I recall a world-class nay-sayer.
If being negative were an Olympic event, this person would be a decathlon champion. Pessimists and cynics would carry him on their shoulders to the cheers of crowds shouting, "Nope. Impossible. We tried that before."
He could readily tell you 25 reasons why a task could not be performed but seldom, unless heavy pressure was applied, would disclose how it could be done and even then you would have to ask just the right question.
In short, he was maddening.
Not that his observations didn't have merit. They often did. But his constant refrain of negativism only triggered the understandable question of whether he had any interest in our success. Although the rest of us might not be so sophisticated in our reasoning, we could easily come up with a quick list of why something might not work. Unlike the nay-sayer, however, we knew that our job was to make things happen. It was entirely reasonable to wonder why he should be kept around.
The nay-sayer had another characteristic that was especially frustrating: He appeared to take a certain amount of enjoyment in shooting down the proposals of others. Although he usually went through the motions of "regretfully" informing us of the downsides, you could see in his eyes the sparkle of a man who has found his calling: dream stomping.
That predictability became his downfall. After a while, his credibility suffered. Several of the projects he'd drenched in cold water turned out to be unquestionable successes. Like The Little Boy Who Cried Wolf, the nay-sayer was ignored.
As in that sad tale, it was possible that some day one of his dire predictions would come true. By then, however, the victims of his earlier negativity didn't care.
They were rooting for the wolf.