal impact.

The Transformative Power of Second Order Learning 🦋

Second Order Learning is different. It's not about changing what you do – it's about transforming how you observe and interpret the world. It's examining the pizza base itself, questioning whether pizza is even what you need.

Let me share a story about Casey*, a client who struggled with delegation. This client’s First Order Learning approach involved:

• Creating better task lists

• Setting up more structured check-ins

• Developing detailed progress tracking systems

Yet his team still felt micromanaged. Why? Because he hadn't examined his deeper assumptions about trust, control, and leadership.

When Casey shifted to Second Order Learning, he started asking different questions:

• "What beliefs do I hold about my role as a leader?"

• "How do my experiences with failure shape my need for control?"

• "What am I afraid might happen if I truly let go?"

This deeper inquiry revealed something profound: His resistance to delegation wasn't about processes or systems – it was about his identity as a leader. His self-worth was tied to being the person with all the answers.

*Client name changed to maintain privacy.

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FROM INSIGHT TO ACTION
Why Second Order Learning Feels Hard (But Is Worth It) 💪🏽

Second Order Learning is challenging because it requires you to:

1. Sit with uncertainty

2. Question long-held beliefs

3. Face uncomfortable truths about yourself

4. Challenge your identity

Most leaders avoid this depth of inquiry because it feels vulnerable. It's easier to download another productivity app or learn a new communication technique than to examine your fundamental beliefs about productivity or communication.

But here's what makes Second Order Learning transformative:

• It changes how you see, not just what you do

• It addresses root causes, not symptoms

• It creates sustainable transformation, not temporary changes

• It impacts all areas of your leadership, not just specific behaviors

O-A-R Meets Second Order Learning 🔋

Remember our discussion of the Observer-Action-Results framework? Let's connect these dots to reveal what's possible when you embrace Second Order Learning.

As an Observer engaging in First Order Learning, you might notice your team's low engagement and immediately jump to solutions: better perks, clearer goals, more recognition. These actions might create temporary spikes in motivation, but they don't address the deeper patterns at play.

But what happens when you apply Second Order Learning to your role as Observer? Everything shifts.

Here's what becomes possible:

In Your Self-Leadership:

• You start recognizing patterns in your leadership triggers before they hijack your responses

• Your decision-making becomes more nuanced as you notice the assumptions influencing your choices

• You develop greater emotional agility, moving from reactive to responsive leadership

• Your resilience deepens because challenges become opportunities for learning rather than threats to your identity

I saw this transformation with a CEO client who initially approached every challenge as a problem to solve. Through Second Order Learning, she began to see challenges as mirrors reflecting her own leadership assumptions. This shift didn't just change her actions – it transformed her entire leadership presence.

In Leading Others:

• Your team begins to mirror your deeper reflection, creating a culture of thoughtful inquiry

• Conflicts become opportunities for examining collective assumptions rather than battles to win

• Innovation flourishes because people feel safe questioning established ways of thinking

• Your influence grows as others recognize and trust your commitment to genuine understanding

Think about it: When you're operating from Second Order Learning, you're not just changing what you do – you're evolving who you are as a leader. This evolution ripples out, touching every aspect of your leadership ecosystem.

The best part? This transformation is available to you right now. It starts with a simple choice: Will you settle for changing actions, or are you ready to examine the observer you've become?

FROM INSIGHT TO ACTION
Putting It Into Practice

Here's a simple but powerful practice to begin developing your Second Order Learning capacity. I call it the "Question Behind the Question" exercise:

1. When you face a leadership challenge, write down your immediate solution.

2. Ask yourself: "What assumption is this solution based on?"

3. Then ask: "Why do I hold this assumption?"

4. Finally: "What might be possible if this assumption weren't true?"

For example:

• Challenge: "My team isn't innovative enough"

• Immediate solution: "We need more brainstorming sessions"

• Question 1: "What assumption is this based on?"

  • "Innovation comes from formal processes"

• Question 2: "Why do I believe this?"

  • "Because that's how I learned to drive innovation"

• Question 3: "What if this weren't true?"

  • New possibilities emerge about psychological safety, creative freedom, etc.

Do this exercise daily, even with small challenges. The goal isn't to invalidate your first solutions but to develop the muscle of looking deeper.

Remember, my friend, transformation isn't just about doing different things – it's about becoming a different observer of your reality. Second Order Learning isn't just a technique; it's a gateway to fundamental change.

The butterfly doesn't just adjust its caterpillar strategies – it transforms entirely. 🦋 Your leadership journey invites the same level of metamorphosis.

EXCELLENCE UNBOUNDED
How I Can Help You

🚀 CEO Coaching Programs: Are you a CEO who wants to:

• Skillfully navigate uncertainty 

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• Drive results

Developing greater leadership capacity in 4 key domains (Mindset, Courage, Resilience, & Innovation) will empower you to do all three.

Book time to learn about the bespoke 1:1 coaching programs I deliver. During this call, we will talk about your challenges, your goals, and how we might partner to fully “unbound your excellence.”

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A few past clients include KraftHeinz, Amazon Women @ Payments, PAHEi, & the Panamá Chapter of the International Coaching Federation (I delivered this talk in Spanish).

If you are interested in having me speak at your event, please fill out this form.

Until next Sunday,

Shawnette