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Top 4 Nightmare Scenarios of Onboarding New Users

Boaz Amidor

When you think back on the nightmares you've had in your life, what's the common denominator? Did you have the dream where you were running in slow motion, being chased by something, and your legs didn't work? How about the one where you're walking through your old high school and you're naked? Whatever it was, it was scary. The rules of the world you knew didn't apply. You were in the realm of the uncanny, and you had no control over it.

A bad onboarding experience can be just like that for a new user. Bad website design, absent customer support, a poorly implemented tutorial, all of this can turn into a Kafkaesque nightmare for the unsuspecting customer.

Here are four of the most common customer onboarding pitfalls in the SaaS world and the equivalent nightmares we've all experienced at one time or another.

1. Stuck on the other side

A long, confusing signup process can confuse the user and make them feel insecure. The signup process can feel like an infinite feedback loop, forcing you to fill out redundant information, to click through seemingly endless, slow loading pages, to be tormented by unclear instructions and broken URLs. It's like a dream where one is running from some kind of threat, trying to open a door but the doorknob doesn't work, trying to knock on the door but their hands are numb and don't work. Everything you want is just on the other side, but it's impossible to get there. You don't know what's going on: you know what should happen, but it's not working and you don't know why. How can you get out?

2. Is there anybody out there?

Slow, non-responsive customer support is a very alienating nightmare. When the user tries to call customer support, and is on hold for what seems like hours. Nobody responds to their emails either. The SaaS company's website is up and it even updates, but nobody responds to user messages. The lights are on, but nobody's home, like a dream where you're in a city and everything is empty. The buildings are intact, the buses and trains are running, there are cold sodas in the fridge at the bodega, but there's absolutely nobody there. It's eerily silent and the user doesn't know what happened. Did the cold war go hot? Did the aliens come? The rapture? Who knows? But you're customer has been left alone.

3. Falling through the world

In life, when the learning curve on a program is too steep, your user can feel very much like the ground broke underneath them. Things were stable. Things made sense. But the user had to learn too much, too fast and now they have nothing to hold onto. Studies performed by WalkMe show that over 80% of what is learned during new user training is forgotten. In dreams, the ground gives out below you and you're plummeting through the sky and you feel the acceleration in your stomach. And then, thankfully, you wake up before hitting the ground.

4. When the masks come off

When a program fails to meet its promises, the reality that your user was promised vanishes, and instead they must deal with the terror of the unknown. Your user was captivated by the words "groundbreaking," "seamless" and "revolutionary." They signed up, they started the onboarding process and now they're terrified that they made the wrong decision. There are dreams which start out normal before taking a turn for the terrifying. It's a normal amusement park until it isn't, your friends and family rip off their human masks, and their teeth are fangs and the roller coaster you're on is descending down into the darkness.

Whoa?! Listen, onboarding can be a scary thing. It's a big commitment. Make it as easy a process as possible for the new user and hopefully, the only thing they'll have to worry about is bad dreams.

Boaz Amidor is Head of Corporate and Marketing Communications at WalkMe.

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Top 4 Nightmare Scenarios of Onboarding New Users

Boaz Amidor

When you think back on the nightmares you've had in your life, what's the common denominator? Did you have the dream where you were running in slow motion, being chased by something, and your legs didn't work? How about the one where you're walking through your old high school and you're naked? Whatever it was, it was scary. The rules of the world you knew didn't apply. You were in the realm of the uncanny, and you had no control over it.

A bad onboarding experience can be just like that for a new user. Bad website design, absent customer support, a poorly implemented tutorial, all of this can turn into a Kafkaesque nightmare for the unsuspecting customer.

Here are four of the most common customer onboarding pitfalls in the SaaS world and the equivalent nightmares we've all experienced at one time or another.

1. Stuck on the other side

A long, confusing signup process can confuse the user and make them feel insecure. The signup process can feel like an infinite feedback loop, forcing you to fill out redundant information, to click through seemingly endless, slow loading pages, to be tormented by unclear instructions and broken URLs. It's like a dream where one is running from some kind of threat, trying to open a door but the doorknob doesn't work, trying to knock on the door but their hands are numb and don't work. Everything you want is just on the other side, but it's impossible to get there. You don't know what's going on: you know what should happen, but it's not working and you don't know why. How can you get out?

2. Is there anybody out there?

Slow, non-responsive customer support is a very alienating nightmare. When the user tries to call customer support, and is on hold for what seems like hours. Nobody responds to their emails either. The SaaS company's website is up and it even updates, but nobody responds to user messages. The lights are on, but nobody's home, like a dream where you're in a city and everything is empty. The buildings are intact, the buses and trains are running, there are cold sodas in the fridge at the bodega, but there's absolutely nobody there. It's eerily silent and the user doesn't know what happened. Did the cold war go hot? Did the aliens come? The rapture? Who knows? But you're customer has been left alone.

