I'm not even old.
They seem to have intentionally followed this design pattern, as hidden buttons often appear on hover next to adjacent buttons. I can't imagine how touchscreen laptop users feel using Asana. I won't even go into how their calendar view hides weekends, and how our team spent minutes finding the button to show weekends during a meeting.
As a digital immigrant that hasn't jumped on touch devices, I have noticed there is a shift to more "implicit" interfaces with touch devices. Not much screen space to show things, so don't waste it on menus until they are needed. I suspect that touchscreen using digital natives don't have too much of an issue with this, but I've also never used Asana.
FYI, any task that ends in `:` becomes a header. I find this easier than pressing the hidden button.
I remember it got me so frustrated I spent the rest of the afternoon writing about my "onboarding" experience:
http://lumakey.net/blog/why-i-gave-up-on-asana-after-15-minu...
That's why a lot of JIRA to Asana comparisons don't really hold up. The problem arises when a small team that needs a quick and simple to-do list start using JIRA and then compare it to other solutions which do probably 1/100th of what JIRA does. If you don't need the cruft that JIRA comes with, then that's fine...but there are genuinely orgs that do need it.
Now I'm no fan of JIRA. I don't really love it, and I fall under the camp that tolerates it. However, even then I can appreciate it for what it is and what it means to do. They can do better of course...but we can't simply compare directly between something like JIRA and Asana.