Project Type
Challenges — find it, track it, check in
Role
Product Design, Strategy
Platform
iOS, Apple Watch
Team
1 Designer, 1 Engineer, 1 Pm
Timeline
8 weeks
Challenges — find it, track it, check in
Project Overview
Challenges is an app that supports group activities like mindful eating and Fruit & Veggie log in. We provide Challenges app to Apple, whose employees are the primary users. Apple has used Challenges for internal programs for about 10 years, making it a key stakeholder with high expectations for quality and refinement.
After ten years, the app was outdated and needed a redesign. We also updated the mindful eating challenge and rebuilt the Apple Watch experience, since many users access Challenges from their wrist.
Our goal was to help users quickly find challenges, track progress, and take action without interface friction, so they could move from selection to check-in with less effort. On the Watch, this meant redesigning the starting point so users with multiple active challenges would not need hidden gestures to access them.
I joined the project midway, after the initial direction was set. I built on this foundation and led the remaining UX and visual design through launch. Extending another designer’s direction required understanding the rationale behind earlier decisions to ensure a seamless continuation. I collaborated closely with engineers to ensure our design intent translated smoothly into implementation, and shared regular design updates with our product manager to align on priorities and timing.
On iPhone, I was responsible for sign-up, sign-in, password recovery, the landing screen and its Lottie animation, progress indicators, leaderboards, summary cards, and featured challenges. I led the full Watch redesign, including navigation, hierarchy, and check-in flows. I also developed a concise design system for typography, colors, and cards across both platforms using native components.
Project Overview
Challenges is an app that supports group activities like mindful eating and Fruit & Veggie log in. We provide Challenges app to Apple, whose employees are the primary users. Apple has used Challenges for internal programs for about 10 years, making it a key stakeholder with high expectations for quality and refinement.
After ten years, the app was outdated and needed a redesign. We also updated the mindful eating challenge and rebuilt the Apple Watch experience, since many users access Challenges from their wrist.
Our goal was to help users quickly find challenges, track progress, and take action without interface friction, so they could move from selection to check-in with less effort. On the Watch, this meant redesigning the starting point so users with multiple active challenges would not need hidden gestures to access them.
I joined the project midway, after the initial direction was set. I built on this foundation and led the remaining UX and visual design through launch. Extending another designer’s direction required understanding the rationale behind earlier decisions to ensure a seamless continuation. I collaborated closely with engineers to ensure our design intent translated smoothly into implementation, and shared regular design updates with our product manager to align on priorities and timing.
On iPhone, I was responsible for sign-up, sign-in, password recovery, the landing screen and its Lottie animation, progress indicators, leaderboards, summary cards, and featured challenges. I led the full Watch redesign, including navigation, hierarchy, and check-in flows. I also developed a concise design system for typography, colors, and cards across both platforms using native components.
The Problem
After 10 years, the app had become less effective. Progress was difficult to read, the leaderboard was cluttered, and on the Watch, finding and checking into challenges required too much effort. With Liquid Glass approaching, it was the right time to address the underlying structure, not just the appearance.
These were the questions behind it:
Why was progress hard to read? Different challenges track different activities, but the compact indicators did not reflect that. The small version felt disconnected from the challenge view.
Why did the leaderboard feel noisy? The same labels repeated across team and individual points and rankings, so the words competed with the numbers people wanted to compare.
Why was the Watch the biggest problem? Everything inside a challenge was crammed into one continuous scroll. Multiple challenges also lived on horizontal pages that only existed if you happened to discover a sideways swipe.
Why now? The Liquid Glass modernization opened the door to fix navigation and hierarchy at the same time, instead of treating the refresh as skin deep.
The Problem
After 10 years, the app had become less effective. Progress was difficult to read, the leaderboard was cluttered, and on the Watch, finding and checking into challenges required too much effort. With Liquid Glass approaching, it was the right time to address the underlying structure, not just the appearance.
These were the questions behind it:
Why was progress hard to read? Different challenges track different activities, but the compact indicators did not reflect that. The small version felt disconnected from the challenge view.
Why did the leaderboard feel noisy? The same labels repeated across team and individual points and rankings, so the words competed with the numbers people wanted to compare.
