Learning Environment

Mac Operating System Troubleshooting flowchartI recently read an article on MFA programs and was struck by the sentence “Teachers … must create an environment conducive to experimentation and to moving past self-censoring impulses.” [Is Happiness Possible in a Creative Writing Program?] This assertion seems to apply to managers as well as to teachers. I found myself asking, do I create such an environment when I design instruction?

One of my favorite projects to date is the Mac Operating System Troubleshooting computer-based training I designed. I specifically designed an environment that encouraged clicking all over the place. Who knows what delightful surprises you might find? There was no downside to clicking. Students were not punished for taking the course in whatever order they chose. They weren’t even punished for skipping content altogether. True, I couldn’t do too much about self-censoring impulses, except to present a visually delightful environment and to remove negative consequences for getting past that censor.

Most of my work lately has been for self-help. How does one create help such that users are comfortable experimenting and can get past that internal censor? Or is that the job of the product's user interface and flow, before the user even gets to in-product help? 

As a manager, teacher, parent, how do you encourage experimentation and getting past self-censorship?