Maybe the above scenario is a slight exaggeration, but to work in America in the year 2024 is to drown in a sea of apps. If you want to take time off, there's an app for that. And it's different from the one where you sign up for benefits or submit expenses or handle reviews or do the mental-health exercises that it's honestly kind of weird your company is pushing on you. Everything is managed by a litany of largely indistinguishable software programs with nearly unpronounceable names that are impossible to navigate. For many workers, managers, and even HR professionals, they're deeply frustrating and an enormous time suck. The pandemic and the rise of remote work have only made the situation worse. According to a survey of 2,000 organizations by Sapient Insights Group, a research and advisory firm, companies now use an average of 21 HR "modules" — meaning various apps to conquer different tasks — up from 10.4 in 2019.

"You end up with what I call the 'kitchen drawer' of HR software," said Josh Bersin, a global HR analyst and CEO of The Josh Bersin Co., a consultancy. "You open the kitchen drawer, and you look in there, and you go, 'What's all this stuff doing in here? Where did we get it all?'"

How did we get here? For one thing, the HR-software market is a lucrative one; IBISWorld estimates it's worth $20 billion in the US. It has some big names — Workday, Oracle, ADP — but also a plethora of smaller businesses and platforms, all promising to make managing a workforce better. For companies, managing workers via software instead of human beings is an appealing prospect. Technology and automation have decoupled the size of the company from the number of people required to manage everyone: Instead of having one HR person for every 100 employees, you can, in theory, have one HR person for however big a company gets because of digital systems to handle the scale. The technology is ideally meant to make it so one HR professional can manage administration, compliance, and requests for many more workers than in the on-paper, in-person past.

"HR teams have become more and more lean," said Ashley Herd, the founder of Manager Method, a training platform for managers. "Frequently I talk to companies and they'll have 200, 500 employees, and there's really one or two dedicated HR people, so it's like an octopus." Herd added, "Even with all the technology in the world, an HR person's inbox is crazy."

With fewer dedicated HR workers, many employees are left to fend for themselves. The problem is that each company has its own systems, and businesses aren't investing in training employees on those systems. They've also decimated the ranks of middle managers who might be able to help. People's tenures at work are shrinking, too, meaning that by the time they figure all the systems out, they're on to the next job. This all means that it takes employees longer to get up-to-speed at new gigs and start firing on all cylinders, productivity-wise, because they're wasting all this time figuring out how to do their jobs instead of just doing them.

"The front office now, in addition to doing its day job, has a proliferation of disparate solutions and disparate combinations of solutions at each company to familiarize with and learn how to use," said Zachary Chertok, a research manager for employee experience at IDC, a market-intelligence firm.

Whatever the software, the experience for employees is often not great. It feels like a lot of this stuff is designed for the back office without the front office in mind or by people who just don't really know what a good user experience would be. Management wants to know how many vacation days you took, and it doesn't care if you had fun putting them into the app, so the app designers tend to deprioritize UX for the frontline employees. Even the big, sprawling tools like UKG and ADP can't do everything — Harsh Kundulli, a senior director analyst in the HR practice at Gartner, a consultancy, told me that even companies that have invested in big human-capital-management systems still wind up having to use other HR software to fill in the gaps.

The issue isn't just the people making the programs — it's the companies buying them. Businesses often put various programs and apps in place without enough forethought. They worry about employee burnout, and instead of addressing what's going on with their workers, they toss them a mental-health app that no one will ever actually use. Different leaders come in with different ideas about which programs they do and don't like, and software providers have an incentive to constantly sell businesses new and different features. If your price is going up by 10% every year, you have to have an explanation.

"There are too many technology solutions out there, all claiming to have all kinds of overlapping capabilities," Kundulli said. "Many times, HR leaders do not have the insight into the market to be able to orchestrate or to combine the right types of technologies, so they often end up buying many technologies that have overlapping capabilities with redundancies."

Leaders can get excited about niche systems, too, using the big software for, say, payroll and the smaller, specialized programs for employee training or the initial phases of recruiting. This swinging back and forth makes the whole thing even messier.

"There's this kind of ongoing cycle in software of bundling and then unbundling," said Tomer London, the cofounder of Gusto, a payroll and HR platform for small and midsize businesses. His company is in the business of trying to bundle features into something that is, as London put it to me, as "intuitive, easy to use, delightful" as Instagram, which does sound nice. And hey, maybe they'll get it figured out.

