Founding Designer
LawyerDoneDeal is a company building legal tech products that optimize workflows for lawyers and law clerks in Canada.
As a product designer, I designed and shipped an MVP feature for law firms to print bank-standardized cheques right from their computer.
TEAM:
1 product designer
1 developer
1 business development manager
Photography
Role:
user research
end to end design
Product Management
Development Handoff
PROBLEM
Canada's family law software market has one dominant player charging over $200 per user per month, leaving smaller firms underserved. Many of these firms already use LDD's real estate software, making family law a natural expansion.
When I spoke with eight Ontario lawyers, every single one described the same experience: gathering and organizing client financial documents is the most critical part of their work, and the most tedious. Clients rarely provide everything the first time, leading to repeated phone and email follow-ups. Once documents arrive, lawyers manually sort them into court-mandated categories before compiling them into briefs.
IMPACT
impact title
The product is in active development with two developers implementing the latest workflow. Despite being pre-launch, it is attracting institutional attention — LDD is in discussions with large Ontario law firms, holds monthly meetings with a provincial lawyers' association, and has engaged with sitting judges.
Planned future enhancements include a client portal that auto-populates the lawyer's workflow, secure document sharing with opposing counsel, and AI-assisted extraction of key information from supporting documents.
objective
Design a system that simplifies document organization for lawyers while working within the constraints of how documents must be presented in court.
Law firms have a choice between carrying pre-printed or blank cheques. File information will need to print perfectly in each section, compliant with measurements set by the Canadian Payments Association regardless of cheque type.
design exploration
•iteration 1- Automatic Court-Folder Mapping
My first design automated the entire process. Each supporting document attached to a financial line item would map automatically to the correct court folder on the backend. By submission time, documents would already be sorted. Legal consultants loved the prototype — it was seamless and required no extra effort from users.
When development began, the complexity of managing subfolders broke the model. We moved the folder structure to SharePoint to solve it.
Match between system and the real world
Matching physical cheque layouts builds on user familiarity to reduce the learning curve and reinforce confidence in the feature’s legal compliance.
Visibility of system status
Reassures users they’re filling in the virtual cheque correctly by providing clear, continuous feedback that guides them through a new workflow.
•iteration 2 - Drive-Style Folders
The SharePoint approach introduced a familiar drive interface, but created a new problem: users naturally expect to create and rename folders in a drive. Any custom folder broke the automatic mapping. A middle-ground where users could opt out of automation wasn't a satisfying answer.
Design exploration to allow users to select template type.
Iteration 3 — Pre-Mapped Folder Settings
Asking users to configure their folder structure upfront preserved the mapping logic, but required too much foresight early in the workflow and became increasingly inflexible as files progressed.
• the lightbulb moment
After three failed iterations, I identified the real issue: I had assumed lawyers would want to organize documents to match court requirements from the start. That assumption was wrong. Lawyers collect first, work through the file, and organize for court only at submission time.
Test prototype to verify workflow with stakeholders.
• iteration 4 - User-Controlled Folders with Court Compilation
The current design gives lawyers full control to create and name folders however they want throughout the file. When it's time to submit, they select the folders they need and rename them to match court requirements. Five lawyers reviewed the prototype and responded positively.
Test prototype to verify workflow with stakeholders.
• reflection
This project required a level of ownership I hadn't exercised before — designing from zero in a regulated domain while managing delivery, conducting research, and contributing to the codebase simultaneously.
The biggest lesson was recognizing when a design problem is actually a framing problem. Three iterations collapsed not because the interface was wrong, but because the core premise was. Learning to step back and challenge the assumption — rather than continue iterating on it — was the most valuable thing I took from this project.