Improving Chat Organization on ChatGPT through Dual Workspaces, Labels, Pins & Bookmarks, Smart Suggestions, and Advanced Search

UX Research,
Information Architecture,
Interaction & UI Design
Figma, FigJam,
ChatGPT, Freepik,
Adobe Illustrator
Case Study – AI Productivity
Team Project (2 People)

We’ve all been there, scrolling endlessly to find that one helpful ChatGPT conversation.
As ChatGPT becomes part of users’ daily routines, conversations pile up fast. Without a clear structure, revisiting past chats becomes frustrating. Many users resort to screenshots, notes, or external tools just to keep track.
This raised a key question for us :
How can we turn ChatGPT into a space that feels personal, searchable and organized?
This case study explores how smarter chat history, through better search, structure, and personalization, can help users stay on track and actually reuse their conversations.
"If I can’t find an old chat, I just start a new one, it’s faster."
While users appreciate ChatGPT’s helpful responses, they struggle to revisit important conversations. With no clear system to organize or recall past chats, things quickly become messy.

Same Struggle, Everywhere: From Users to Forums

Across platforms like Reddit and Trustpilot, users consistently report struggling to find, organize, and share past chat.



"I created two separate accounts, one for work stuff, one for personal use."
"Search only works if I remember exactly what I typed. If not, I just scroll forever or give up."
"Sometimes I want to share just one part of a conversation, but I have to copy the whole thing."
"I usually copy useful answers to a Word doc or Telegram so I can find them later."
Users avoid search not because it’s useless, but because it doesn’t match how they think, so they scroll or just start over.
Users switch between personal and work use. Sometimes with two accounts, highlighting the need for workspaces, labels, or profiles to manage different contexts.
When users can’t easily save or share parts of a chat, they rely on slow workarounds like copy-paste. Simple tools for organizing and sharing would make ChatGPT far more useful, especially for collaboration.
Users “hack” chat titles by wording first messages carefully or leaving them as-is, showing the need for better tools like tags, folders, or custom titles to organize growing chat history.
Inside the Minds of Our Users
While users appreciate ChatGPT’s helpful responses, they struggle to revisit important conversations. WTo design a more organized and reusable chat experience, we explored how different types of users interact with ChatGPT. Whether they were task-focused or spontaneous, all faced a common challenge: keeping track of valuable information across conversations.ith no clear system to organize or recall past chats, things quickly become messy.

Daniel –
The Multitasker
35 | Office employee
If I got a good answer, I should be able to find it later, not waste time asking again.
He uses two accounts for work and personal use but doesn’t rename chats, making it hard to keep track. Helpful responses are sent to Telegram or pasted into notes, yet he often rewrites prompts because old ones are hard to find. With a cluttered chat history and no way to share just part of a conversation, he needs separate spaces, filters, and a way to bookmark or highlight key messages.

Lena – The Spontaneous Doer
28 | Salesperson
GPT gives great answers, but I wish it were easier to go back to something I saw before.
She uses mainly for personal tasks and deals with them in the moment. She relies on intuition and usually starts a new chat rather than revisiting old ones. When something is useful, She takes a screenshot or copies the content. However, she often struggles to find past responses, scrolling takes too long. She uses tools as needed, without a long-term plan. She needs a quicker, more reliable way to save and access important content.
What Others Do Well And Where AI Chats Still Fall Short
We compared ChatGPT with other AI Chatbots and productivity tools to see what features they’ve nailed and where they still struggle. This helped us identify inspiration points as well as clear opportunity gaps.

Apps like Gemini, Poe, and Coda Ai are already tackling organization by offering:
Privacy-first sharing (customizable link permissions)
Pinned chats (keep key threads front and center)
Clean timelines (simple browsable history even in free versions)
Most AI chat tools like ChatGPT, Claude, and Copilot are fast but unstructured:
No folders or grouping to structure projects
Poor in-chat search, so old insights get lost
Limited chat management, making long-term work a mess
Structure Without Overhead
We mapped dozens of ideas and prioritized them by impact and effort. “Our goal was simple: give users lightweight ways to stay organized, without adding complexity.”
These solutions were grounded in user needs but designed to blend into existing flows,
not disrupt them.
Dual Workspaces
Problem it solves: Mixing personal and work use . What we did: Let users to switch between customizable spaces like “Work” and “Personal” . Why it matters: Reduced context-switching and helped users stay mentally organized .
Label , Pin and Bookmarks System
Problem it solves: No grouping, visual clutter What we did: Enabled folders with optional tags or colors. Why it matters: Gave users a simple way to define their own organization model.
Smart Suggestion
Problem it solves: Users forget to organize at the right time . What we did: Smart Suggestions like “Move this to a folder?” after a good response. Why it matters: Encouraged habit-building without interrupting the flow.
Advanced Search
Problem it solves: Users struggled to find past chats because the search bar was hidden in the sidebar and lacked useful filters. What we did: Moved search to the top and added filters for time, tags, projects, and image search. Why it matters: Makes search easier to find and more powerful, helping users locate past chats quickly.
Making Chat History Work for Users
We redesigned the ChatGPT experience to improve organization, navigation, and context.These screens highlight features like workspace switching, bookmarks, pins, labels, and smart suggestions that help users group conversations by project, space, or tag—turning scattered chats into a structured, reusable experience.
Workspace Enabled Sidebar for Multi-Context Use
To help users manage both personal and work chats, we introduced switchable workspaces in the sidebar. By default, users can toggle between Personal and Work spaces as needed.We also enabled:Custom workspace management: Rename, recolour, archive, or remove spaces. This sidebar redesign gives users clarity, separation, and control, making it easier to stay focused in multi-context scenarios.
Smart Suggestion: Move to Project
Problem
Users often forget to organize chats in the moment, leading to clutter and lost context. Without suggestions, important conversations remain scattered and hard to retrieve.
Solution
To reduce clutter and improve findability, we introduced a smart suggestion that detects when a chat fits a project, tag, or space and suggests organizing it instantly. This helps users quickly assign chats, create new categories, and stay organized without breaking their flow.
Advanced Search
Problem
The original search function was difficult to locate and lacked the advanced tools users needed to find past chats efficiently. Without filters or control over results, users struggled to search by time, project, or content type.
Solution
The search bar is now placed at the top of the app for better visibility. Filters for time, project, tags, and attachments have been added, along with image search, allowing users to upload a screenshot to quickly find the right conversation.
Bookmark with Intention
Problem
Important info often gets buried in long chats. Without a flexible way to save or manage key points, users waste time scrolling or re-asking GPT. And without easy removal, saved content can pile up and become messy.
Solution
A smart bookmarking system lets users save full chats or highlight specific messages. Multiple bookmarks can be managed in one place, and removed anytime, keeping things clear, focused, and easy to return to.
Pin What Matters
Problem
While bookmarks help save specific messages and labels organize chats by topic, users also needed a simple way to keep entire important conversations visible at a glance.Pinning keeps key conversations fixed at the top of the chat list for instant access and can be unpinned anytime to reduce clutter.
Solution
A smart bookmarking system lets users save full chats or highlight specific messages. Multiple bookmarks can be managed in one place, and removed anytime, keeping things clear, focused, and easy to return to.
What we learned
GPT has become a daily utility, like a digital desk, so users should be able to stay in one space where both personal and work needs are met. Our goal was to support that without adding friction.One of the biggest challenges was balancing simplicity with flexibility. Users wanted better ways to organize chats, but too many features risked more clutter. If I were to revisit this project, I’d invest more in usability testing to better understand how users manage clutter after the redesign, ensuring the new features deliver on their promise of simplicity and clarity.