If the HR-software problem were easily solvable, it would probably already be solved. The experts I spoke with about fixes ranged from modestly optimistic to deeply pessimistic about the future of people management by robot. Companies aren't bringing sprawling HR departments back — they're too inefficient and expensive. It's not clear we want to go back to the kind of bad old days of the HR lady filling out your paperwork next to your desk anyway.

"When money's tight and they want to cut costs to demonstrate that they're being responsible to their shareholders, they will put in software," Carrie Bulger, an industrial-organizational psychologist at Quinnipiac University.

Some platforms put a layer over the top of various tools that puts them all in one place so that employees have one portal and don't realize how many different things they're dealing with. It's a sort of artificial Russian nesting doll situation. ServiceNow does that, and some companies have big-enough IT operations that they can create these products on their own, Bersin said — meaning their employees don't have to touch the shit software they're actually using.

As with so many industries, artificial intelligence is also rearing its head. The hope in HR tech is that AI will be a game changer — that it will lead to a data-analysis revolution and create a fleet of digital assistants that can take care of annoying HR tasks so you don't have to. Some people I talked with envisioned AI-powered chatbots that can tell workers how to accomplish tasks — basically, you type in "Where do I see my pay stub?" or "How do I submit my expense report?" or maybe put in your vacation request and get it sent straight to your manager.

"Each tool will have its own version of a digital assistant," Chertok said. "In the near term, you're still going to have to know which system do I go to for what? But the how is not going to be as much of a challenge because the assistant's going to be there to help you through it."

That seems fine and good I suppose, but also, dealing with 10 little chatbots across 10 different tools is not wildly better than where we are. There's a race to see if someone can create a digital assistant to rule them all — Oracle or ADP or Microsoft's Copilot — but for now, there's no clear winner.

Not everyone is so gung ho about AI's potential. AI needs to have a somewhat clean data source where everything is linked and mapped out and connected, which is not a thing a lot of businesses, especially smaller ones, have. Who among us has tried to check some HR policy and been confronted with two dozen versions, the most up-to-date one impossible to tell? The AI might not be able to figure that out either.

"AI's not going to fix all of this until we sit down and go through the process of mapping and connecting the things we need to understand about our employees and what's going to do to our business," said Stacey Harris, chief research officer and managing partner at Sapient Insights Group. "There's so many layers of things that AI has to understand to then be able to predict what that person may or may not do. And each company has its own individual dataset."

Kundulli, from Gartner, said that the AI chatter in HR is at the peak of inflated expectations and that a lot of companies that have bought into the virtual assistants are experiencing buyer's remorse.

"These chatbots often devolved to being FAQs on HR policies," he said. "The results are not the kind of earth-shattering productivity gains that's often sold to HR leaders."

There is one uncomfortable truth here, which is that one way to cut down on the random apps and constant switching would be to have one or two killer solutions that everyone uses, like Microsoft Windows back in the day or Google for search. I'm not promoting a monopoly here, but also, you kind of get why people don't always hate them — they eliminate the hassles competition can create for consumers and can achieve levels of scale and efficiency that deliver people things they really like (see: Amazon in e-commerce). If every time you switched jobs you had the same HR system that you know how to use and that worked really well and remembered you, it would be kind of nice.

But it's not certain a monopoly would even work. Bersin pointed out that PeopleSoft, the IBM-backed HR-management system released in the late 1980s, was supposed to be the be-all and end-all, until it wasn't.

"Everybody loved it. It was really successful. But what they did is as they grew and they started to become very successful, they started to build more and more and more tools on top of it until it also became impossible to use," he said. "It's actually really hard to be a monopoly because the use cases are so varied by industry."

Bersin is in the camp that thinks a bit of disaster is inevitable. "It's going to be a competitive, dynamic, messy market forever, unfortunately," he said.

There are ways to make things better on the margins, but none is a panacea — or within employees' control. Companies can be more strategic about the tech that would be most useful, meaning they make a plan for what they're trying to accomplish. There are some investments that businesses could make to fix things, too — spending that extra 20% to customize the system or putting together readable training materials that actually explain how things work. Of course, that doesn't mean people are going to look at those materials or try to figure things out on their own. Candidly, I've had jobs where I've just given up on certain administrative tasks entirely because I couldn't figure out how to do them and got tired of trying.

And so here we are, doomed to sit in front of our computers wondering whether the "kudos" we were trying to give our coworker, maybe somewhat as a joke, on whatever stupid app that just got rolled out is worth it, as we're 20 minutes into the endeavor with no end in sight. Or maybe someday there will be some killer app that will do it all, or we'll get some AI-powered chatbot to talk to HR about our problems that will make us feel slightly less nuts.