I think the thing that I learned from him the most was the power of prototyping. And that even though he was such a great product thinker, he would always say, 'I can't tell you if this is going to work. I have to feel it. I have to try it. And a mock-up doesn't tell you what it's going to feel like.'
Feel it before you build it
Discovery → Design Thinking
How does this feel? Is something we talk more about at work than pretty much anything else, which is like, how does this screen feel? How does this flow feel? How does this feature feel?
The faster you can find out if you're on the right track, the more quickly you can learn and you can course correct and ultimately you can get to a better place faster than if you spent months working on that prototype.
You should wait as long as possible to draw a picture. Once you make that mark on the canvas, everything you do after that is in response to that mark.
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