The Inverse Conway's Law

When Organizations Become Their Software

Melvin Conway famously observed that software systems tend to mirror the communication structures of the organizations that create them. But have you noticed the reverse?

Organizations are increasingly reflecting the software they’ve built.

Take a look at how development organizations in global enterprises are structured. Large-scale agile frameworks like SAFe organize teams around legacy SaaS monoliths, embedding rigid workflows and siloed teams into the company’s DNA. These structures, originally meant to streamline development, now shape how companies think, move, and make decisions. And in the age of AI, that’s a problem.

The Challenge

AI paradigms require flexibility, cross-functional collaboration, and rapid experimentation. Yet many organizations are shackled by software architectures designed for an era of stability, not agility. Instead of accelerating transformation, these outdated structures resist it. The very systems built to support operations end up defining them, limiting adaptability just when AI demands the opposite.

So how do we break free? How can organizations reclaim their ability to evolve without being constrained by legacy software structures?

Breaking the Pattern

Here are four ways to ensure your organization evolves beyond the constraints of its software and can start to leverage AI effectively:

1️⃣ Embrace Modular Systems

Replace monolithic software with composable architectures that mirror the fluidity AI demands. Think microservices, orchestration layers, and APIs that enable quick adjustments. The goal isn’t just better software—it’s building a foundation for adaptability.

2️⃣ Rethink Processes, Not Just Tools

AI isn’t just another layer in the tech stack—it demands reimagining workflows and decision-making. Break down silos and empower teams with data-driven autonomy. The organizations that thrive in the AI era will be those that treat AI as a core design principle, not a bolt-on feature.

3️⃣ Foster a Learning Culture

Encourage teams to experiment, iterate, and fail forward. AI thrives in environments where curiosity and adaptability are the norm. Make room for exploration, and don’t let rigid structures kill innovation before it starts.

4️⃣ Support the Troublemakers

There is already passion and experience within your teams. Find those who haven’t resigned to the status quo—those who question, push, and challenge assumptions. Task them with small, quick-change programs that create momentum for larger transformation.

A New Era of Design

In the age of AI, organizations must shape software, not the other way around. By aligning systems with people-first principles and emerging AI capabilities, we can lead innovation rather than chase it.

The question is no longer whether AI will change how we work—it already is. The real question is: Will your organization be defined by its software, or will it design the software that defines it?