How might we transform a struggling file storage system into an intuitive hub that supports growing user needs? How might we address fundamental structural issues when iterative refinement isn't enough?
As the product designer on Drive's cross-functional team in 2018-2019, I faced the challenge of improving our evolving file storage solution. Drive launched as a simple home for worksheets, but quickly evolved into a hub for file management similar to Dropbox or Google Drive.
As Drive integrated with other applications, its requirements grew exponentially, but the product's functionality and design hadn't kept pace with these expanding needs. What began as iterative improvements eventually led to a collaborative, comprehensive redesign approach with senior design partnership and development team alignment.
My journey through this redesign challenged me to grow beyond incremental improvements, embrace collaboration, and advocate for the comprehensive transformation needed to address core usability and performance issues.
Problem Space
The product faced three core challenges:
Performance Issues: Drive wasn't architected for the growing user base and file volume, resulting in significant loading times and user frustration.
Inadequate Core Functionality: The system struggled with basic file management tasks:
Ineffective search capabilities
Limited organization options (files existed only in an "all files" section)
Unclear action icons that confused users
Technical Limitations: The existing architecture constrained potential design solutions, leading to constant compromises and edge case management.
Old Drive design and core functionality issues
Initial Approach
As the designer on a cross-functional team, I initially tackled these issues through iterative refinement, focusing on UI improvements and layout redesigns. However, this approach proved insufficient for addressing the fundamental structural problems. Despite multiple redesign attempts, I found myself in "design churn purgatory" with minimal forward progress.
Proof of design churn purgatory!
Turning Point
The breakthrough came when I recognized that small solutions wouldn't solve large structural problems. I approached my manager for support, who validated that the challenge was indeed larger than anticipated—this wasn't a personal failure but a recognition of the problem's scope.
This led to a pivotal collaboration with a senior designer. Together, we realized that iterative refinement wasn't the answer. We needed to be bold.
Strategic Pivot
We made three critical decisions:
Blue Sky Redesign: Rather than incremental changes, we envisioned the best possible version of Drive without initial constraints.
Cross-Team Alignment: We recognized that a comprehensive redesign required support across teams and close collaboration with development.
Technical Reimagining: Coincidentally, the development team had reached similar conclusions about the product's limitations and was planning a complete re-architecture.
Collaborative Breakthrough
This alignment created a perfect opportunity:
I participated in re-architecture meetings to ensure UX considerations were central to the rebuild
The redesign aligned with future directions for the Canvas design system
Pairing with a senior designer allowed for knowledge exchange and mentorship
High-fidelity designs of the new Drive
Outcomes
The redesign journey resulted in:
A More Robust Product: Drive was redesigned to handle current needs and accommodate future growth.
Improved User Experience: The core functionality issues were addressed with intuitive solutions for file finding, organization, and actions.
Personal Growth: Through collaboration and challenging "collisions of ideas," I developed significantly as a designer.
New Drive in production with improved core functionality
Key Takeaways
Reframe Failure as Opportunity: What seemed like design failures were actually indicators of the problem's true scope.
Value of Collaboration: Asking for help wasn't a sign of weakness but recognition that diverse perspectives lead to stronger solutions.
Importance of Alignment: Cross-functional buy-in was essential for implementing bold solutions.
Be Bold When Necessary: While incremental improvement has its place, fundamental problems require comprehensive solutions.