As a leader, I think the hardest situation to discern is when to let someone fail and when to let them flail.
Failing can teach lots of lessons. As can flailing.
You never want your organization to fail (as a whole). But flailing can produce resilience. And strength. It can make you better as you develop institutional memory to draw upon the next time things get tough.
The trick is to be able to tell when a team member is failing and when she’s flailing. Same for your company or club.
Failing means there is no tomorrow. Flailing means you’ll live to fight another day. Be sure to always take stock. If you can see the sunrise, keep flailing because you’ll get another shot and be better for it.
But if all you see is darkness, then failure is imminent. The only course then is to fight like hell in order to turn failure into flailure.