Ralph, I think it is definitely worthwhile to have the conversation. It raises a lot of questions I would have reasonable answers to before I walked in the door like:
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why should they change their style? Does it not align to their target consumer? Does it not align to their brand values/principles?
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what would a style (or design language system, DSL) that embodies their brand principles and target user aspirations look like and why?
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Even if I could reasonably prove 1 and 2, I’d try to dig deep on if the organization would be open to that change, what it would take for it to happen, if I would have any authority to help shepherd that effort?
Otherwise you could run the risk of coming in and seeming like you want to change the look of their product without having the business rational to do so, which is a bad look for designers. Of course we have personal taste. That taste needs to be aligned to the goals of the business. When I talk to clients about this I speak about it in terms of looking for the highest common denominator instead of the lowest.