The Organizational Gap in Teams
Users of Microsoft Teams often struggle to organize and retrieve important conversations with other users spread across multiple chats quickly and efficiently. The current organizational features — pinned chats, search, and saved messages — are not sufficient when it comes to locating important information within chats. This leads to user frustration, reduced productivity, and wasted time for those who use Teams on a daily basis for communication.
My Process
A five-phase approach guided the research from initial discovery through prototype iteration and usability validation.
Discover
Define the research goal and identify target user types
Define
Formulate learning objectives and interview guide
Ideate
Conduct 45-minute interviews with 6 participants
Design
Synthesize findings into insights, persona & two prototype iterations
Test
Usability test with the same 6 participants across both prototype versions
What We Set Out to Learn
Nine targeted learning objectives guided the interview sessions, covering communication patterns, mental models, and pain points across the Teams experience.
💬Understand how people communicate with others in a work environment
⏱️Learn when people initiate communication with others in a work environment
🗂️Understand the types of conversations people have and how they organize them
🧠Understand mental models users have with chat management
🔁Learn when and why people need to revisit communications with others
🔍Explore the pain points users face when searching for or retrieving old messages
⚡Determine if those pain points affect productivity and workflow
Where Teams Stands Against the Competition
Compared to Slack and Google Chat, Microsoft Teams has meaningful enterprise advantages but falls behind in message-level organization, search effectiveness, and flexibility — the exact areas causing user frustration.
Competitive Advantages
- Integration with Microsoft 365 and third-party tools without redirecting to external sites
- Structured organization with Teams channels, more scalable than Slack's flat workspace model
- Rich email-like message formatting (headings, lists, code blocks, tables)
- @mention individuals, teams, or specific tags for targeted alerts
- Enterprise-level security and compliance built-in
Disadvantages
- Poor message organization in direct chats and group chats
- Limited saved messages functionality
- Only one pinned chat allowed — Slack offers multiple pinned messages
- Ineffective search unlike Slack's smarter, contextual search
- Difficult to archive, collapse, or organize old chat messages
- No message scheduling, no way to export chat messages
Anonymized Participant Overview
Six participants were recruited across two user types: 3 daily active Microsoft Teams users and 3 moderate users. 45-minute interviews were conducted between June 1–12, 2025.
Participant 1
Product Specialist
Daily Active User
Participant 2
Advanced Project Engineer
Daily Active User
Participant 3
Disease Intervention Specialist
Moderate User
Participant 4
Director of Mobile Services
Moderate User
Participant 5
Customer Support Specialist
Daily Active User
Participant 6
Sales Associate
Moderate User
06
Key Insights & Findings
What We Heard
Six high-level insights emerged from across the six participant interviews, consistently revealing organizational frustrations and workaround behaviors.
High Level Insights
Users rely heavily on direct messages for important communication
Manual note taking is a dominant workaround due to lack of sufficient organizational features
Pinned chats are helpful but extremely limited in functionality
Search is the most frustrating and ineffective feature across all users
Group chats create information overload and bury important messages
Users have creative ideas for improving organization and retrieval but lack native support
1
Users rely heavily on direct messages for important communication
Participants consistently return to direct messages with supervisors for updates and clarifications
Participant 2 has 6 pinned direct chats with mentors and reports, which he revisits frequently
Participant 4 prefers direct chats for a "safe space" to communicate with her immediate team
"I find it easier to just ask my manager the same question again rather than looking for it" — Participant 3
2
Manual note taking is a dominant workaround
Participant 3 keeps a running to-do list with short summaries and revisits chats for missing details
Participant 2 uses OneNote to log meeting minutes and organizes chat content manually
Participants 5 and 6 both rely on jotting down important client details and dates outside of Teams
"I use OneNote for manual note taking but I wish it could be incorporated into the Teams chat interface" — Participant 2
3
Pinned chats are helpful but extremely limited
Participants noted frustration with being able to pin only one message per chat
Participant 3 expressed desire for a "personal pinboard" or the ability to flag key messages
Participant 6 uses the pinned chat with her supervisor regularly but wishes individual messages could also be saved
"There is no point for this feature if you can only pin one message. I need to be able to pin several messages in a chat" — Participant 1
4
Search is the most frustrating and ineffective feature
Participant 1 needed 3 different keyword variations to find a certificate-related message
Participant 3 gave up searching and simply repeated questions due to poor results and no sorting options
Participants 4 said filters like date range and sender "do not work," calling the experience "crummy"
"I searched for the word 'exclusion' because I remember that word in my message but the search results were random and mixed up" — Participant 3
5
Group chats create information overload
Participant 3 finds group chats overwhelming, often missing updates in the flood of casual messages
Participant 4 pointed out the difficulty in finding urgent requests in noisy group threads
Participant 5 said there is "too much fluff to dig through" when trying to find important information
"I usually end up infinity scrolling to find messages in a group chat and it's extremely frustrating" — Participant 4
6
Users have creative ideas but lack native support
Participant 1 suggested tagging or categorizing messages at the time of sending
Participant 2 wants OneNote integration and a repository for chat files
Participant 5 envisions a collapsible sidebar or folder system to store and organize critical messages
Participant 4 wants exportable, taggable conversation folders and a way to sort chats by project or topic
Meet Elena Morris
Elena Morris is a composite persona representing the daily active Microsoft Teams user who emerged consistently from the research — a technically proficient professional who resorts to external workarounds due to Teams' organizational limitations.
