A Real-World Example of Frustrating Software Onboarding

A young man in glasses, wearing a blue sweater, holds his head in frustration with his mouth open wide, looking overwhelmed. His laptop and documents sit on the desk in front of him, emphasizing a stressful work situation. A perfect representation of software onboarding gone wrong.

Frustrating software onboarding can turn even the best tools into a nightmare. A well-written PDF and a webinar aren’t enough when users still feel lost. I experienced this firsthand when helping a friend with his bookkeeping platform—struggling to figure it out, second-guessing every step, and contacting support multiple times. Then, just as I mastered it, they switched to a new tool… with the exact same onboarding mistakes.

Why do companies keep repeating this cycle? And more importantly—how can we fix it? Read on to discover a better approach to software adoption that saves time, reduces frustration, and actually works.