John Cutler · 6 min read · Product Teams
AI Won’t Save the Kingdoms We Built
Read the original on cutlefish.substack.com →
AI won’t save the kingdoms we built; the piece argues that the real work is reforming the fiefdom‑driven org design rather than outsourcing problems to AI. It explains how autonomy, accountability, and scale created tangled dependencies and hard-to-manage end-to-end experiences, and asks whether AI can improve outcomes without addressing the underlying structure and shared responsibility.
Key Takeaways
- Fiefdoms were built on autonomy and accountability assumptions that created silos and coordination pain.
- As organizations grow, dependencies and blast radii increase, making end-to-end experiences hard to reason about.
- The expansion of 'products' and sub-orgs in the ZIRP era masked real work and added fragmentation.
- AI could help, but only if we reform the underlying structure and embrace shared responsibility across teams.
Excerpt
This post is about the people who built the fiefdoms now looking to AI to save them from the fiefdoms, and why that will only work if we are honest about what those fiefdoms were built to avoid in the first place. Unfiltered Saturday morning coffee writing engaged. The people who built the fiefdoms are now complaining about the fiefdoms That is the part I can’t stop thinking about. Some of the same people who benefited from riding the ZIRP wave to safer places of leadership are now waxing, not very poetically, about flattening orgs, 10x engineers, getting into the…