When do failures of execution become failures of intent?

My Grandpa Jake was a sage.

He was an anchor in a turbulent world.

In the context of my family, you can start a sentence with "Grandpa Jake once said..." and family will stop what they are doing and listen.

Grandpa Jake once said "failures of execution" are more forgivable than "failures of intent"
This is not a radical thought.

As kids we learned that the consequences were less severe if we mumbled, "It was an accident." or "I was just kidding." or "I did not mean to."  Often, we were given the benefit of the doubt and all was good.  We restarted with a fresh slate.

In a court of law, a criminal who cannot express remorse is sentenced much more severely than a criminal who voices a credible apology.

"Failures of execution" are more forgivable because they are more likely to be fixed than "failures of intent."  Change is hard, hard but possible.  Change will not happen if the subject does not want to change.  The horse is not even in the starting box.

Insanity is doing the same thing over-and-over again and expecting a different outcome
How many times must the bully in third grade "stumble" and trip his victim before it becomes clear that it is not a failure of execution?

How many times must a glib, practiced criminal express remorse...before going out and committing yet another crime, before it is clear that he is intentionally committing crime?

How many times will we give people a mulligan simply because they unfurled the banner, "Insert Noble Cause Here".

Outcomes matter.