Notewell AI
Designing a Context-Aware AI Assistant for Social Workers
CONTEXT
How might we turn a disconnected AI chat into a truly helpful tool for social workers?
Notewell is a HIPA-compliant note-taking tool designed to help social workers document client sessions through voice and AI.
While the product already included an AI chat on desktop, it wasn’t designed to support real workflows: there were no persistent threads, no memory, and no way to tie a conversation to a specific client or meeting. Users had to reload context manually every time, and any chat disappeared as soon as they navigated away.
As we worked to bring Notewell to mobile, we saw a chance to do more than just replicate the feature — we wanted to redesign it from the ground up to feel contextual, connected, and actually useful in the moments social workers needed it most.
TYPE
Enterprise SaaS, AI-assisted productivity, Healthcare
PLATFORM
Mobile
TEAM
2 Product Designers, 3 Engineers, 1 Founder
TIMELINE
June 2025 - August 2025 (3 months)
Discovery
I collaborated with the team to pinpoint the limitations of the desktop AI chat. To guide our direction, we interviewed a few of Notewell’s clients — mostly social workers to understand how they used the AI chat, what was missing, and where it could improve.
The takeaway was clear: the AI felt disconnected from their actual work. They wanted to tie questions to specific meetings or clients, revisit past conversations, and rely on the AI to understand context without constant re-explaining.
From there, we explored how the experience could become more intentional, contextual, and naturally integrated into their daily workflows.
Starting Point
Before redesigning the AI chat experience, we took a closer look at how it worked on desktop. While the feature was functional, it lacked the structure and context users needed.
From a meeting note, clicking into AI chat opened a separate tab — but the user had to manually reload the note for context. Threads weren’t saved, client information wasn’t recognized, and conversations disappeared as soon as the page was closed. There was no sense of continuity or awareness of the user’s workflow.
This became the baseline we set out to improve.
Design Principles
To make Notewell’s AI Chat more useful, intuitive, and trusted by social workers, we focused on:
Context driven AI
AI should understand who the user is working with and what meeting it’s referencing — not start from a blank slate every time.
Make AI part of the workflow
The experience needed to live where work happens — inside clients and meeting notes — not in a seperate screen that required extra steps.
Quick access & meaningful chat history
We had to support one-off questions while still giving users a way to revisit and build on past conversations, without clutter or confusion.
DESIGN
Rethinking Notewell’s Chat Model + Entry Points
When we started, Notewell’s AI chat worked identically everywhere — always launching a new, temporary thread with no memory or link to a client or meeting. But user interviews quickly revealed that context was key to making AI truly useful.
We redesigned the chat model around three distinct entry points, each optimized for a specific need:
General: Accessed from the main nav. Automatically opens a new thread, designed for quick, one-off questions.
Client-based: Accessed from within a client profile and are tied to the context of that specific client.
Meeting-based: Accessed from a meeting note and stays anchored to that meeting, ideal for recaps or follow-up planning.
Entry point 1: Navigation tab
Best for quick questions
Entry point 2: Client profile
Persistent chat tied to client
Entry point 3: Meeting note view
Anchored to a specific session
Embedding AI Seamlessly into the Workflow of Social Workers
The first mobile release of AI chat carried over many of the desktop version’s limitations — every request started from scratch, threads disappeared when closed, and users had to manually reload client or meeting context.
For social workers, jumping to a standalone chat screen felt disruptive. We reimagined the experience by embedding AI directly into client profiles and meeting notes as a dedicated tab. This kept the chat anchored to its context, allowing users to review notes, summarize meetings, and ask follow-ups — all without breaking their flow.
Before
· AI Chat opens new screen, losing context
· Manually load context each time
· No history, threads disappear
After
· AI Chat in tabs, reference context in same screen
· Context loaded automatically
· History of chats preserved
Designing a faster, simpler way to give AI the right context
We learned through user interviews that social workers expected the AI to “know” which client or meeting they were referencing, even in general chat. Without that context, responses often felt vague or irrelevant, and adding the necessary details each time was tedious. Contextual awareness is a core selling point for Notewell, so I designed a lightweight flow that allowed users to attach a client or meeting note before submitting a question.
The original desktop approach used a modal, but on mobile this felt clunky and disruptive. I proposed a bottom sheet — a native mobile pattern that kept the interaction smooth and in-flow — and ensured it could scale to support both clients and meeting notes. This approach not only made general chat more relevant, it became the standard for adding context across the app.
Designing for AI Trust & Clarity
Most social workers we spoke to had tried AI tools like ChatGPT but rarely used them for work — citing privacy concerns, vague responses, and the need to constantly re-explain context.
To build trust, we grounded the experience in clarity and transparency. A welcoming message and HIPAA-compliant badge established credibility. Prompt suggestions encouraged exploration, while contextual labels and in-line explanations made it clear how and why the AI was responding — turning an unfamiliar tool into something transparent, helpful and safe to use.
Centralized AI Chat History
We initially faced internal hesitation about including a centralized AI chat history. The founder felt the existing entry points — client profiles and meeting notes — were enough, and viewed general chat as a space for quick, disposable questions.
But early feedback made it clear: users wanted to revisit all conversations, including general ones.
Rather than just segmenting history by chat type — which felt clunky — we reframed the challenge: How might we surface past chats effortlessly, regardless of where they started? This led to a unified, lightweight system that felt familiar, flexible, and easy to navigate.
FINAL DESIGN
Context-Driven, Trusted AI Chat
The final mobile experience turns AI chat into a reliable, context-rich assistant. Anchored directly within client profiles and meeting notes, conversations persist across sessions and are always tied to the right casework. A unified history surfaces all past chats by recency, making it effortless to pick up where you left off. The result is a tool that feels less like a separate feature and more like an integral part of their daily workflow.
CONCLUSION
Project Reflections
This project pushed me to balance product vision with real-world workflows. Early on, the founder saw AI chat as disposable — but user feedback showed its potential as a lasting, context-aware record. Navigating this meant designing for both speed and depth, advocating for features like persistent history and context selection that could scale across the app.
I learned how critical it is to embed trust into AI experiences through clarity, transparency, and seamless integration into the tools people already use. The result is a chat system that social workers can rely, and a foundation we can build on for even smarter AI support.