Designing a flexible document organization workflow for estate* lawyers

0-1 application

founding designer

documents

LawyerDoneDeal is a company building legal tech products that optimize workflows for lawyers and law clerks in Canada.

As the lead designer and product owner, I designed a document organization workflow for estate* lawyers.

* the type of law has been altered as a result of a NDA

TEAM:

1 product designer

1 developer

8 legal consultants

PROBLEM

Many real estate law firms have continued to perform accounting bookkeeping processes by hand. However, transactions involving real estate depend largely on cheque handling, requiring writing, sending, and documenting numerous cheques daily with large sums.

Daily manual cheque writing can result in numerous opportunities for human error with large amounts of money on the line.

IMPACT

Beta User Positive Feedback

Two law firms who acted as beta users said the cheque printing functionality significantly reduced the time it takes for their firm to prepare cheques.

MVP Design → New Accounting App

The success of the cheque printing functionality gave the company confidence to build its new trust accounting platform around the same core foundation and functionality.

Improved Design System

I used this project to launch new standards in our design system. These standards have now been added into the design system and will guide future software enhancements.

objective

Design a feature for law firms to print bank account information and amounts on two different types of cheques and ensure the final product complies with legal specifications set by the Canadian Payments Association.

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.

constraints

Firms' bank account information are already saved on the existing software but using legacy code. I will need to integrate this modern cheque printing functionality into an existing legacy workflow.

design exploration

• principles // design north star

Given both the legal and financial landscape of this project, I had to ensure users felt confidence and trust that printing cheques on the software would be legal and bank compliant.

To ensure this message was conveyed to users, I drew on a set of foundational UX psychology practices to guide my design thinking.

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.

• market research

I began looking at similar applications for common workflows and patterns. Interestingly, there were few cheque printing software available. As a result, I looked at industry adjacent software - like word processing.

A common pattern we often use in word processing is choosing to start a document from a blank page, or an established template. I decided to take this as inspiration to begin the cheque printing workflow.

Design exploration to allow users to select template type.

• workflow exploration 1

Using the word processing pattern as inspiration, I decided to design the initial userflow as a gradual process to prevent information overload, where more detailed information is asked gradually throughout the workflow.

• workflow exploration 2

For blank cheques, margin configuration is not as important since the layout can be positioned dynamically to align correctly during printings. However, pre-printed cheques already contain a fixed template on the cheque stock, so users need to ensure their bank details align within the designated printed areas.

Because of this, I added an intermediary configuration screen specifically when pre-printed cheques are chosen, allowing users to adjust and save margins that match their particular cheque stock before printing.

Test prototype to verify workflow with stakeholders.

• iterating post feedback

I tested the prototype with 4 law clerks across 2 law firms in British Columbia resulting in two realizations:

Law firms typically carry only one type of cheque

If firms carry pre-printed cheque stocks, it's rare that they'll have different versions with different fixed templates on them.

Clerks spent a long time aligning margins and conducting test prints

Clerks spent on average an additional 6 min testing out the margins before they were happy with the final product.

With this in mind, I streamlined the workflow by reconfiguring the margin setup steps as an administrative setting such that it only needs to be configured once and is then applied for all users thereafter.

For firms using different cheque stocks across bank accounts, I also allowed cheque configurations to be managed per bank account. This ensures settings are pre-configured in advance, minimizing redundant setup for end users.

Test prototype to verify workflow with stakeholders.

• UI Design decisions

When filling in the cheque details, I designed the interface to visually mirror a real cheque. By aligning the interface to match familiar mental models, this reinforces familiarity, reliability, and trust.

Utilizing UX psychology design principles - match between system and the real world

I aimed to provide the user with immediate feedback whenever possible like allowing them to preview their margin settings and utilizing inline error states to promote user confidence, accuracy, and convey trust.

Utilizing UX psychology design principles - visibility of system status

• design system improvements

Inline error states and matching designs to reality were not design patterns that currently existed within the existing software. I saw this project as a chance to add these features and improve the software’s overall usability in a focused, low-risk setting. These design practices would ultimately end up serving as an implementation guideline for future projects.

Utilizing UX psychology design principles - visibility of system status

• reflection

While adoption has been limited due to many firms relying on external accounting tools, the feature was delivered in just three months by only myself, and one other developer — nearly half the time comparable projects in the backlog had previously taken.

In addition to establishing design practices that guided future projects, this project also delivered meaningful improvements to the platform. It strengthened the software's financial capabilities, improved reconciliation accuracy, and now serves as part of the core package in new product rollouts, helping position the software as a more complete end-to-end solution for law firms.

