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Leading Together

Why do Smart Leaders Keep Solving the Wrong Problems

Published about 1 month ago • 3 min read

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Hi Reader,

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Most leadership teams are working hard. They’re engaged, responsive, and constantly solving problems. But despite all that effort, persistent issues continue to linger, making it hard to break through to the next level or build a workplace people genuinely love being part of.

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It’s not for lack of trying. Leaders are addressing challenges, filling gaps, putting out fires. But still…culture feels off. Collaboration breaks down. Momentum stalls.

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If this sounds familiar, the core issue might not be your people. It could be the systems they’re working in.

People vs. Systems

When someone isn’t meeting expectations...
When cross-team collaboration keeps breaking down...
When the culture feels off, or momentum slows down…

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It’s tempting to assume the issue is about individual performance.

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In At the Heart of Work we frame it this way:

“Systems shape behavior more than we realize, and far more than most teams account for.”

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What looks like a motivation issue is often a role clarity issue. What feels like a leadership gap might actually be a poorly designed meeting rhythm or accountability gap. And what gets labeled a “performance problem” is sometimes just the result of a broken process.

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Your Hidden Operating System

Every organization runs on a hidden structure. We simply call it their Organizational Operating System (Org OS).

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It’s not just your org chart or strategy deck. It’s the underlying structures, habits, and expectations, often undocumented, that shape how work actually gets done.

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Most teams didn’t design their Org OS. They inherited it. When it goes unexamined, it drifts into default, shaped by old decisions, blurred roles, and vague norms.

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An Org OS running on default for too long can have a significant negative impact.

  • The meeting everyone dreads
  • The decision that never gets made.
  • The tension between key team members that just won’t go away.

These aren’t random frustrations, they’re signals. They point to an operating system that’s been inherited, not intentionally built. The turning point comes when you stop treating these issues as one-offs and start asking what’s going on beneath the surface.

Enter the Upstream Mindset

Embracing an Upstream Mindset is a way of looking beyond symptoms to understand what’s creating them in the first place.

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“What’s underneath the surface is almost always more influential than what’s visible on top, and yet we rarely make time to investigate it.” Ch. 1 - At the Heart of Work

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This mindset shift allows leaders to stop spinning in the same challenges and start seeing what’s actually causing them. It turns reactive problem-solving into thoughtful system redesign.
It’s how high-performing teams begin to work with intention, rather than continuing to accept the default systems they’ve been working in, often for years.

Join Our June 18th Workshop: Why do Smart Leaders Keep Solving the Wrong Problems?

If this resonates, don’t miss our upcoming session on June 18th.

This 60-minute, interactive workshop explores the invisible system shaping your team’s behavior and equips you to see and solve problems differently.

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What you'll learn:

  • Reframe the Challenge: Why leaders often default to blaming people, and how to shift your approach.
  • Harness Your Org OS: How to identify and influence your team’s hidden operating system.
  • Sharpen Your Skills: Practice applying an upstream mindset to real challenges and design better solutions.

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We hope to see you there.

-Shaun and Joe

Get the 6 Levers Book

In today's fast-paced business environment, creating a healthy and high-performing organization is more challenging than ever. That's where At the Heart of Work comes in - a practical guide that introduces the 6 Levers Framework, designed to help leaders like you align people and systems effectively.

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Whether you're leading a small team or an entire organization, the insights from this book will equip you to build a resilient, purpose-driven workplace where teams thrive.

Upcoming Events & Opportunities:

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Leading Together

with 6 Levers

Leading Together is for senior leadership teams who want to become more cohesive and high performing. In each newsletter, 6 Levers co-founders Shaun Lee and Joe Olwig break down real-world case studies and share insights from their work with executive teams across industries. You’ll hear the patterns behind what makes leadership teams thrive—and what holds them back. Most importantly, every newsletter shares practical applications you can apply with your team.

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