A lot of little pet projects- many of which flounder about wasting resources and never coming to fruition. Frustrating to see resources wasted on things that-- even if they do get completed-- the customers really don't want as much as leadership/management thinks they do.
Moreover, there is a large disconnect between leadership/management and our user base. Leadership/management is out of touch with our main product (Designer) and the niche value it provides. For example, having seen many years of quarterly innovation days, leadership/management does not contribute/participate. (Participation, otherwise, is usually very high across the company-- even outside of the engineering org.)
When the company wants to update/modernize a product line (e.g., server), the tendency has always been to rewrite all functionality from scratch. With decades-old legacy products and a bunch of rosy-eyed (usually newly-hired) developers, this leads to a lot of reinventing the wheel (in the best case) and a lot of new problems (in the worst case). This has happened time and time again with various iterations of lightweight, web-based versions of both the desktop and server products. Every time, there is a naivete (or perhaps hubris) that THIS rewrite will avoid all of the problems from the previous rewrites; more often, there are just new defects and anomalies being introduced (not all of which are being identified).
In response to diverging visions, there seems to be a tendency to terminate many passionate advocates for the main product (including the original CTO, who wrote this product himself). This has led to displaced/disjointed excitement for the product and an overall decrease in morale across (at least) the engineering org.