I work in the UX space. My team presents new designs and features to customers before building them. We actually sit 1 on 1 with a customer and show them mockups and such of some future idea for the product. One of the questions asked to customers is something to the effect of, "Looking at design A, would you say it looks more or less 'modern' than design B?" This is usually the justification higher ups use for making these changes. I'm not saying this is a good way of product direction (do customers really know what they want?) but this is usually how the justification happens.

Play safe, if you come up with a wacky logo and it fails then your reputation suffers.

Generally there is design language for every decade or more. Not following this unless it is sufficiently old or well established just looks dated in a wrong way.