My university just announced that it’s dumping Blackboard, and there was much rejoicing. Why is Blackboard universally reviled? There’s a standard story of why "enterprise software" sucks. If you’ll bear with me, I think this is best appreciated by talking about… baby clothes!
There are two types of baby outfits. The first is targeted at people buying gifts. It's irresistible on the rack. It has no fewer than 18 buttons. At least 3 people are needed to get a screaming baby into it. It's worn once, so you can send a photo to the gifter, then discarded.
Other baby outfits are meant for parents. They’re marked "Easy On, Easy Off" or some such, and they really mean it. Zippers aren't easy enough so they fasten using MAGNETS. A busy parent (i.e. a parent) can change an outfit in 5 seconds, one handed, before rushing to work.
The point is, some products are sold directly to the end user, and are forced to prioritize usability. Other products are sold to an intermediary whose concerns are typically different from the user's needs. Such products don't HAVE to end up as unusable garbage, but usually do.
OK, back to Blackboard! It’s actually designed to look extremely attractive to the administrators (not professors and definitely not students) who make purchase decisions. Since they can't easily test usability, they instead make comparisons based on… checklists of features. 🤦🏽♂️
And that's exactly what's wrong with Blackboard. It has every feature ever dreamed up. But like anything designed by a committee, the interface is incoherent and any task requires at least fifteen clicks (and that's if you even remember the correct sequence the first time).
Software companies can be breathtakingly clueless when there's a layer of indirection between them and their users. Everyone who's suffered through Blackboard will have the same reaction to this: try having less functionality! edscoop.com/how-canvas-cam… 
The grumbling about Blackboard has finally gotten loud enough that schools are paying a modicum of attention to usability when evaluating alternatives. Blackboard's market share has dropped dramatically and this will probably continue. Good.
Here’s the kicker, though. It's extremely likely that whichever vendor emerges on top will fall into the same trap. The incentives almost guarantee it. Once profs and students put down the pitchforks, committees will go back to their checklists, and feature creep will resume.
Blackboard is 20 years old. If Twitter is around in 20 years, let's see how this prediction holds up. And now I have to go rescue a three-month old from an extremely cute and equally uncomfortable outfit.
