Clockwise’s automated calendar optimization was powerful, but invisible. Users couldn’t see what it did or why, which made it hard to trust and even harder to adopt. While our 4pm defrag worked like a Roomba for the automation-comfortable, we were leaving behind a much bigger segment: people who wanted control, visibility, and validation.

The Opportunity
I led design on Plan My Week (PMW), a manual optimization tool that let users preview, understand, and approve suggested meeting moves. The goal was twofold:

• Fix the UX gap by making automation transparent and trustworthy

• Unlock growth by serving new, automation-hesitant users

We treated this not as a feature, but as a strategic bet: if we could show our work, we could expand our addressable market.

What We Built
I ran three iterative testing rounds, refining the interface and narrative to balance clarity with delight. I also began contributing to the frontend codebase to support polish and reduce load on engineers.

• Trigger-based optimization: Users initiate optimization manually and preview changes before committing

• Thoughtful motion: Slowed-down animations built trust by signaling deliberateness

• Calendar score: Inspired by fitness and sleep apps, it gave users an emotional anchor to evaluate changes

• Suggestion cards: Explained each improvement by value type—conflict resolution, focus time, or preference alignment

• Contextual feedback: A TL;DR summary clarified why users saw small or big gains, addressing attribution confusion

Impact
Users described PMW as “Clockwise working with me, not around me.” It is quickly becoming a trusted entry point for new users and a teaching tool for the value of our automation. It introduced frameworks we now use across the product:

• Transparency as trust infrastructure

• Motion as mental model communication 

• Emotional anchoring in complex systems

PMW also became central to onboarding and reduced time-to-value for a broad range of users… especially those who needed to see the benefit before trusting automation.