27/09/2024
Your stakeholder does not get you. They do not understand the materiality of the software. They have not felt the code pushing back against attempts to conform it to some new requirement. Programmers go through a tension-release cycle: first the friction of dealing with reems of legacy code, and then the dopamine hit of solving the problem. Your stakeholder is not engaged in this cycle.
Technical reasons for why something cannot be done in X amount of time do not land with your stakeholder if they make no intuitive sense to them. They do not land with them even if they say they do. If the given explanation carries no weight, your stakeholder (and their stakeholders, etc) will look for other explanations: namely foot-dragging and an unwillingness to "get things done" on your part.
This means that you should not allow technical obstacles to accommodating future requirements to accumulate in the codebase that will not make intuitive sense to your stakeholder, as this will only rebound on you.