Why was the Watch the biggest problem? Everything inside a challenge was crammed into one continuous scroll. Multiple challenges also lived on horizontal pages that only existed if you happened to discover a sideways swipe.
Why now? The Liquid Glass modernization opened the door to fix navigation and hierarchy at the same time, instead of treating the refresh as skin deep.
The Messy Middle
I joined the project midway, with some decisions already made, others still open, and some areas not yet started. The scope included multiple pages and interactions progressing simultaneously, so the process needed to be efficient. That meant I had to orient quickly before moving into design decisions.
First, I familiarized myself with the prior decisions, and the intent behind them.
Next, I prioritized issues and pages, addressing the most critical items first. From there, I moved into the remaining phone flows.
Simplify the remaining phone flows: sign-up and sign-in, the landing screen, progress indicators, leaderboards, and summary cards.
I reimagined the Watch experience, exploring navigation and hierarchy from the ground up, as the previous structure caused significant friction.
I applied native components and shared styles, keeping the design system intentionally minimal with a focused set of type, colors, and cards rather than over-building for a targeted app.
Refine with feedback, then ship. I worked through feedback from our design director and Apple, following Apple’s guidance on navigation titles, back actions, and close actions. Keep information comparable. Use native components wherever possible. Carry familiar progress patterns between phone and Watch.
This project predates AI in our workflow, so it relied on research, exploration, and hands-on iteration.
The Messy Middle
I joined the project midway, with some decisions already made, others still open, and some areas not yet started. The scope included multiple pages and interactions progressing simultaneously, so the process needed to be efficient. That meant I had to orient quickly before moving into design decisions.
First, I familiarized myself with the prior decisions, and the intent behind them.
Next, I prioritized issues and pages, addressing the most critical items first. From there, I moved into the remaining phone flows.
Simplify the remaining phone flows: sign-up and sign-in, the landing screen, progress indicators, leaderboards, and summary cards.
I reimagined the Watch experience, exploring navigation and hierarchy from the ground up, as the previous structure caused significant friction.
I applied native components and shared styles, keeping the design system intentionally minimal with a focused set of type, colors, and cards rather than over-building for a targeted app.
Refine with feedback, then ship. I worked through feedback from our design director and Apple, following Apple’s guidance on navigation titles, back actions, and close actions. Keep information comparable. Use native components wherever possible. Carry familiar progress patterns between phone and Watch.
This project predates AI in our workflow, so it relied on research, exploration, and hands-on iteration.
Top 3 Design Decisions
Decision 1
How do people find a challenge they can’t see?
The problem: On the Watch, multiple challenges were placed on horizontal pages. If users did not know to swipe sideways, they were unaware of other available challenges. That made discovery depend on a gesture people might miss.
What I did: I added a challenge list at the start, allowing users to select a challenge before entering its pages.
How it solved it: All active challenges are now visible upfront, so discovery no longer depends on a hidden gesture and users can choose sooner.
The tradeoff: This approach adds a step before viewing details, but making choices visible is preferable to users missing available challenges.
Decision 1
How do people find a challenge they can’t see?
The problem: On the Watch, multiple challenges were placed on horizontal pages. If users did not know to swipe sideways, they were unaware of other available challenges. That made discovery depend on a gesture people might miss.
What I did: I added a challenge list at the start, allowing users to select a challenge before entering its pages.
How it solved it: All active challenges are now visible upfront, so discovery no longer depends on a hidden gesture and users can choose sooner.
The tradeoff: This approach adds a step before viewing details, but making choices visible is preferable to users missing available challenges.
Decision 2
How do you make a leaderboard about the numbers, not the labels?
The problem: During review, our design director noted the leaderboard was repetitive, with the same labels on every card competing with the values users wanted to compare. That feedback showed the layout needed a clearer structure.
What I did: I reorganized information into rows and columns, allowing the structure to convey meaning without repeated labels. I also redesigned the summary card to make different point types easier to read at a glance.
The tradeoff: Each row now relies on column headers rather than being self-explanatory. However, using structure instead of repeated words made the numbers easier to compare at a glance.
Decision 2
How do you make a leaderboard about the numbers, not the labels?
The problem: During review, our design director noted the leaderboard was repetitive, with the same labels on every card competing with the values users wanted to compare. That feedback showed the layout needed a clearer structure.