To support this implementation, I consulted documentation from the Canadian Payments Association and worked closely with the developer to define detailed specifications for this customization functionality.

PROBLEM

Many real estate law firms have continued to perform accounting bookkeeping processes by hand. However, transactions involving real estate depend largely on cheque handling, requiring writing, sending, and documenting numerous cheques daily with large sums.

Daily manual cheque writing can result in numerous opportunities for human error with large amounts of money on the line.

IMPACT

Beta User Positive Feedback

Two law firms who acted as beta users said the cheque printing functionality significantly reduced the time it takes for their firm to prepare cheques.

MVP Design → New Accounting App

The success of the cheque printing functionality gave the company confidence to build its new trust accounting platform around the same core foundation and functionality.

Improved Design System

I used this project to launch new standards in our design system. These standards have now been added into the design system and will guide future software enhancements.

objective

Design a feature for law firms to print bank account information and amounts on two different types of cheques and ensure the final product complies with legal specifications set by the Canadian Payments Association.

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.

constraints

Firms' bank account information are already saved on the existing software but using legacy code. I will need to integrate this modern cheque printing functionality into an existing legacy workflow.

design exploration

• principles // design north star

Given both the legal and financial landscape of this project, I had to ensure users felt confidence and trust that printing cheques on the software would be legal and bank compliant.

To ensure this message was conveyed to users, I drew on a set of foundational UX psychology practices to guide my design thinking.

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.

• market research

I began looking at similar applications for common workflows and patterns. Interestingly, there were few cheque printing software available. As a result, I looked at industry adjacent software - like word processing.

A common pattern we often use in word processing is choosing to start a document from a blank page, or an established template. I decided to take this as inspiration to begin the cheque printing workflow.

Design exploration to allow users to select template type.

• workflow exploration 1

Using the word processing pattern as inspiration, I decided to design the initial userflow as a gradual process to prevent information overload, where more detailed information is asked gradually throughout the workflow.

• workflow exploration 2

For blank cheques, margin configuration is not as important since the layout can be positioned dynamically to align correctly during printings. However, pre-printed cheques already contain a fixed template on the cheque stock, so users need to ensure their bank details align within the designated printed areas.

Because of this, I added an intermediary configuration screen specifically when pre-printed cheques are chosen, allowing users to adjust and save margins that match their particular cheque stock before printing.

Test prototype to verify workflow with stakeholders.

• iterating post feedback

I tested the prototype with 4 law clerks across 2 law firms in British Columbia resulting in two realizations:

Law firms typically carry only one type of cheque

If firms carry pre-printed cheque stocks, it's rare that they'll have different versions with different fixed templates on them.

Clerks spent a long time aligning margins and conducting test prints

Clerks spent on average an additional 6 min testing out the margins before they were happy with the final product.

With this in mind, I streamlined the workflow by reconfiguring the margin setup steps as an administrative setting such that it only needs to be configured once and is then applied for all users thereafter.

For firms using different cheque stocks across bank accounts, I also allowed cheque configurations to be managed per bank account. This ensures settings are pre-configured in advance, minimizing redundant setup for end users.

Test prototype to verify workflow with stakeholders.

• UI Design decisions

When filling in the cheque details, I designed the interface to visually mirror a real cheque. By aligning the interface to match familiar mental models, this reinforces familiarity, reliability, and trust.

Utilizing UX psychology design principles - match between system and the real world

I aimed to provide the user with immediate feedback whenever possible like allowing them to preview their margin settings and utilizing inline error states to promote user confidence, accuracy, and convey trust.

Utilizing UX psychology design principles - visibility of system status

• design system improvements

Inline error states and matching designs to reality were not design patterns that currently existed within the existing software. I saw this project as a chance to add these features and improve the software’s overall usability in a focused, low-risk setting. These design practices would ultimately end up serving as an implementation guideline for future projects.

Utilizing UX psychology design principles - visibility of system status

• reflection

While adoption has been limited due to many firms relying on external accounting tools, the feature was delivered in just three months by only myself, and one other developer — nearly half the time comparable projects in the backlog had previously taken.

In addition to establishing design practices that guided future projects, this project also delivered meaningful improvements to the platform. It strengthened the software's financial capabilities, improved reconciliation accuracy, and now serves as part of the core package in new product rollouts, helping position the software as a more complete end-to-end solution for law firms.

To support this implementation, I consulted documentation from the Canadian Payments Association and worked closely with the developer to define detailed specifications for this customization functionality.

role

I was the sole designer for this project, creating a document organization workflow for lawyers.

I owned the legal research and design end-to-end, independently interpreting and navigating the provincial and federal legislation to transform a complex financial disclosure process into an intuitive experience.

