You nailed it. Their UI and UX are both just really bad but it's a kind of hidden complexity that sneaks up on you and you don't realize it until you actually start using the product. They also had a horrible (like, really....really bad) mobile app for the longest time and even their new one uses very very weird UX paradigms for no clear reason.
My favorite example of their strange UI/UX pattern is trying to make a new task header in list mode. There isn't a dedicated button for this — or is there?! Try to hover your pointer on "Add Task" and a new button magically appears next to it, on:hover, called "Add Section"! Just like 1999 all over again, but without the GIFs and marquees.
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.
> I can't imagine how touchscreen laptop users feel using Asana.
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.
I really don't like how you have to be connected to the internet to use the mobile app. I'm a diehard asana user, but this kills it for me when I'm on airplanes. I'm on airplanes 2x a week.
What people forget is that JIRA is a more complex product. Probably by orders of magnitude. There is SO MUCH you can do with JIRA and so many different integrations that while it's very clunky, I feel they don't get enough credit for managing all that complexity in some manner that is at last somewhat sane. In fact, clunkiness comes with that territory of complexity, there's just really no way around it (well, this is a simplifying statement, but the point is that different tradeoffs would have had to be made).
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.
I'm not even old.