The Stockdale paradox is a fascinating thing, but to paraphrase it for a corporate project point of view:
While you’re going to hit your delivery in the end. Don’t get overexcited, don’t over promise and under deliver as it wears your team and the other people on the project out and dispirits them. This philosophy works most practically in those hard grinds or crisis situations when delivering complex projects as you’re working through multiple options for delivery.
Getting overexcited about each one of your sub deliveries on a project is mentally very tiring for both your team and your clients, and it leads to a culture of avoiding disappointment. So people who are attempting to fix something for you, if you overhype it and it then doesn’t work they don’t want to tell you. Whereas if you go “right!, we’re gonna get there in the end, This is just option one, let’s go for it.” If option one doesn’t work, then they’re willing to tell you because even though you maintain your positivity, you’re not getting over optimistic and putting additional pressure on people that they don’t need.
Oh, that’s easy, the optimists. Oh, they were the ones who said, ‘We’re going to be out by Christmas.’ And Christmas would come, and Christmas would go. Then they’d say, ‘We’re going to be out by Easter.’ And Easter would come, and Easter would go. And then Thanksgiving, and then it would be Christmas again. And they died of a broken heart. This is a very important lesson. You must never confuse faith that you will prevail in the end—which you can never afford to lose—with the discipline to confront the most brutal facts of your current reality, whatever they might be.
– James Stockdale on “which prisoners didn’t make it out of Vietnam”