We just released a fresh new view of the sidebar in the Checkly app. This decision was made after some extensive user research—and this is the story of how we got to the final solution.
How It Started
Once upon a time, during a team meeting and live demo session, a designer noticed something odd: whenever her teammates needed to open a specific page in the app, they did this:
Instead of going directly to the correct page, they would click through the sidebar icons one by one until they landed on the right one. This wasn’t just an internal thing—during customer interviews, the same behavior showed up. People would screen share and instinctively cycle through icons to navigate the app.
But navigation isn’t supposed to be a guessing game. It should be intuitive and efficient—two things our sidebar clearly wasn’t delivering.
So, what went wrong?
The reasons are historical—growing organically means adding new things into app pockets without thinking ahead about how deep the pockets should be. We had to pause to rethink the structure as it grew. Eventually, the mental effort of figuring out what to click became higher than just clicking everything at random.
That’s when we knew: It was time to rethink our sidebar.
The Solution
We identified two main issues behind this “random-click” behavior:
1. Icons Without Labels
Most of the time, the sidebar stayed in its collapsed state—just a column of icons. Labels only appeared on hover, and let’s face it: icons without context don’t work. They confuse more than they help.
What we changed:
We redesigned the sidebar to always show both icons and labels. The collapsed state still exists, but now it fully hides the sidebar to let users focus on content. When you hover, the full sidebar (with labels) slides back into view.
2. Poor Categorization
Our menu had grown too large and too random. We hit the cognitive limit described by The Magical Number Seven, Plus or Minus Two—meaning users couldn’t process all the items at once. It was time to break things into more manageable groups.
How we approached it:
We ran a card-sorting exercise internally to see how team members would group and label sidebar items.
Interestingly, despite some debate around category names and a few tricky items, there was strong consensus on most groupings.
Introducing the New Sidebar
We’re excited to roll out the updated sidebar—and we hope it makes your experience smoother and more enjoyable. No guessing games. Just clear, structured, thoughtful navigation.
As always, we’d love your feedback. Drop us a note in the community, use the support widget, or reach out through any channel that works for you.