5 frustrating employee experiences that demand better solutions

Here’s a first day on the job that’s all too common: You have a desk, but your laptop hasn’t arrived. You get a loaner, but your login credentials aren’t working. A welcome meeting overlaps with a required security training session, and you’re asked to review a 56-page PDF of HR policies by the end of the day. 

First days are always a challenge, but clunky onboarding processes make them needlessly so. Despite a decade of corporate “digital transformation” investment, many types of employee experiences remain overly complex and frustrating. From onboarding to IT support, many processes behind those are still governed by outdated systems and siloed workflows. 

There’s a critical cost to poor experience. Disengaged employees are more likely to leave, less likely to deliver great customer experiences, and harder to replace.  Backed by consistent research that shows how positive employee experience (in tandem with good customer experience) drives revenue and profit, more companies are prioritizing EX improvement strategies—especially those that deploy AI.

“As technology has evolved, manual HR processes have been automated, but they haven’t been reimagined,” says Kathi Enderes, senior vice president for research at the Josh Bersin Company, a leading HR research and advisory firm. “With AI, we’re finding that we have the opportunity to rethink employee experience in a different way—to focus on the outcome we want and redesign the process to achieve it.”

With limited resources, where should companies target their efforts? Here’s a look at five  key employee experiences that IT and HR experts consider top priorities, and some ways AI can bring relief.  

IT support: Simplifying workflows for routine requests

Why should it take days for an employee to get help with a simple password reset? It shouldn’t—but too often it does. 

For companies that aren’t leveraging AI for their employee help desks, the average IT ticket time-to-resolution exceeds 30 hours. Slow IT support is not just a source of frustration; it hurts the company’s bottom line. Employees who can’t update software, connect to networks, access shared resources or replace a malfunctioning laptop can’t do their own work or collaborate on team projects.

Why it’s hard to fix: Legacy tools and systems are pretty entrenched at this point. As such, siloed systems lead to fragmented data and visibility, manual workflows mean slow and inconsistent handling, and repetitive, low-complexity requests overwhelm IT teams.

How AI is supporting improvements: The approval workstreams behind a simple vacation request form an ideal use case for agentic AI, explains Murali Swamanathan, chief technology officer of Freshworks. 

“The power of AI agents is in breaking complex tasks into micro-actions,” he says. “When an employee asks for time off, the agent doesn't just provide information. It reasons through multiple steps—checking your available days based on policies, validating your request, and completing the submission process. AI agents can turn a complex vacation request process into a seamless experience. What used to require multiple systems and manual steps becomes one conversation.”

For companies like Australia’s Village Roadshow—a film distribution and production company and also a customer of Freshworks—AI-powered platforms are improving ticket tracking and prioritization, and providing employees with a self-service knowledge base to eliminate the need to create a ticket in the first place.

Replacing its legacy IT service management tool with Freshworks’ Freshservice platform, Village Roadshow quickly saw a 25% decrease in ticket resolution time—and a 25% boost in employee satisfaction scores. The shift eliminated redundant workflows and improved transparency across teams.

Onboarding: Disjointed, overlapping, and inconsistent demands

A new hire’s first week should build enthusiasm, but too often, it breeds confusion. Small wonder why employees who have a poor onboarding experience are twice as likely to look for a new job within six months.

Why it’s hard to fix: Onboarding touches multiple departments, each with its own systems and timelines, and needs from the new hires. Without detailed orchestration, things fall through the cracks—or are just offloaded to the employee, creating a poor experience at the start.

How AI is supporting improvements: Enderes says AI-powered solutions help unstick these pain points. AI-powered copilots walk new hires through tasks, step by step, reducing confusion and making sure nothing slips through cracks. HR chatbots can provide real-time answers to new hires’ questions, and automated document handling and workflows keep things smooth on the back end.

One promising indicator for implementing these strategies:  80% of new hires onboarded with AI-powered processes report that they are satisfied with their welcome to the company, according to a recent Paychex survey. Better still, they are 30% less likely to quit within a year than those onboarded without it.

 Recruiting: Too long, too opaque, too easy to abandon

As bad as poor onboarding processes can be for employees, new research shows that the hiring experience is often even worse. According to Qualtrics’ 2025 Employee Experience Trends Report, 34% of new hires say that their candidate experience was worse than expected, versus just 15% who say the same for onboarding.

The price tag for companies is steep, with nearly half of prospective hires in in-demand fields bailing on a company due to its frustrating hiring process, according to PwC.

Some of the key hiring frustrations, according to job candidates, are: 

• 49% say process is too long and complicated

• 65% report inconsistent communication from the company

• 40% say the company simply “ghosted” them after second or third round interview

Why it’s hard to fix: Hiring workflows span teams and systems. Bottlenecks appear at every stage—from sourcing to scheduling to communication. Without visibility, recruiters can’t optimize the process.

How AI is supporting improvements: At Darussalem Assets, a financial holding company based in Brunei, AI-powered solutions helped reduced hiring time from four months to just three weeks. AI was used to integrate sourcing, communication, and scheduling into a unified system, eliminating delays and miscommunication. Advanced chatbots answer candidate questions, keep them engaged.

Benefits enrollment: Too many options, not enough clarity

Choice can seem empowering—until there’s too much of it. Bersin’s Enderes recently worked with a healthcare company that offers workers 1,500 different benefits plans to choose from. 

Half of all workers are having bad benefits experiences every year, saying they end up regretting the choices they make during the annual two-week open enrollment period, according to an Equitable study. One primary reason is that it’s a confusing, complex process, with one in five workers saying they “just didn’t understand” what their options were. Nearly two-thirds of workers say that a poor benefits experience would cause them to look for a new job.

Why it’s hard to fix: HR teams want to accommodate a diverse workforce, so they offer a vast array of plans—but without tailored guidance, the result is cognitive overload.

How AI is supporting improvements: Today’s AI chatbots are helping uncomplicate the process by providing 24/7 support, guiding employees through the enrollment process, and offering personalized recommendations based on their demographics, lifestyle needs and past benefits usage.

AI-driven benefits enrollment is paying off at companies like IBM, where it has led to a 20% boost in employee satisfaction. And employees are increasingly turning to AI chatbots for guidance in the open enrollment process, with almost one in five open to using them in 2025, double the number from 2023.

Time-off requests: Unclear processes, unmet expectations

Nearly half of all employees don’t use all of their paid time off because they’re afraid of falling behind at work, missing out on future promotions, or overburdening their coworkers, among other reasons, according to a recent Pew study. For many, simply completing a vacation request is difficult.

Why it’s hard to fix: Approval chains are often opaque, and policies may vary across teams. Without clear ownership or automation, small requests get stuck in limbo.

How AI is supporting improvements: AI-powered platforms are increasingly offering the solution by providing one-stop, near-instantaneous processing of approval requests. For time-off requests, this can include automation and routing of requests, and real-time visibility into team calendars and conflicts. New research from Bersin finds that AI-powered chatbots can reduce the time it takes, on average, for an employee to resolve an HR transaction like a time-off request by 90%.

Time-off approval might seem like a minor headache compared with hiring, onboarding and benefits enrollment, but for employees, a company’s ability to alleviate pain points is a huge relief, and AI-driven tools are proving to be powerful medicine.