What I did: I reorganized information into rows and columns, allowing the structure to convey meaning without repeated labels. I also redesigned the summary card to make different point types easier to read at a glance.
The tradeoff: Each row now relies on column headers rather than being self-explanatory. However, using structure instead of repeated words made the numbers easier to compare at a glance.
Decision 3
How do you make something less prominent without making it harder to choose?
The problem: Apple requested that featured challenges be less prominent. However, with four challenges having similar names, reducing their visibility risked making them difficult to distinguish. That created a tension between hierarchy and clarity.
What I did: I placed them in a dropdown to respect the requested hierarchy and created distinct imagery for each, starting from SF Symbols, so they are easy to distinguish when expanded.
How it solved it: Collapsed, it honors Apple’s request. Expanded, the choices remain clear and easy to tell apart.
The tradeoff: Featured challenges have less visibility by default. This approach satisfies a key stakeholder while maintaining clarity when the dropdown is opened.
Decision 3
How do you make something less prominent without making it harder to choose?
The problem: Apple requested that featured challenges be less prominent. However, with four challenges having similar names, reducing their visibility risked making them difficult to distinguish. That created a tension between hierarchy and clarity.
What I did: I placed them in a dropdown to respect the requested hierarchy and created distinct imagery for each, starting from SF Symbols, so they are easy to distinguish when expanded.
How it solved it: Collapsed, it honors Apple’s request. Expanded, the choices remain clear and easy to tell apart.
The tradeoff: Featured challenges have less visibility by default. This approach satisfies a key stakeholder while maintaining clarity when the dropdown is opened.
The Challeges
Joining the project mid-development required quickly learning a new product, understanding previous decisions, and making new ones simultaneously. That made the early phase especially demanding.
Designing a new Apple Watch experience involved making numerous decisions for a small screen, with limited existing patterns to reference.
Ensuring alignment with Liquid Glass required matching Apple’s new design language, which was especially important given Apple’s role as the primary customer.
The Challeges
Joining the project mid-development required quickly learning a new product, understanding previous decisions, and making new ones simultaneously. That made the early phase especially demanding.
Designing a new Apple Watch experience involved making numerous decisions for a small screen, with limited existing patterns to reference.
Ensuring alignment with Liquid Glass required matching Apple’s new design language, which was especially important given Apple’s role as the primary customer.
The Outcome
The redesign launched on iPhone and Apple Watch. Apple’s feedback was positive, based on what was shared with me. Early responses included comments like, “This makes it much easier to see my active challenges on the Watch.” Preliminary usage data suggests that users are now able to find and select challenges about 25% faster on the Watch compared to the previous version. Measured outcomes for check-in completion and ease of use are still being collected, so gathering more evidence on user impact is the next step.
The Outcome
The redesign launched on iPhone and Apple Watch. Apple’s feedback was positive, based on what was shared with me. Early responses included comments like, “This makes it much easier to see my active challenges on the Watch.” Preliminary usage data suggests that users are now able to find and select challenges about 25% faster on the Watch compared to the previous version. Measured outcomes for check-in completion and ease of use are still being collected, so gathering more evidence on user impact is the next step.
My Reflection
Effectively building on another designer’s direction is a valuable skill. The goal was not to override or preserve the foundation unchanged, but to understand it thoroughly and extend it into a coherent product. The Watch experience reinforced that clarity on small screens comes from defining the purpose of each view.
If I continued, I would test the new Watch navigation against the previous version with real users to validate the improvement in discoverability. I would set up a usability study with participants drawn from our key user groups, giving them common tasks on both versions and timing how quickly they can find and join a challenge. I would also measure task completion rates and ask users to rate the clarity of navigation. This would provide clear, actionable evidence for further iteration.
My Reflection
Effectively building on another designer’s direction is a valuable skill. The goal was not to override or preserve the foundation unchanged, but to understand it thoroughly and extend it into a coherent product. The Watch experience reinforced that clarity on small screens comes from defining the purpose of each view.
If I continued, I would test the new Watch navigation against the previous version with real users to validate the improvement in discoverability. I would set up a usability study with participants drawn from our key user groups, giving them common tasks on both versions and timing how quickly they can find and join a challenge. I would also measure task completion rates and ask users to rate the clarity of navigation. This would provide clear, actionable evidence for further iteration.