3. Falling through the world

In life, when the learning curve on a program is too steep, your user can feel very much like the ground broke underneath them. Things were stable. Things made sense. But the user had to learn too much, too fast and now they have nothing to hold onto. Studies performed by WalkMe show that over 80% of what is learned during new user training is forgotten. In dreams, the ground gives out below you and you're plummeting through the sky and you feel the acceleration in your stomach. And then, thankfully, you wake up before hitting the ground.

4. When the masks come off

When a program fails to meet its promises, the reality that your user was promised vanishes, and instead they must deal with the terror of the unknown. Your user was captivated by the words "groundbreaking," "seamless" and "revolutionary." They signed up, they started the onboarding process and now they're terrified that they made the wrong decision. There are dreams which start out normal before taking a turn for the terrifying. It's a normal amusement park until it isn't, your friends and family rip off their human masks, and their teeth are fangs and the roller coaster you're on is descending down into the darkness.

Whoa?! Listen, onboarding can be a scary thing. It's a big commitment. Make it as easy a process as possible for the new user and hopefully, the only thing they'll have to worry about is bad dreams.

Boaz Amidor is Head of Corporate and Marketing Communications at WalkMe.

Hot Topics

The Latest

Like most digital transformation shifts, organizations often prioritize productivity and leave security and observability to keep pace. This usually translates to both the mass implementation of new technology and fragmented monitoring and observability (M&O) tooling. In the era of AI and varied cloud architecture, a disparate observability function can be dangerous. IT teams will lack a complete picture of their IT environment, making it harder to diagnose issues while slowing down mean time to resolve (MTTR). In fact, according to recent data from the SolarWinds State of Monitoring & Observability Report, 77% of IT personnel said the lack of visibility across their on-prem and cloud architecture was an issue ...

In MEAN TIME TO INSIGHT Episode 23, Shamus McGillicuddy, VP of Research, Network Infrastructure and Operations, at EMA discusses the NetOps labor shortage ... 

Technology management is evolving, and in turn, so is the scope of FinOps. The FinOps Foundation recently updated their mission statement from "advancing the people who manage the value of cloud" to "advancing the people who manage the value of technology." This seemingly small change solidifies a larger evolution: FinOps practitioners have organically expanded to be focused on more than just cloud cost optimization. Today, FinOps teams are largely — and quickly — expanding their job descriptions, evolving into a critical function for managing the full value of technology ...

Enterprises are under pressure to scale AI quickly. Yet despite considerable investment, adoption continues to stall. One of the most overlooked reasons is vendor sprawl ... In reality, no organization deliberately sets out to create sprawling vendor ecosystems. More often, complexity accumulates over time through well-intentioned initiatives, such as enterprise-wide digital transformation efforts, point solutions, or decentralized sourcing strategies ...

Nearly every conversation about AI eventually circles back to compute. GPUs dominate the headlines while cloud platforms compete for workloads and model benchmarks drive investment decisions. But underneath that noise, a quieter infrastructure challenge is taking shape. The real bottleneck in enterprise AI is not processing power, it is the ability to store, manage and retrieve the relentless volumes of data that AI systems generate, consume and multiply ...

The 2026 Observability Survey from Grafana Labs paints a vivid picture of an industry maturing fast, where AI is welcomed with careful conditions, SaaS economics are reshaping spending decisions, complexity remains a defining challenge, and open standards continue to underpin it all ...

The observability industry has an evolving relationship with AI. We're not skeptics, but it's clear that trust in AI must be earned ... In Grafana Labs' annual Observability Survey, 92% said they see real value in AI surfacing anomalies before they cause downtime. Another 91% endorsed AI for forecasting and root cause analysis. So while the demand is there, customers need it to be trustworthy, as the survey also found that the practitioners most enthusiastic about AI are also the most insistent on explainability ...

In the modern enterprise, the conversation around AI has moved past skepticism toward a stage of active adoption. According to our 2026 State of IT Trends Report: The Human Side of Autonomous AI, nearly 90% of IT professionals view AI as a net positive, and this optimism is well-founded. We are seeing agentic AI move beyond simple automation to actively streamlining complex data insights and eliminating the manual toil that has long hindered innovation. However, as we integrate these autonomous agents into our ecosystems, the fundamental DNA of the IT role is evolving ...

AI workloads require an enormous amount of computing power ... What's also becoming abundantly clear is just how quickly AI's computing needs are leading to enterprise systems failure. According to Cockroach Labs' State of AI Infrastructure 2026 report, enterprise systems are much closer to failure than their organizations realize. The report ... suggests AI scale could cause widespread failures in as little as one year — making it a clear risk for business performance and reliability.

The quietest week your engineering team has ever had might also be its best. No alarms going off. No escalations. No frantic Teams or Slack threads at 2 a.m. Everything humming along exactly as it should. And somewhere in a leadership meeting, someone looks at the metrics dashboard, sees a flat line of incidents and says: "Seems like things are pretty calm over there. Do we really need all those people?" ... I've spent many years in engineering, and this pattern keeps repeating ...