Why Org That Really Ought To Is The Strategy Most Founders Ignore

Why Org That Really Ought To Is The Strategy Most Founders Ignore

Most companies are built on a lie. We pretend that if we just hire "smart people" and give them a laptop, magic happens. It doesn't. What usually happens is a slow-motion car crash of miscommunication, ego, and redundant Slack channels. This is where org that really ought to comes into play—not as some HR buzzword, but as the literal skeletal structure of a business that actually scales without breaking its employees' spirits.

Honestly? Most organizational structures are accidental. They’re a series of panicked reactions to growth. You hire a VP because you're overwhelmed, they hire three directors because they're overwhelmed, and suddenly you have a "management layer" that does nothing but attend meetings about other meetings.

The Messy Reality of Structure

When we talk about an org that really ought to function effectively, we’re looking at the delta between how a company claims it works and how work actually gets done. Look at Valve, the gaming giant. They famously had a "flat" structure where desks had wheels so people could move to projects they liked. It sounds like chaos. It was. But it was intentional chaos.

Contrast that with a legacy bank. If you want to change a button color on a website, you need fifteen signatures. That’s an organization that "ought to" be stable but ends up being stagnant. The sweet spot isn't in the middle; it's in the clarity of ownership.

Success isn't about the chart. It's about the plumbing.

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What Everyone Gets Wrong About Hierarchy

People hate hierarchy because they think it's about power. It’s not. Or at least, it shouldn't be. In a high-performing org that really ought to lead its industry, hierarchy is actually about the distribution of stress.

A CEO shouldn't be deciding what font goes on the Instagram ad. If they are, the organization is failing. That’s a "micromanagement loop." According to research by Dr. Elliott Jaques on Requisite Organization, people have different "time horizons." A frontline worker thinks in days. A manager thinks in months. A CEO thinks in years or decades. When these horizons overlap or get squished, the company feels like it’s vibrating itself to pieces.

I’ve seen it a hundred times. A startup hits 50 people and suddenly everything feels slow. Why? Because the founder is still the bottleneck. They haven't built an org that really ought to operate independently of their daily whims.

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The Three Pillars of Functional Design

  1. Information Flow. If a junior designer knows a project is going to fail but can't tell the VP without a "process," you're dead. Information needs to move faster than the problems it's trying to solve.
  2. Decision Rights. Who actually makes the call? If "everyone is a stakeholder," then nobody is responsible. It’s better to have one person make a 70% correct decision quickly than a committee make a 90% correct decision in three months.
  3. The "Why" Alignment. This sounds fluffy. It's not. If your team doesn't know the North Star, they will optimize for their own departments. Sales will sell features that don't exist, and Engineering will build things nobody asked for.

Why Complexity Is The Silent Killer

Complexity is the default state of any growing system. Entropy is real. If you don't actively fight to keep your org that really ought to stay lean, it will bloat.

Think about the "Two-Pizza Rule" popularized by Jeff Bezos at Amazon. If you can't feed a team with two pizzas, the team is too big. Why? Because the number of communication lines increases exponentially with every person added. Formulaically, it’s $n(n-1)/2$. A team of 5 has 10 lines of communication. A team of 10 has 45. You can't manage 45 relationships and get actual work done at the same time. You just can't.

The Problem With "Agile" Everything

We’ve fetishized certain frameworks. We think if we do "stand-ups" and use "sprints," we’re modern. But an org that really ought to be agile is often just hiding its lack of direction behind a wall of Post-it notes. Real agility is the ability to pivot resources without a three-month re-org.

Netflix is a great example of this. Their "Culture Memo" isn't just a PDF; it's an operating manual. They focus on "Context, not Control." They give high-performers the context they need and then get out of the way. If you have to control your employees, you’ve either hired the wrong people or your org that really ought to provide clarity is failing them.

Real World Failure: The Case of "Invisible Work"

In many companies, there’s a massive amount of "shadow work." This is the work people do to bypass the official structure just to get their jobs done. It’s the "favor" you ask a friend in IT because the official ticket system takes three weeks.

If your company relies on shadow work, your formal structure is a lie. An org that really ought to support its staff shouldn't require them to act like secret agents just to ship a product. This creates massive burnout. People don't quit jobs; they quit the friction of trying to do their jobs.

Rebuilding From The Ground Up

You don't need a consultant to tell you your structure is broken. You can feel it. It feels like wading through molasses.

To fix it, you have to be ruthless. You have to look at every meeting, every approval layer, and every "dotted line" reporting relationship and ask: "Does this actually help us ship faster or better?" Usually, the answer is no. It helps someone feel "in the loop," which is a polite way of saying they’re nosy and slowing things down.

The org that really ought to exist is one where the distance between an idea and its execution is as short as humanly possible.

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Actionable Steps for Radical Restructuring

Don't do a "Big Bang" re-org. They almost always fail and leave everyone confused and terrified for their jobs. Instead, try these surgical moves.

  • Audit the Calendar. Look at any recurring meeting with more than 8 people. If no decisions are being made there, kill it immediately. Replace it with an asynchronous memo.
  • Define "Single Threaded" Owners. For every major project, there should be one name. Not a department. A name. This person has the final say and the final accountability.
  • Flatten the Communication, Not the Hierarchy. You can have a clear chain of command while still allowing anyone to talk to anyone. Encourage "skip-level" meetings where leaders talk to the front line to hear the unvarnished truth.
  • The "Rule of Three." If a process requires more than three steps of approval, it’s probably broken. Find a way to automate it or trust the person at the start of the chain.
  • Kill the "Dotted Line." Matrix organizations—where you report to a functional manager and a project manager—are often recipes for cognitive dissonance. Try to give people one clear boss whenever possible.

Ultimately, the org that really ought to be your goal is one that serves the customer, not the internal politics of the office. If your structure makes it harder to help the person paying the bills, burn the chart and start over. Efficiency isn't a luxury; in a competitive market, it's the only way to survive.