A product team saved $150 million in margin improvement not by building new features, but by decommissioning a long tail of customized, on-prem legacy products. This "unsexy" work eliminated significant operational drain from support and maintenance, directly impacting the bottom line in a way new features rarely can.

To avoid decline, managers of mature 'cash cow' products must operate on two tracks. They should rapidly test solution-based iterations to optimize the existing product, while simultaneously dedicating resources to high-level problem discovery to identify the company's next source of growth.

To get executive buy-in for technical debt work, visually demonstrate how it blocks high-value future features. Present it as a choice: we can do this necessary refactor now, or we forfeit the ability to build the things that will make us money later.

In a complex legacy environment, internal motivations like improving developer experience or modernizing technology often fail to gain traction. The initiatives that successfully navigate the process are those that can clearly articulate and deliver tangible value to the end customer.

According to Experian's tech CEO, the most contentious decisions involve enforcing standards by retiring tools that developers and clients love. These migrations are costly, create friction, and require careful, consensus-driven planning to manage the human element of change.

Finance departments often push for system rewrites based on fixed 3-5 year depreciation schedules. Once software is fully amortized and has a book value of zero, accounting principles create pressure to invest in a new system to put a new asset on the books, regardless of the old system's functionality.

To successfully advocate for a working legacy system against modernization pressure, you must be deeply aligned with its profit and loss. If someone else controls the P&L, your customer-centric arguments will be overruled by financial or political motivations, making your position untenable.

Contrary to the stereotype of being 'dusty' or resistant to change, companies that last for centuries are masters of adaptation. Their longevity is direct evidence of their forward-thinking ability to navigate crises, from wars and pandemics to technological disruption.

To transition to AI, leaders must ruthlessly dismantle parts of their existing, money-making codebase that are not competitively differentiating or slow down AI development. This requires overcoming the team's justifiable pride and emotional attachment to legacy systems they built.