Conclusion
The hard part about legacy modernization is the system around the system. The organization, its communication structures, its politics, and its incentives are all intertwined with the technical product in such a way that to move the product, you must do it by turning the gears of this other, complex, undocumented system.
Part of the reason legacy modernizations fail so often is that human beings are incentivized to mute or otherwise remove feedback loops that establish accountability. We are often unable to stop this because we insist on talking about that problem as a moral failing instead of an unconscious bias. Engineering organizations that maintain a separation between operations and development, for example, inevitably find ...
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