Wu Ying gulped, realizing he was walking along the cliff’s edge of failure. Yet, perhaps the knowledge he was likely going to fail freed him. Knowing he would fail meant he had nothing to lose, and the fear of failure disappeared. There was no fear in certainty—just freedom.A thousand Li: The first stop by Tao Wong
One of the key factors in psychological safety is that it is ok to fail, and this is also a reason that agile has become so popular. It is a way to break big projects down in small chunks where it is ok to fail each part, but in the end, you have created something bigger.
I think one of the worst things you can end up in is the organization’s most important project that must not fail. Then the stress kicks in, the worry increases. And then flexibility, innovation and creativity disappear.
I have given some presentations around the analogy between skateboarding and working in an organization. When you practice skateboarding you fall a lot. More often you jump off the skateboard when you realise that a trick will not work. But you rarely hurt yourself. Because you know how to judge if something will not work, and you have practiced falling.
Good managers need to train themselves and their teams how to jump off when things are not going to plan and how to fall without hurting themselves and the organization.