Episode
· 03:12
🎙️🔍 Podcast Summary of TBM 347: “Why Don’t Our Leaders Care About How We Work?” by John Cutler
Why does intentional company design feel like a niche obsession instead of common practice? In this thoughtful piece, John Cutler dissects the frustrating disconnect between leaders, managers, and the people who care deeply about how work actually gets done. He argues that designing a great organizational operating system (OS) isn’t just a process problem—it’s a matter of skill, awareness, priorities, and power dynamics. Many leaders, even brilliant ones, are simply not wired—or incentivized—to care about structure and workflow unless it directly benefits them. Meanwhile, those who do care often lack authority or are buried under the weight of day-to-day execution. Cutler doesn’t just complain—he offers concrete insight into why this dynamic persists and what change-makers inside organizations can actually do about it. As he puts it, “You can go a long way in keeping your own private document of how things work… sometimes, the big blocker was someone taking the stubborn time to shine the mirror back on the company.”
🔑 Key Points:
Most leadership teams aren’t thinking deeply about how work happens—they’re too busy chasing goals and managing up. Thoughtful design of how people work is rare unless it’s championed from the top.
Design clarity falls into a gray area between “leadership,” “management,” and “process design”—and because it doesn’t fit neatly into any category, it’s often not discussed at all.
Just because someone is a strong operator or leader doesn’t mean they know how to create scalable systems—OS design is a distinct skill that many overlook or devalue.
"You imagine that when you get into the room with these people, you'll suddenly be exposed to super thoughtful discussions… but it isn't like that at all," Cutler quotes a tech exec—shattering the illusion of strategic introspection at the top.
Founders are hit-or-miss when it comes to operating system nerdery. Some love it, some avoid it entirely. Their interest level often dictates how intentional a company's work environment is.
Mid-level pushes for consistency often fail because they threaten team autonomy and are dismissed as unimportant “process talk”—creating a clash between global efficiency and local independence.
Many executives see process as beneath their pay grade; they offload it to Chiefs of Staff, Product Ops, or Program Managers—who may not have the deep experience needed to treat the root issues.
Much of a company’s true “OS” is created reactively, in wartime mode, and then frozen—leading to “Zombie Processes” that no one quite questions but everyone continues following.
🧩 Practical Takeaways and Recommendations:
If you care about this stuff, test the waters—leaders may be intentional in their heads but not explicit on paper. Begin with behavior-focused conversations like, “What are we trying to encourage or discourage?”
Leaders won’t engage with theory—ground your feedback in specific, relatable stories of how decisions and work happen in reality.
Partner up with Chiefs of Staff and Ops roles where possible—they might be overwhelmed and glad for your clarity and support.
You may need to “be the mirror”—quietly document how things actually work and share that back with your team or leadership when the timing is right.
Don’t expect people to change unless they see tangible improvements. Most are skeptical by default and too underwater to strategize.
🎧 Listener Challenge:
If you’re frustrated with how your company works, don’t just vent. Take one meeting, one team ritual, or one slack conversation—and experiment with improving it. Start tiny, stay curious, and see if others notice.
đź“š Related Resources:
That’s it for this summary of TBM 347. Until next time, keep doing the slow, intentional work—someone has to! 💼🧠🎙️
Link to Article
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