A decade after acquiring Gatorade’s parent company and turning that brand into every athlete’s must-have energy drink, Quaker CEO William Smithburg moved in on another drink surging in popularity: Snapple.

Despite a $1.8 billion bid and a lot of unanswered questions, Smithburg received the full support of his board of directors. Three brutal years later, Snapple was sold for $300,000 and Smithburg stepped down.

“We should have had a couple of people arguing the ‘no’ side of the evaluation,” he said.

Organizations often suffer when devil’s advocacy is in short supply, Chip and Dan Heath illustrate in “Decisive: How to Make Better Choices in Life and Work.”

Credit unions benefit from a board of directors that constructively challenges conventional thinking, investigates additional options, and combats hubris and the tug of short-term emotions.

“We want to avoid the momentary discomfort of being challenged, which is understandable, but surely it’s preferable to the pain of walking blindly into a bad decision,” the authors write.

Some organizations license skepticism by appointing individuals to the task. The best approach is to encourage the entire board to participate in what the authors characterize as “values-based opposition”—avoiding adversarial politics by disagreeing without being disagreeable—and to work as collaborators and analyze options objectively.

Become a better devil’s advocate by following these guidelines, the authors advise: