It is a turn from the bunny slope of the known, to the mogul hill of the unknown. The trick, then, is to create an environment where team members are comfortable making mistakes. They need a situation where they can begin to see mistakes for what they truly are - opportunities to learn. The reluctance to view mistakes in this way is obvious. We all have a very clear sense of what happens when we succeed.
Success leads to celebration.
At a recent meeting of the Registrar's Council at my university there was actually spontaneous applause when it was announced that a risky venture had succeeded. We are trained from an early age that success is what gets us what we want. When we talk about our jobs, it is the successes we highlight. As a society we value product over process. We celebrate what we produce and not what we have learned along the way.