Early and plain beats late and padded
The instinct is to soften bad news with a long lead-up, but a long lead-up usually just makes people brace for something worse than it is. Plain and early is kinder than late and cushioned.
Flag it before it becomes a surprise
“I want to flag something early: we are going to miss Friday.” Saying it as soon as you know, rather than waiting for the deadline to arrive, keeps you managing the news instead of explaining a miss after the fact.
Pair the news with the next move
“The short version is this did not work, here is what we are doing next.” Bad news without a next step reads as a dead end. The same news with a next step reads as someone still in control of the situation.