Litera Check is a key product in the Litera document lifecycle suite of tools. This project combines many products from BestAuthority, CleanDocs, Contract Companion, and DocXTools. It puts them all into into a new Microsoft Office 365 cloud tool.

Background
Litera Check is a core product falling under the Drafting pillar of tools. It combines many key products used by lawyers to check and proof their contracts with, picking up errors and managing everything from Tables of Authorities, Definitions, Names Dates & More as well as solving Numbering issues. All these solutions, which are VSTO Add-On's, each need separate installers for access.

Objective
The main goal for this large project was to combine the best of these separate old products. They would be combined into a better cloud-based solution - Litera Check. A particular focus was on simplifying & streamlining the lawyer's workflow and improving efficiencies for lawyers themselves to use them more. Moving to a cloud solution also helps. It makes the product suite platform agnostic and available to Mac and PC users. 
An agency in the US conducted some sound research that our team inherited in 2022. They interviewed and connected with 20+ clients, building user journeys and user personas. My team and I maintained and updated these outputs. We did so as products and technologies changed. Below is a small snapshot of the starting contract journey. It shows the various steps of the process. Who engages, when and how they interact (actions) with products (touch-points), pain-points that need solving and opportunities for each phase of the process.
My Role
As the project's design lead, I was in constant contact with the VP of product, the product owner, and many development leads from the different products we were unifying. Creating the go-forward information architecture and using customer research to plan and prioritise products & features. Helping with the epic/story writing. We add Gherkin stories and acceptance criteria (AC) to Jira tickets.
We largely skipped wire-framing and instead used our design system to design high-fidelity prototypes to test and develop from. A contractor initially did the interface designs, and the talented Sumit Dekavadiya, Senior UI/UX Designer at Litera, later continued the work. In addition to helping with design and strategy, I actively participated in user testing the prototypes with clients and internal subject matter experts to ensure that we were addressing pain-points and simplifying the products effectively.
I was also responsible for SUS (System Usability Score) testing the Figma prototypes as they evolved. The score was encouraging, hovering at the high 70's mark*. 70 - 100 is generally considered acceptable. 
*These scores however did not incorporate the new "stacked" Active Drafting feature explained below.
The Challenge
We faced a few challenges in this large piece of work. Much of the O365 cloud APIs were still being developed. This meant lots of compromise and technical limitations. We were in constant contact with Microsoft and closely watched their release cycles which we always waited on with anticipation. More advanced API's meant more functionality and improvements to usability. These constraints helped us prioritise products and functionality to focus on. 
We pushed technology boundaries and prioritized user experience in every design. 
With a large user base already using the various Drafting VSTO tools, we made sure not to stray too far from the existing patterns that users were used to. We spent a lot of time testing different interfaces and workflow options with our users. A big takeaway from the research was that users wanted flexibility. They wanted to customize interfaces and workflows. Speed however remained the dominant request. 
As few clicks as possible to complete a task!
During the user research, I was with some of Litera's lawyer clients. I asked them more questions about their workflow. I asked how they, as lawyers, proofread contracts. Some would rely on our drafting tools to find issues. But, most would still prefer to read the document from top to bottom. The current point solution had an Active Drafting feature. But, it was hidden and under utilised. It would allow the issues to be presented as colour-coded text in the document itself. Clicking on them would help them resolve the issue in the task pane. This feature had many pain-points. We spent time on a new workflow for Active Drafting. Below is the quick concept our team put together to test. Praise dominated the feedback.

With this new workflow our team has been able to add a far faster & simpler way to solving multiple issues across all categories.
Our action panel organism which is built into Litera's Design System is the hero in this new workflow. Presented as stand alone cards which appear chronologically as the issues arise in the document. They disappear with a single click decision from the user helping to get through multiple issues at speed in a gamification kind of way.
The Outcome
In Q2 of 2024, Litera released a beta of the Drafting Cloud tool to a select group of customers. The purpose was to do more user testing. QE meticulously tested it.  Our design team examined each element, confirming that custom-built Drafting organisms operated correctly. One of the many constraints of the O365 add-in is that the starting width of the add-in panel is fixed at 320 pixels. We couldn't customise it. We added a short animation. It reminds our users that they can expand the window. Our Pendo integration guided users through the new interface and features. It did more of the onboarding process to help with user adoption.

Going forward
Litera will conduct an assessment of the new Active Drafting Stacked tool. Based on the results, they are likely to add it as an optional new workflow for users. Litera is also moving away from taking over the Word ribbon. Most lawyers prefer to still use the Word toolbar to edit documents. All shortcuts and Litera functionality will be in the task bar. It will have a simple Litera Add-Ins launch button in the ribbon. 
In early 2024 I led a vision sprint. My team designed many happy flows. They told a compelling story of the whole lawyer process. It showcases how all the Litera products would be useful. They are useful at the different stages - from winning business to final settlement. I will be adding this as a separate project shortly.