Not all failures are the same. Here are five kinds, from frequency = good all the way to please-don't!
FAIL OFTEN: Ideas that challenge the status quo. Proposals. Brainstorms. Concepts that open doors.
FAIL FREQUENTLY: Prototypes. Spreadsheets. Sample ads and copy.
FAIL OCCASIONALLY: Working mockups. Playtesting sessions. Board meetings.
FAIL RARELY: Interactions with small groups of actual users and customers.
FAIL NEVER: Keeping promises to your constituents.
The thing is, in their rush to play it safe and then their urgency to salvage everything in the face of an emergency, most organizations do precisely the opposite. They throw their customers or their people under the bus ("we had no choice") but rarely take the pro-active steps necessary to fail quietly, and often, in private, in advance, when there's still time to make things better.
Better to have a difficult conversation now than a failed customer interaction later.