Web app

Productivity

Product Design

2024

How I designed an AI companion feature to end dull
tasks

Researching, UX/UI, Design Handoff

Background

Lawyers who used Lupl needed ways to get more done in less time. I made an AI feature that helped lawyers get their work done faster.

Impact

  • MVP launched within 2 months

  • Helped with expanding the design system into a base that can be used by anyone

  • Made it easier for users to create matters and get useful insights

Problem: unreliable AI output

One major problem was that AI didn't always give the same answer, which could make it hard for prototype designs to work in real life. Another problem was finding the right balance between using contextual AI and handling auto-enabling correctly.

Design explorations

After exploring various design ideas, I reached a point where I felt confident enough. Ready to get feedback on the first designs.

First try:

Prebaked prompts for welcome modal

Context-aware AI for collaborators

Context-aware AI for notifications

Prebuilt prompts for text

Getting feedback

During a feedback session, we concluded that the color I picked didn’t match the brand. It had to stand out, but the above purple was too different from Lupl’s teal identity.


A key takeaway from this meeting was to use familiarity. Since our customers were already using Microsoft Copilot, we decided on this card system for our assistant, as shown below.

Focus change

Although the first designs were inspired by Notion's context-aware AI assistant, things turned out to be different along the way. Due to a development focus switch, the new requirements for a minimum viable product had been much simplified.


The new needs included four types of prompts on the dashboard AI modal. These cards had buttons that let you quickly turn text into tasks in Lupl.

Improvement: Instead of displaying text prompts one by one, they were arranged in cards to make it easier for users to choose.

AI output was simplified to make development easier and create a basic version of the product to test.

Matter-related cards were simplified for the final iteration. They provide quick follow-up
actions for quickly creating items.

Task-related cards are simple and display only the essential information and a progress status.

Lessons learned

Unfortunately, in the end, this feature was completely deprioritized. But the iterative design process helped me gain valuable insights into meeting technical and business constraints.


It helped me develop an agile attitude and become more aware that not all design ideas will make it into production. And most importantly, it gave me an opportunity to learn and improve.

Web app

Productivity

Product Design

2024

How I designed an AI companion feature to end dull tasks

Researching, UX/UI, Design Handoff

Background

Lupl is a tool designed to streamline legal processes and workflows. I build a step feature that turns overload into manageable and enables users to better manage their workload.

Impact

  • MVP launched within 2 months

  • Helped with expanding the design system into a base that can be used by anyone

  • Made it easier for users to create matters and get useful insights

Problem: unreliable AI output

One major problem was that AI didn't always give the same answer, which could make it hard for prototype designs to work in real life. Another problem was finding the right balance between using contextual AI and handling auto-enabling correctly.

Design explorations

After exploring various design ideas, I reached a point where I felt confident enough. Ready to get feedback on the first designs.

First try: Prebaked prompts for welcome modal

Context-aware AI for collaborators

Context-aware AI for notifications

Prebuilt prompts for text

Getting feedback

During a feedback session, we concluded that the color I picked didn’t match the brand. It had to stand out, but the above purple was too different from Lupl’s teal identity.


A key takeaway from this meeting was to use familiarity. Since our customers were already using Microsoft Copilot, we decided on this card system for our assistant, as shown below.

Focus change

Although the first designs were inspired by Notion's context-aware AI assistant, things turned out to be different along the way. Due to a development focus switch, the new requirements for a minimum viable product had been much simplified.


The new needs included four types of prompts on the dashboard AI modal. These cards had buttons that let you quickly turn text into tasks in Lupl.

Improvement: Instead of displaying text prompts one by one, they were arranged in cards to make it easier for users to choose.

Matter-related cards were simplified for the final iteration. They provide quick follow-up actions for quickly creating items.


Task-related cards are simple and display only the essential information and a progress status.

Additional improvements

Unfortunately, in the end, this feature was completely deprioritized. But the iterative design process helped me gain valuable insights into meeting technical and business constraints.


It helped me develop an agile attitude and become more aware that not all design ideas will make it into production. And most importantly, it gave me an opportunity to learn and improve.

Web app

Productivity

Product Design

2024

How I designed an AI companion feature to end dull tasks

Researching, UX/UI, Design Handoff

Background

I improved the checkout page to increase donations for Declic - a non-profit group for online petitions and activism.

Impact

  • MVP launched within 2 months

  • Helped with expanding the design system into a base that can be used by anyone

  • Made it easier for users to create matters and get useful insights

Problem: unreliable AI output

One major problem was that AI didn't always give the same answer, which could make it hard for prototype designs to work in real life. Another problem was finding the right balance between using contextual AI and handling auto-enabling correctly.

Design explorations

After exploring various design ideas, I reached a point where I felt confident enough. Ready to get feedback on the first designs.

First try: Prebaked prompts for welcome modal

Context-aware AI for collaborators

Context-aware AI for notifications

Prebuilt prompts for text

Getting feedback

During a feedback session, we concluded that the color I picked didn’t match the brand. It had to stand out, but the above purple was too different from Lupl’s teal identity.


A key takeaway from this meeting was to use familiarity. Since our customers were already using Microsoft Copilot, we decided on this card system for our assistant, as shown below.

Focus change

Although the first designs were inspired by Notion's context-aware AI assistant, things turned out to be different along the way. Due to a development focus switch, the new requirements for a minimum viable product had been much simplified.


The new needs included four types of prompts on the dashboard AI modal. These cards had buttons that let you quickly turn text into tasks in Lupl.

Improvement: Instead of displaying text prompts one by one, they were arranged in cards to make it easier for users to choose.

AI output was simplified to make development easier and create a basic version of the product to test.

Matter-related cards were simplified for the final iteration. They provide quick follow-up
actions for quickly creating items.

Task-related cards are simple and display only the essential information and a progress status.

Additional improvements

Unfortunately, in the end, this feature was completely deprioritized. But the iterative design process helped me gain valuable insights into meeting technical and business constraints.


It helped me develop an agile attitude and become more aware that not all design ideas will make it into production. And most importantly, it gave me an opportunity to learn and improve.

Thanks for reading

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ana@anaracheleanu.com

©2025 Ana Racheleanu

ana@anaracheleanu.com

©2025 Ana Racheleanu

ana@anaracheleanu.com

©2025 Ana Racheleanu