The billion-dollar mistake hiding in a simple checklist

Most product teams struggle with a dangerous form of blindness: the belief that data overrides intuition.

You see this happen even at the highest levels of tech. Let’s look at a specific, maddening example that many of you face daily. You use a tool to organize your life --let’s say, Google Tasks. You set a recurring task: “Submit Weekly Report,” due every Friday. It’s Friday morning, you finish the report, and you check the box with a sense of accomplishment.

But then, the task just disappears.

Logic (and basic human psychology) dictates that the task should immediately regenerate for next Friday. You want to see it. You want to plan for it. You want to add sub-notes to the next instance. But in the Google ecosystem, that next task doesn’t exist yet. It won’t appear until the clock strikes midnight on the due date.

This isn’t a bug. It’s a design choice. And it is a choice that fundamentally misunderstands how high-performers work. You aren’t just doing tasks; you are managing a workflow. When the tool hides the future from you, it cripples your ability to plan.

The biggest challenge facing modern product managers is not a lack of engineering talent; it’s a deafness to the actual workflow of the user. You rely on “Daily Active Users” metrics which look fine, while ignoring the core usability friction that drives your power users crazy.

The Sound of Screaming into the Void

Here is where the frustration turns into resentment.

This specific issue with Google Tasks ---the “hidden recurring task”--- isn’t new. People have been complaining about this on support forums, Reddit threads, and Twitter since 2019. That is six years of clear, articulate feedback from power users who want to love the product.

The worst part is the silence.

When you ignore a user’s core workflow friction for half a decade, you aren’t just being slow; you are being arrogant. Every day this continues, you send a clear message to your user base: “We know how you should work better than you do.”

This leads to a complete erosion of trust. It forces users ---people like me—to abandon an ecosystem we are otherwise deeply invested in. I moved to Todoist not because I wanted to pay for another subscription, but because I needed a tool that respected my need to see the future.

Think about your own product. Are your users asking for a feature that you’ve deprioritized because it doesn’t fit your “vision”? While you debate internal roadmaps, your users are feeling the daily pain of a thousand papercuts. Eventually, they stop complaining. They just leave. And they don’t come back.

The “Data-Driven” Trap

But here’s what most people don’t realize about why this happens.

It isn’t that Google PMs are lazy. They are likely some of the smartest, hardest-working people in the industry. The problem is a specific cognitive trap called “Metric Fixation.”

They are likely looking at data that shows “Task Completion Rates” are high. They see millions of users checking off boxes. The data says the product is working.

Wait, what’s missing?

The data doesn’t capture the sigh of frustration when a user has to create a manual duplicate task just to track next week’s agenda. The data doesn’t capture the anxiety of an empty list that should be full. It doesn’t capture the user who silently migrates to Todoist.

We are going to flip this dynamic. There is a way to prioritize features that doesn’t rely solely on cold, hard usage stats, but rather on “Workflow Velocity.”

Building for Flow

Imagine if your product actually anticipated your user’s next move.

Picture this: You complete a recurring task, and instantly, the next one slides into view at the bottom of your list, dated for next week. You feel a sense of continuity. You aren’t just reacting to today; you are proactively managing tomorrow.

What if you could build a product that users trust implicitly?

In this future, your users feel heard. When they spot a friction point, they report it, knowing that a human on the other side understands the nuance of why it matters. They become your evangelists. They tell their colleagues, “You have to use this tool, it just gets how we work.”

You move from being a utility provider to a partner in their success. You stop bleeding users to competitors like Todoist because you own the most valuable asset in the market: User Empathy.

The “Anti-Google” Framework

So, how do you ensure you aren’t making the same mistake as the giants?

You need to shift from building features to enabling workflows. Here is the 3-step framework to audit your product management style and ensure you are listening to the right signals.

1. The “Dogfood” Audit
   You must use your product for real work. Not testing work—real work.
   The Google PM likely uses Tasks for simple grocery lists, not complex project management.
   ​Action: Force your team to use your product for a critical business function for one week. If it breaks their flow, it’s broken for the customer.
   ​
2. Measure “Time-to-Value” over “Engagement”
   Google sees high engagement (I keep opening the app to find my task). I see wasted time.
   ​
   Stop celebrating how long people spend in your app.
   Start measuring how quickly they achieve their specific outcome.
   ​Action: Identify the “Success Moment” (e.g., planning next week). If the UI blocks this, treat it as a P0 bug, even if the code is working “as designed.”
   ​
3. The “Legacy Complaint” Review
   Ignore the new feature requests for a moment. Look at your backlog.
   Find the tickets or complaints that are over 12 months old. If a complaint has persisted for years (like the 2019 Google Tasks thread), it is not a minor annoyance; it is a structural failure.
   ​Action: Dedicate one sprint per quarter purely to “Quality of Life” fixes based on the oldest, highest-volume user feedback.

The Lesson: I stick with Todoist because they solved the recurring task logic years ago. They listened. Google didn’t. Don’t be Google.