Elena is a highly organized project engineer who manages multiple stakeholder communications across various direct messages, group chats, and team channels in Microsoft Teams. Teams is Elena's main tool for daily communication, project updates, and information sharing. Despite having a strong background in tech, she often creates her own workarounds — like manual note taking in OneNote and screenshots — to compensate for the lack of robust message organization and retrieval features in Teams.
Goals
- Retrieve important messages quickly without having to scroll or search excessively
- Streamline communication for active projects across multiple chats
- Reduce dependency on external tools like OneNote by having better in-app organization
- Maintain a clear and prioritized view of urgent and relevant conversations
Pain Points
- Search is ineffective and requires exact keywords, offers poor filtering, and lacks relevance
- Group chats are overwhelming — important messages are buried in long, casual threads
- Cannot pin or categorize individual messages, only whole chats
- Saved messages are hard to find and rarely used
- Constant manual workarounds like copying and pasting into notes or taking screenshots
Motivations
- Wants to be efficient and productive without wasting time hunting down messages
- Seeks clarity and control in communication, especially in important projects
- Prefers integrated, seamless tools over scattered workarounds
- Motivated by the idea of Teams being a "central hub" for work, not just a chat app
First Prototype: Exploring the Core Features
Based on research insights, Prototype V1 introduced four key features: improved pinned messages with multi-pin support, a message tagging system, an in-chat notes sidebar, and smarter search with filter options. The goal was to validate the core concepts before refining the interaction model.
📌 Pinned Message Panel — V1
📝 In-Chat Notes Sidebar — V1
09
Usability Testing — Round 1
Testing Prototype V1 With 6 Participants
All six original research participants were brought back to test Prototype V1. Each session was approximately 30 minutes and included three task scenarios: pinning messages, tagging and retrieving a message, and using the updated search and filter. Metrics were collected across time on task, error count, and post-session satisfaction.
58
Average SUS Score
Marginal usability
2.5
Avg. errors per task
Above acceptable threshold
74s
Avg. time on task
Across all 3 scenarios
67%
Task completion rate
Needed improvement
| Participant |
Task 1 — Pin Messages |
Task 2 — Tag & Retrieve |
Task 3 — Search & Filter |
Errors |
SUS Score |
Completion |
| P1 · Product Specialist |
52s |
68s |
91s |
3 |
55 |
Partial |
| P2 · Project Engineer |
41s |
55s |
72s |
1 |
72 |
Complete |
| P3 · Disease Intervention |
78s |
95s |
110s |
4 |
44 |
Incomplete |
| P4 · Director Mobile Svcs |
38s |
62s |
84s |
2 |
63 |
Complete |
| P5 · Customer Support |
61s |
79s |
102s |
3 |
51 |
Partial |
| P6 · Sales Associate |
55s |
70s |
88s |
2 |
63 |
Complete |
| Average |
54s |
72s |
91s |
2.5 |
58 |
67% Complete |
Pinning felt hidden
4 of 6 participants struggled to discover the multi-pin feature. The interaction was buried in a right-click context menu with no visual affordance in the chat header — users expected a visible toolbar button.
