Intuition is a weird thing. Its stuff you know, but don’t know you know. Ya know?
I often rely on intuition in my work here as a designer. Past experience plays a lot into this type of work. Building from that intuition takes hours of studying, experimenting, and… playing. This playtime allows you to deeply understand why some patterns work, and some patterns don’t. Like any skill, it gets easier the more you do it. but sometimes you need to recalibrate your intuition. 
I recently helped design the help button on WordPress.com along with a team of talented designers and developers. Early on in the project I spent some time exploring a handful of concepts, one of which kept the help button in the left-hand sidebar and very subdued.
It looked cool, but I knew intuitively that lots of people would have a tough time using this interface. The combination of subtle colors, excessive motion, and issues with the persistence of the sidebar led us down a different path.
The popover concept ended up being a better direction; It’s a more consistent pattern thats used elsewhere, and opens the door to more robust interactions and information. To alleviate the issue of the sidebar’s persistence (sometimes its not there, or on the other side… I know, right?) we moved the help button to the bottom right of (juuuust about) every screen.
All of the decisions we made came from trial and error using rapid-prototyping and our intuition. However, intuition gets stale. Or, maybe there’s just a piece missing or hidden.
Intuition is grounded in interpretation through iteration.
— Automattic Design Principle
As a member of the dotCom Design team here at Automattic, we recently wrapped up a research session talking with small business owners. We spoke with, listened to, and learned from a group of people not at all like ourselves. We discusses how these people started their business (or, how they planned to start their soon-to-be business), where the planned (or if they planned) to grow, and the tools they use to run their business.
I walked away a with a better understanding of a whole different segment of customers, and a larger, more robust intuition to use as I build and improve upon WordPress. It also built my confidence with some existing intuition—a lot of people we spoke with mentioned wanting someone to help them, or the ability to quickly help themselves. The new help button has opened the door to some other improvements: We’ve made it easier to start a new chat with a Happiness Engineer from the help button; The help popover shows topics based on the current screen your viewing; We’re incorporating more detailed help in both text and video formats to ensure we can help anyone regardless of their learning style.
Automattic Design 