I'm Patty, and I lead design for Planner in Yahoo Mail. I work closely with our AI team to turn inbox chaos into something that actually understands your day. If there's one thing this project has taught me about designing AI products, it's that empathy matters more than almost anything else.

Not all product failures show up in dashboards. Some show up as a single line in a feedback report, the kind that makes the room go quiet. And some failures don't come from a bad experiment. They come from never running the experiment at all.

This is a true story about one of those times, and what it took to catch it.

~Patty Wu
Principal Product Designer, Yahoo

Planner turns your Yahoo Mail inbox into a personal productivity hub. It automatically detects actionable items, like upcoming flights, dinner reservations, or package deliveries, and surfaces them when you need them. It's built to remember so you don't have to, which is exactly what made what happened next so hard to sit with.

She had a dog. Like most dog owners, she kept up with the small rituals of care: vet visits, grooming appointments that appeared in her Yahoo Mail inbox and were added to Planner without much thought.

Then her dog passed away.

A few days later, a reminder arrived: grooming appointment coming up. She tried to make it stop, but couldn't figure out how. The notifications kept coming, each one an unexpected knock at a door she was trying to close. She shared this experience with us: "I feel sad when Yahoo Mail reminds me of this...." And that was on us.

Gap 1: The toggle wasn't as obvious as we thought. After adding something to Planner, the interface shows "Added to Planner," and the idea was that tapping it again removes it. In practice, the label read like a confirmation, not an invitation to interact. The remove path existed, users just couldn't find it.

Gap 2: An edge case we hadn't designed for. Keeping email and Planner events independent was intentional, and usually right. But we'd never asked what happens when someone wants an event gone because the reason behind it no longer exists. For this user, that gap mattered.

One of our product principles at Yahoo Mail is "Be Data Informed and Context Driven." In hindsight, we were data informed, just not context driven enough.

We believed the AI would accurately detect what mattered, so a low removal rate felt like a solid success metric. It confirmed exactly what we hoped: it was working. That felt good, maybe too good. Looking back, it was confirmation bias. We never stopped to ask whether users weren't removing things because the AI was accurate, or because they couldn't find how. We were measuring the action, not the struggle behind it. Instead of revealing friction, the data masked it.

One user shared the story of her loss with us, and it reframed everything.

The static label is becoming an interactive "Go to Planner" button, with Remove moved into the Edit panel. Longer term, deleting an email will prompt: keep this event, or remove it too? No assumptions. The user decides.

And we're treating this rollout the way we should have treated the first one: as a hypothesis, not a launch. Each change comes with a specific question attached, not just "did removal go up," but "did it go up because people can finally do what they wanted, or because we're prompting them into it." We're building in the qualitative check up front this time, instead of hoping we'll stumble onto it later.

The best reminder is one that remains only as long as a user wants it. The best design ensures that when you want something gone, it goes.

This user's story changed how the team thinks about success metrics. Low removal rates used to feel like a green light. Now we ask whether users aren't removing things because they don't need to, or because they can't figure out how. It's a small shift in framing, but it opens up a completely different set of design problems.

For anyone building productivity features: don't just measure the action. Measure the struggle behind it. The absence of a negative signal is not the same as a positive experience.

The Planner design team at Yahoo Mail (Patty Wu, Michael Takeshita, Jennifer Ballesteros, and Edu Talavera) works closely with PM Shivani Tangri, alongside engineering, data science, and marketing, under the leadership of GM Kyle Miller. Special thanks to UX Researcher Stephanie Yang, whose research made this story possible, and to Community Manager Marilyn Jaynes for sharing this story with us. Planner is available in Yahoo Mail on iOS and Android.

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