Never preface bad news.
Everyone has to deliver the bad news occasionally. When you do, start with the worst part, keep it short, and never preface it with long explanations.
Pretty simple, right? But, we always went to preface the bad news with a, "sit down for a minute, I need to explain something that happened, that probably is not too good," type sentence, which gives the recipient 10 to 20 seconds to consider dozens of catastrophes waiting to befall him. Remember the war movies where two stoic looking military men are walking up a long driveway as mom watches from a kitchen window? She knows why they are coming but the 20 seconds it takes for them to get to the front door and deliver the news are the longest she will ever have. That's what it's like for the recipient when you ramble on about things before getting to the point.
I had some good news to give my wife the other day and I was "prefacing" away to the point where she finally interrupted and said, "Is the end good or bad?" I said "good" and continued with my too-long introduction. Don't do that with bad news.
Say it, then explain it. That way the recipient knows exactly what the subject is.
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