What Went Wrong...
Examining the missteps of various software products across industries reveals common pitfalls that can derail even the most promising innovations. From inadequate market research and poor user experience design to insufficient testing and failure to adapt to technological advancements, these challenges underscore the importance of thorough planning and execution. The following section outlines specific cases, offering insights into how these factors contributed to their downfall and the lessons that can be gleaned to inform future endeavors.
Available Lessons:
200
Duolingo Bots (AI Chat Feature)
EdTech
Duolingo
AI-powered bots designed for conversation practice failed to meet user expectations due to limited language capabilities.
WHAT WENT WRONG
Poor AI training and inability to handle natural conversations
Limited real-world usability for learners
SIGNALS MISSED
Early user frustration with repetitive and robotic responses
Low adoption rates for the feature post-launch
HOW COULD THEY HAVE AVOIDED THIS
Iterative AI testing with real learners before rollout
Narrowing focus to improve specific conversational use cases
TEAMS INVOLVED
Product, Engineering, AI, QA, Design
AltSchool Personalized Learning Platform
EdTech
AltSchool
A high-tech learning platform aiming to reimagine classrooms failed due to excessive costs and unclear value to schools.
WHAT WENT WRONG
Overengineered software that was too expensive to scale
Poor alignment with existing school workflows
SIGNALS MISSED
Early user feedback indicating steep learning curves
Limited school adoption due to high costs
HOW COULD THEY HAVE AVOIDED THIS
Building scalable, affordable solutions tailored for public schools
Partnering with educators to align features with needs
TEAMS INVOLVED
Product, Sales, Marketing, CEO, Operations
Knewton Adaptive Learning Platform
EdTech
Knewton
Promised AI-driven personalized learning, but the software failed to deliver meaningful results and was too complex for educators to use effectively.
WHAT WENT WRONG
Overpromised AI capabilities without real-world validation
Poor user experience and lack of teacher integration
SIGNALS MISSED
Teachers reported difficulty integrating the platform into curriculums
Low engagement and measurable improvement for students
HOW COULD THEY HAVE AVOIDED THIS
Conducting pilot tests with educators for usability feedback
Aligning AI development with proven learning outcomes
TEAMS INVOLVED
Product, Engineering, Marketing, Sales, Design, CEO
Bridge (Employee Learning Platform)
EdTech
Instructure
Instructure’s corporate LMS failed to compete with enterprise-focused tools due to lack of features and customer traction.
WHAT WENT WRONG
Misunderstanding enterprise customer needs
Slow product evolution compared to competitors
SIGNALS MISSED
Feedback showing feature gaps for corporate users
Low renewal rates during early customer pilots
HOW COULD THEY HAVE AVOIDED THIS
Conducting competitive analysis before launching
Building a feedback loop with enterprise clients for improvements
TEAMS INVOLVED
Product, Sales, Marketing, Engineering
Blackboard Learn Ultra
EdTech
Blackboard
The revamped version of their LMS (Learning Management System) faced delays, bugs, and usability issues, causing frustration for institutions.
WHAT WENT WRONG
Rushed launch with incomplete features
Failure to improve outdated user experience
SIGNALS MISSED
Beta testers reported numerous performance bugs
Negative user feedback on navigation and usability
HOW COULD THEY HAVE AVOIDED THIS
Phased release with rigorous QA testing
Continuous user testing for real-world educator feedback
TEAMS INVOLVED
Product, Engineering, QA, Customer Success, Design
GreenSky Loan Processing Software
FinTech
GreenSky
GreenSky’s software for approving home improvement loans faced bugs that led to misapproved or delayed applications, triggering customer frustration.
WHAT WENT WRONG
Software logic errors in loan approvals
Weak monitoring of partner bank integrations
SIGNALS MISSED
Partner bank complaints about approval inconsistencies
Rising borrower dissatisfaction post-application
HOW COULD THEY HAVE AVOIDED THIS
Frequent audits of approval logic and system integrations
Building real-time dashboards for error detection
TEAMS INVOLVED
Product, Engineering, Risk Management, Operations