Tags lacked visual feedback
Participants were unsure if a tag had been applied. Missing confirmation states and no color differentiation between tag types made the tagging flow feel unresponsive.
Search still felt incomplete
Participants expected to filter by tag within search results. The disconnect between the tagging system and search was a consistent frustration point across P1, P3, and P5.
Notes sidebar was well received
All 6 participants responded positively to in-chat notes. P2 said it would eliminate his need for OneNote during meetings — a clear strength to build on in V2.
Second Prototype: Addressing the Test Feedback
V2 directly addressed every major pain point surfaced in the V1 usability test. Pinning was surfaced in the chat toolbar for immediate discoverability. Tags gained color-coded confirmations and became searchable. The notes sidebar received persistent state and a cleaner editing experience. Search filters were expanded and unified with the tag system.
🔍 Pinned Message Search — V2
📝 In-Chat Notes Sidebar — V2
Key Changes V1 → V2
What Changed and Why
↑
Pin affordance moved to toolbar — A pin icon was added directly to the chat header, resolving the discoverability issue. 5 of 6 participants found it immediately in re-testing vs. 2 of 6 in V1.
↑
Pinned messages now searchable — V2 introduced a dedicated search within the pinned messages panel, allowing users to filter pinned content by keyword — one of the top user challenges from testing.
↑
Color-coded tag confirmation — Tags now appear as a colored chip immediately on application, providing clear visual feedback. The tagging error rate dropped from an average of 2.5 errors per task in V1 to 0.7 in V2.
↑
Persistent notes sidebar with autosave — Notes now autosave per conversation with a richer editing experience. Participants rated the notes feature 4.6/5 avg. in V2 re-testing, up from 3.8/5 in V1.
Takeaways to Guide Design
Six research-backed design recommendations emerged from the synthesis process — each directly tied to participant pain points and creative suggestions surfaced during interviews.
1
Quick Access Over Complexity
Prioritize accessibility and visibility for existing features such as pinned chats and saved messages. Bring attention to these features within a chat or include a dedicated and always-visible side panel for quick access.
2
Message-Level Tools, Not Just Chat-Level Tools
Allow users to pin, tag, and/or categorize individual messages within a chat. Allow these messages to be organized in a side panel within a chat for quick retrieval of information.
3
Improved Search Functionality
Improve search by allowing users to recall fragments of a message and not the exact phrase. Expand to more filters such as date, user, and message type, as well as expand sort results to include relevance, most recent, or source.
4
Information Hierarchy Is Lacking Across Chats
In group chats specifically, allow users to prioritize messages by using labels such as "High Priority" or "Team Update." Allow users to pin several messages in a chat or the ability to highlight specific messages to ensure those are visible to the entire team.
5
Improved Feature Discoverability
Make features more discoverable by including onboarding steps, tooltips, or prompts in the chat UI. For example, "Save This?" would display in a popup if a user copied a message in a chat.
6
Manual Workarounds Reveal Design Gaps
Support in-app note taking with integrations to third-party tools such as OneNote or a new UI note-taking feature in the sidebar, directly addressing the #1 compensatory behavior observed across participants.
What This Research Revealed
These findings reinforce that while Teams offers basic communication functionality, it lacks the depth, flexibility, and intuitiveness needed by daily users who must organize and retrieve information efficiently.
01
Microsoft Teams Lacks Intuitive Organizational Tools
Users struggle to manage and retrieve important information efficiently. Current tools like pinned chats, saved messages, and search lack flexibility and depth, leading to frustration and workarounds like manual note-taking or using external apps like OneNote.
02
Search Functionality Is a Major Pain Point Across Users
Every participant voiced frustration with the search feature in Teams, citing irrelevant results and poor filtering. This leads to reduced productivity — some users opt to ask questions again rather than digging through old chat message threads.
03
Users Are Creating Their Own Workarounds
Users consistently rely on manual workarounds like note-taking, logging messages in notes, or taking screenshots to avoid endless scrolling. This behavior shows that users have clear mental models for how they want to organize chats — an opportunity for design solutions that align with user needs.