This project is part of a larger 0→1 app that I joined during the proof of concept phase and currently working on refining functionality for launch.

IMPACT

Scaling with Volume

Lawyers did not have a tool that connected disclosure to a compiled, court-ready brief. Each one was built by hand moving through Adobe and Word. This feature reduces the manual steps required per document from 4 to 1, a 75% reduction in manual actions needed to compile a court-ready brief.

At scale, this gap compounds: a 10-document brief requires 40 manual actions under the legacy process versus 10 under the current design.

Industry Validation

In monthly presentations to Ontario estate* law firms and associations, lawyers described the workflow as a "major time saver" and enhanced ability to focus on billable hours. It has now received institutional attention at the firm and judicial level ahead of launch.

* the type of law has been altered as a result of a NDA

problem

To verify their client's net worth, estate* lawyers require collecting a large volume of supporting evidence. Failure to provide complete information has previously been nicknamed the “cancer of family law litigation” by the Supreme Court of Canada.

When I spoke with 8 lawyers and their clerks about this process, everyone mentioned organizing support documentation as the most important step in their workflow, but also the most tedious. The process is uniquely challenging due to strict court regulatory frameworks and administrative burdens. It is manually intensive and time consuming to organize supporting evidence (disclosure) and ensure they are court-ready.

key challenge

Court submissions require a fixed set of categories, but no two firms collect and organize documents the same way. The system had to support both. This meant that I had to simplify the organization process to be easier regardless of firm, but ensure the final output would remain the same.

workflow exploration

To simplify the current workflow, I decided to explore linking uploaded documents to a pre-determined, court-compliant folder on the backend. By pre-organizing, this would help shorten the lawyer's workflow considerably, allowing more time to audit for any changes necessary.

By mapping uploaded documents into pre-determined court-ready folders, this would shorten the lawyer workflow organize support documentation.

• design exploration 1

In my first design, at the point of upload, each line item is automatically linked to a specific court folder as each value a client reports require a supporting document. When lawyers compile a brief (summary) for court submission, all uploaded documentation are already grouped categorically by court name.

Each document has already been mapped relationally to a folder at the point of upload.

Lawyers can upload documentation per line item. Each uploaded document has been mapped to the related court-ready folder.

Each document has been categorized into court ready folders, ready for brief (summary) creation.

Although this design was received well by consultants, this 1:1 relational mapping design did not support nested folders and a more elaborate folder hierarchy structure. After discussing the programming constraints with the project developer, we decided to move the folder structure to Microsoft Sharepoint, which would handle both parent and child folders.

• design exploration 2

On Microsoft Sharepoint, we were now able to pre-define uploaded documents to both parent and child folders. However, this relational mapping disallowed user choice and agency. Lawyers are limited to organizing their documents to our definitions. Which begs the question,

"What if users wanted to upload a document and store it separate from the pre-defined folder?"

If a user created their own folders on Sharepoint, their uploaded documents would not be mapped to the folder we have stored in the backend.

Reframing the Problem / Addressing Earlier Assumptions

I worked through various design options and realized the issue was the assumption I had made at the start: lawyers only want to organize documents the same way the court requires them.

Although the court output is required at later stages, lawyers may not want to organize documents in this strict manner throughout. Forcing this early structure to an everchanging process was the primary cause of the friction.

This meant treating organization and output as two separate concerns, where documents are structured in the way the lawyer works in, and the court format is only applied when a brief is compiled.

Current design

Users have full freedom in creating and naming folders however they want, with no forced mapping to court categories. When it's time to compile a brief, users select the folders they want to submit, download as a complete .docx file and edit as needed to ensure court compliancy.

By adjusting the mapping process to be user-centric, we changed the data model underneath the design, and helped freed the early stages of the workflow from the court's structure.

Revised and current workflow

Users have full freedom in creating and naming folders however they want, with no forced mapping to court categories. When it's time to compile a brief, users select the folders they want to submit, download as a complete .docx file and edit as needed to ensure court compliancy.

By adjusting the mapping process to be user-centric, we changed the data model underneath the design, and helped freed the early stages of the workflow from the court's structure.

User selects which folder to map uploaded document to.

Briefs (summary) can be created regardless of which folder has been selected. All selected items are compiled into a Microsoft Word ouput.

Once downloaded as a .docx file, users can edit headings and text to ensure all items are court compliant.

next steps

This app is set to launch February 2027 and is currently being evaluated at the court and judicial level. At scale, this platform has the potential to meaningfully reduce the administrative overhead while providing smaller law firms another avenue to provide their clients with access to justice.

©2026 debbie

©2026 debbie

©2026 debbie