In one of my favorite leadership books, Jim Collins in Good to Great, talks about a key distinction between good and great leaders. He named it the Stockdale Paradox after Admiral Jim Stockdale. Admiral Stockdale was the highest ranking United States military officer in the “Hanoi Hilton” prisoner-of-war camp during the height of the Vietnam War. Tortured over 20 times during his eight-year imprisonment from 1965 to 1973, Stockdale lived out the war without any prisoner’s rights, no set release date, and no certainty as to whether he would even survive to see his family again. He shouldered the burden of command; doing everything he could to create conditions that would increase the number of prisoners who would survive unbroken, while fighting an internal war against his captors and their attempts to use the prisoners for propaganda. At one point, he beat himself with a stool and cut himself with a razor, deliberately disfiguring himself, so that he could not be put on videotape as an example of a “well-treated prisoner.”

After his release, Stockdale became the first three-star officer in the history of the navy to wear both aviator wings and the Congressional Medal of Honour.

Collins tells the story of meeting Stockdale, “In preparation, I read In Love and War, the book Stockdale and his wife had written in alternating chapters, chronicling their experiences during those eight years.

As I moved through the book, I found myself getting depressed. It just seemed so bleak—the uncertainty of his fate, the brutality of his captors, and so forth. And then, it dawned on me: “Here I am sitting in my warm and comfortable office, looking out over the beautiful Stanford campus on a beautiful Saturday afternoon. I’m getting depressed reading this, and I know the end of the story! I know that he gets out, reunites with his family, becomes a national hero, and gets to spend the later years of his life studying philosophy on this same beautiful campus. If it feels depressing for me, how on earth did he deal with it when he was actually there and did not know the end of the story?”

“I never lost faith in the end of the story,” he said, when I asked him. “I never doubted not only that I would get out, but also that I would prevail in the end and turn the experience into the defining event of my life, which, in retrospect, I would not trade.”

I didn’t say anything for many minutes, and we continued the slow walk toward the faculty club, Stockdale limping and arc-swinging his stiff leg that had never fully recovered from repeated torture. Finally, after about a hundred meters of silence, I asked, “Who didn’t make it out?”

“Oh, that’s easy,” he said. “The optimists.”

“The optimists? I don’t understand,” I said, now completely confused, given what he’d said a hundred meters earlier.

“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.”

Another long pause, and more walking. Then he turned to me and said, “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.”

The Stockdale Paradox =

You must retain faith that you will prevail in the end, regardless of the difficulties.

AND at the same time…

You must confront the most brutal facts of your current reality, whatever they might be.

For me, the Stockdale Paradox carries an important lesson in leadership development, a lesson in faith and honesty: Never doubt that you can achieve your goals, no matter how lofty they may be and no matter how many critics and naysayers you may have. But at the same time, always take honest stock of your current situation. Don’t lie to yourself for fear of short-term embarrassment or discomfort, because such deception will only come back to defeat you in the end.

Living the first half of this paradox is relatively easy for some. They naturally optimists, looking for the opportunities in situations, and are solution-finders. Optimism is often held up as the epitome of leadership characteristics.

But optimism on its own can be a dangerous thing:

There’s no difference between a pessimist who says, “Oh, it’s hopeless, so don’t bother doing anything,” and an optimist who says, “Don’t bother doing anything, it’s going to turn out fine anyway.” Either way, nothing happens. – Yvon Chouinard.

So you need to embrace the second half of the Stockdale Paradox to really make strides. You must combine that optimism with brutal honesty and a willingness to take action.

Now of course, nobody likes admitting that they’re struggling to complete a project, or that they’ve chosen the wrong career or that they are overwhelmed. But admitting such truths is an absolute necessity if you want to grow and improve. It might feel like you’re taking a few steps backward by doing so, but you can view that retreat as the pull-back on a sling shot: you’re just setting yourself up to make significant progress down the road.

Some people are ‘natural’ pessimists.

The truth is, we can over do either of these ways of seeing and interacting with the world. Our ‘strength’ can become a weakness.

I meet leaders who are brilliant at diagnosing technical issues in their field of expertise; they can see all of the obstacles between them and their goals. This is a strength; overdone however, they come across as negative and demotivating. They think they are simply being realistic. As Stockdale says, we need to confront the brutal facts, however in ways that don’t make us or others feel defeated and overwhelmed at the beginning.

I also meet many leaders who are brilliant at reframing really difficult, overwhelming issues into opportunities. Many times this approach rallies the troops to put in an extra effort to succeed. However, use this approach too many times, an optimist can be unprepared and blindsided. This ultimately will reduce our trust in our leaders ability and make them seem naïve.

How to keep a balance between optimistic will to overcome and confronting the brutal facts?


  1. Investigate the realities of the challenges that you face. The first step is to make sure that you have as much information, from as many sources as possible. A plan to overcome the challenges needs to be based on facts, but also gathers information from other sources like – experience, hunches and ascertaining patterns. Ensure that there is nothing you are choosing not to see.
  2. Acknowledge the challenges to yourself and others without setting a tone of doom and gloom. This step is about being authentic and is crucial to gain trust. When we see the facts, especially when they seem particularly difficulty, there are two reactions. One temptation is to ignore them and be a bit ‘Polly-Anna’ and the other is to become fatalistic about the possible outcome. The trick seems to be to state the challenges without emotional hyperbole. Stating things calmly, using measured language is important to display an air of confidence and reduce anxiety.
  3. Reframe the challenge as an opportunity to shine without being flippant. This step provides the link between pessimism and optimism. Being able to reframe realities into a narrative, which provides hope and galvanises effort is critical.  Reframing is essentially about being able to see the positives and the choices within a situation.
  4. Determine to do whatever it takes to succeed. Let this step propel you into solutions and innovation. Most successes won’t happen through individual effort alone, ensure this step helps develop unity and collaboration amongst you team. The will to succeed often propels people to push themselves to find new answers and tap into their creative genius.
  5. Celebrate when you succeed. Never lose an opportunity to celebrate. Celebration honors people’s effort but also solidifies the team’s confidence to meet and overcome the next challenge. Confidence comes from seeing, meeting and then overcoming big challenges.

Which of these steps do you find most challenging?



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