Daniel Zacarias has some tips for How to Deal with “Sinatra” Stakeholders—those people (usually HiPPOs¹) who only want to design and build things their way. At the end he makes an important point:

These stakeholder attitudes don’t come out of the blue or from malfeasance. They result from misalignment and even when you can’t change your entire organization, you can definitely affect change around your product.

This is something I constantly have to remind myself about. If someone isn’t buying into our vision or “getting” the design, it’s not their fault. It’s ours. It is our responsibility to bring people along on the journey. We can’t blame them if they come into a project context-less and then ask difficult questions.