top of page

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

RocketSign

LegalTech

Rocket Lawyer

E-signature tool faced adoption challenges due to technical bugs and lack of advanced security features compared to DocuSign.

WHAT WENT WRONG

  • Poor technical reliability in signature workflows

  • Limited compliance with advanced legal security requirements

SIGNALS MISSED

  • Reports of failed signature processes during pilot programs

  • Feedback from firms citing security concerns. 

HOW COULD THEY HAVE AVOIDED THIS

  • Enhancing security features to meet legal standards

  • Thorough testing to eliminate technical bugs

TEAMS INVOLVED

Product, Engineering, QA, Compliance

LegalZoom AI Drafting Assistant

LegalTech

LegalZoom

Aimed to help users draft legal documents but struggled with inaccuracies and limited customization, leading to poor adoption.

WHAT WENT WRONG

  • Inaccurate document templates generated by AI

  • Poor fit for nuanced legal scenarios

SIGNALS MISSED

  • Feedback from users indicating errors in drafts

  • High abandonment rates during document creation

HOW COULD THEY HAVE AVOIDED THIS

  • Refining AI models with real-world case data

  • Allowing more customization for specific legal needs

TEAMS INVOLVED

Product, AI, Engineering, Customer Success

Atrium Legal Workflow Automation

LegalTech

Atrium

Promised streamlined legal services through automation but failed due to overpromising and lack of scalable technology.

WHAT WENT WRONG

  • Overreliance on unproven automation tools

  • Insufficient customization for different legal workflows

SIGNALS MISSED

  • Customer feedback about limited functionality

  • Challenges scaling for larger firms with complex needs

HOW COULD THEY HAVE AVOIDED THIS

  • Focusing on niche workflows before scaling

  • Building customizable features for different legal practices

TEAMS INVOLVED

Product, Engineering, Marketing, CEO

Clio Payments (Initial Rollout)

LegalTech

Clio

Clio’s payment processing feature failed to gain traction due to poor integration with existing case management workflows.

WHAT WENT WRONG

  • Weak user experience for payment tracking

  • Limited customization for firm-specific billing needs

SIGNALS MISSED

  • User complaints about payment reconciliation issues

  • Low usage rates in law firms

HOW COULD THEY HAVE AVOIDED THIS

  • Developing seamless integration with existing Clio tools

  • Providing flexible billing workflows for diverse firm structures

TEAMS INVOLVED

Product, Engineering, Design, Marketing

CARA AI (Early Versions)

LegalTech

Casetext

Early versions of the AI-assisted legal research tool failed to provide accurate document recommendations due to insufficient training data.

WHAT WENT WRONG

  • Weak AI training models

  • Limited integration with existing legal research platforms

SIGNALS MISSED

  • Reports of irrelevant or outdated recommendations

  • Low adoption by firms reliant on accurate legal precedent searches

HOW COULD THEY HAVE AVOIDED THIS

  • Testing AI models with diverse and updated legal databases

  • Partnering with existing platforms for better integrations

TEAMS INVOLVED

Product, AI, Engineering, Customer Success

Lexis Advance (Early Versions)

LegalTech

LexisNexis

Early iterations of the legal research tool faced criticism for a clunky interface and limited search functionality, frustrating legal

WHAT WENT WRONG

  • Poorly designed search algorithms

  • Lack of user-friendly navigation and tools

SIGNALS MISSED

  • Feedback from beta users highlighting usability issues

  • Low engagement from early adopters in law firms

HOW COULD THEY HAVE AVOIDED THIS

  • Conducting usability testing with legal professionals

  • Iterating on search algorithms for relevance and accuracy

TEAMS INVOLVED

Product, Design, Engineering, Customer Success

Fractional Executives

© 2025 MINDPOP Group

Terms and Conditions 

Thanks for subscribing to the newsletter!!

  • Facebook
  • LinkedIn
bottom of page