Microsoft Contracts
Modernizing a legacy platform with AI
Microsoft’s platform for managing over 1 million contracts had become outdated and hard to navigate, forcing teams to spend significant manual effort just to find what they needed. I redesigned the entire experience end to end and introduced an AI agent to make finding and managing contracts fast and intuitive, now seeing 30,000 visits a month. Built first as an internal platform, it was then rolled out to outside counsel and served as the blueprint for features added to SharePoint Premium’s legal offerings.
- Role
- Lead Product Designer
- Years
- 2026
- Scope
- Strategy, UI/UX Design, Research
Challenge
With no dedicated researchers, I had to learn and understand complex legal workflows before redesigning anything. The challenge was to speed up task completion, saving time and money on outside counsel without disrupting existing user workflows.
Impact
0 Million+
Contracts Managed
0+
Monthly Visits
0% Faster
Task Completion
0+ Hours
Estimated Annual Savings
Collaboration
As lead product designer, I collaborated directly with business stakeholders, PMs, and engineers from vision through execution, keeping design aligned with business goals and technical feasibility at every step. I also owned the research myself, ensuring the redesign was grounded in real user workflows rather than assumptions.
Designing for an Existing Userbase
Microsoft Contracts manages every non-revenue contract at Microsoft, and two groups do that work using the platform differently.
User Type 1
Paralegals
Paralegals handle most of the daily volume, covering contract research, discovery, and lifecycle management.
User Type 2
Supervising Attorneys
Attorneys supervise teams of paralegals, managing workloads and deadlines, and step into the daily work when needed.
User Type 1
Paralegals
Paralegals handle most of the daily volume, covering contract research, discovery, and lifecycle management.
User Type 2
Supervising Attorneys
Attorneys supervise teams of paralegals, managing workloads and deadlines, and step into the daily work when needed.
Talking to Users and Stakeholders
The senior product manager and I interviewed users to understand where the previous platform failed them, and met with business stakeholders to collect all necessary requirements.
Questions for Users / Business
“Can you walk me through how this platform is used today?”
“What is the current platform missing that you need most?”
“What specifically would you want an AI experience to help you with?”
“What current functionality would you not want us to disrupt?”
“If we could only fix one area of the platform, what would it be?”
“Where is time being lost across the current platform?”
“Where does the existing platform slow you down the most?”
User Pain Points
From several interviews with paralegals and attorneys
Business Requirements
From planning meetings with CELA business stakeholders
Auditing the Existing Experience
Working with a senior product manager, we audited the existing experience, marking what failed users and what was worth keeping.
Notes
Look & Feel
- Super old and outdated
- Warped legacy illustrations
- No strong visual hierarchy
- Not compliant with MS Fluent 2 standards
Notes
AI Contracts Agent
- No current entry point
- Needs to be prominent
Notes
Create Flow
- Still needs to be there
- Needs to have a single entry point
- Not multiple entry points
Notes
Statistical Overview
- This stat has also been de-emphasized
- Need a dedicated stats section
Notes
Legal Review
- Is getting approval on created drafts
Notes
Manual Search
- Need entry point to legacy experience
- De-emphasize it but still visible
Notes
Statistical Overview
- These 2 stats are no longer a priority
Notes
Store Only
- This is just uploading contracts from your device to the database
Notes
Send for Signature
- Once a contract is signed the signed version is stored in the database
Exploring Two Strategies
Before committing to a redesign, we explored adding AI and improved search to the existing platform. Quick explorations of each showed the redesign was the right call.
A temporary solution that might work in the short term but wouldn’t meet all the needs of users
More effort but worth it to address all of the users’ pain points and actually meet business goals
Working with the Legacy Experience
Dashboard Redesign Wireframe
Design Process
A look at my design process, from sketch to wireframe to final high-fidelity design, as well as a comparison to the legacy experience.
Initial Sketches
Wireframe
Final Design
Before
After
Getting Pushback from Users
Some features got pushback when I put them in front of users. I took the feedback and made adjustments to meet their needs.
Modal slows users scanning multiple contracts
Users can quickly navigate contract metadata/summaries
Before Feedback
After Feedback
Narrow sidecar agentic AI chat interface
Fullscreen agentic AI chat interface
Before Feedback
After Feedback
Key Features
Key Features
Dashboard
A summary of everything you own, status, spend, and upcoming renewals. Recent activity and the contracts that need attention sit below.
Contracts Data Grid
A data grid housing every contract the user has access to, with intuitive search and filter capabilities, modernizing a legacy experience.
New Contract & Approval Flow
New contracts start from a legally approved template. Users populate the correct terms and metadata, then create a draft and send it for approval.
Document Panel & Signature Flow
Users get all important contract metadata extracted, an AI summary, any anomalies flagged, and a timeline of its lifecycle. They can send for signature right from the panel.
Purpose-Built Agentic AI Experience
A lot of effort went into how answers read, what they cite, and how they organize information. Users were already reading walls of contract text, so an agent that serves more of it solves nothing. What was previously an eight-minute task can now take under 60 seconds using the Contracts agent.
Custom Components for the Contracts Agent
I designed five custom adaptive cards specifically for the Contracts agent, each built around a recurring moment in the contracts workflow that users encounter.
Building the Contracts Component Library
I put together a component library for Contracts that sits within Microsoft's global Fluent 2 design system. It prevents visual drift, keeps the platform easy for other designers to pick up and maintain, and makes handoff simpler.
Notifications Beyond the Platform
Important moments reach users as adaptive cards in Teams and Outlook, where they're already working, and connect with other platforms in the SharePoint Premium Legal Suite.
AI Making an Impact
AI collapsed the gap between design and code. I moved from Figma to a working demo fast enough to get business sign-off, then handed the frontend UI straight to engineering.
Results After Launch
0/100 (A)
SUS Usability Score
0%
AI Agent Adoption
0%
Growth in Total Usage
Colleague Feedback
Feedback from leaders and partners I worked with on the project, shared during performance reviews.
Charles stepped in without hesitation and delivered. He brought a fresh and thoughtful perspective on every request, proposed multiple well-considered design options, and turned things around at an incredible pace.
Senior Product Manager
Microsoft
A standout strength of Charles is his ability to deeply understand and balance both PM and SWE needs. His collaborative mindset, responsiveness, and design leadership made a significant difference.
Principal SWE Manager
Microsoft
