Why Enterprise Software Sucks

Rather, they are stuck with it. And deal with it, limiting the contact surface, until they cannot bear it anymore, and spend more to upgrade/get some consulting to have the solution reorganized for them.

On one hand, you have purchase departments that are not the target users, and decide only based on paper reports, what to purchase. Losing the run from the start line. That's a given.

On the other hand, you have those who prefer to outsource the understanding of their own workflow/tooling/business, that could leave them somehow unique and different, to some outside flexible product that claims to solve that (and that meets this and this requirement from that body & that set of laws), but still requires armies of consultants to make it work properly, although it does not cover really your use case, so you better adapt your way of work to what "they" say is good (got Agile anyone?).

Why? Because regulations. Because market/business standards. Financial due diligences.

And why would they not prefer that? They (anyone, we) do not care. We are not paid to care for that. Or rather, we get rapidly burnt for caring.

That's like the entropy law for software & processes in enterprise in general.

Oracle, for instance (but that's valid for so many, if not all, enterprise-targeted solutions), didn't sell itself based on technical merits, you know.

Business are complicated, yes. And they get even more complicated because of people lacking of the courage to say fuck you to the salesman.

The spreadsheet jockey who just likes doing cool things with the data. Excel is just powerful enough to satiate this guy long enough for him to fall out of the habit of rethinking his workflow. If he had moved on earlier he'd be a DBA or a data scientist by now.

The other type is the small business owner who is pretty good at spreadsheets but whose business is outpacing his spreadsheets' ability to keep up.

On three separate occasions I've had this sort try to hire me to help find ways to make their workflow scalable, perhaps by helping them write a little custom software. The problem is usually that the time for finding an alternate method was years ago. The spreadsheets these people come up with are amazing, it's like they've tricked out their tricycle so much over the years that it can now fly, just not well.

They always want to pay for my spare time, but the complexity is always such that they need somebody full time.

In terms of decision makers vs. users, the issue is that there is more than one group of users. For Blackboard, there are faculty, students, and administrators. There's a venn diagram of overlapping desires there, but there's also plenty of room for contradictory requirements.

Second is the nature of enterprise software:

--It's large, expensive to buy and expensive to maintain. So, you can't go switching it out every time a cool new product comes to market with new convenient features. You're stuck with it.

--But the vendor doesn't want to lose customers, so they figure out a way to bolt on the most popular things that come along, usually 2-3 years afterwards.

--The implementation is clunky and awkward and adds complexity for users that don't need the feature and maintenance of the system

The alternatives aren't great either: Pick an up & comer, like Canvas. It's smoother, more refined UI, less bloat, etc. People switch, because it does 80% of what they need very well, and they decide they can live without the 20% hardly anyone ever used. But over time, Canvas gets caught in the same trap. Users clamor for more features over time. They bolt on more and more, and the process repeats.

Sometimes a corporation (or university) will try to circumvent this. They go "best of breed" for all functionality

--They buy a minimalist LMS, they buy a separate system for advising & appointments etc., they buy a third system to replace the financial component handled by Blackboard Transact, etc.

--And, for a short period of time, users may be a little happier, until bolt-ons creep into each product, but maintenance & integration costs explode on the infrastructure side.

--If it gets too bad, someone in leadership will eventually say, "Why are we spending 3x as much on license maintenance with full time employees to keep it all running when we can get one single system to do it all for us?

And some variation of the above cycles repeat over & over.

I worked on a product recently where we built a new stripped down mobile version of our enterprise software that was extremely easy to use for the average user, but had minimal functionality for management. Our manager users have never been big adopters of our mobile software, because they spend most of their time looking at large reports that don't work well on mobile, so we figured this was a safe strategy, at least for the initial launch.

However, we saw extremely low adoption, because managers would try the app, see that the minimal amount of features for them, and then they wouldn't recommend it for the rest of our users. We refocused to adding features for management, and we started to see much larger adoption by the average user.

Selling user focused software to the someone who isn't the main user will always be an uphill battle. The companies that have had the most success are those like Slack that are able to get into the organization without the buyers approval first.