Seeing the world as it is

Leadership lessons from Admiral James Stockdale

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You must never confuse faith that you will prevail in the end with the discipline to confront the most brutal facts of your current reality.

James Stockdale

The first time I heard of Vice Admiral James Stockdale I was an 18 year old Marine sitting in a classroom nestled in the rolling hills of the Southern California coast. It was hard to juxtapose the warm classroom and the tranquil setting with the horror of the story being recounted to us of Adm. Stockdale’s imprisonment in the infamous Hanoi Hilton for more than 7 years.

Stockdale would eventually receive the Medal of Honor, America’s highest military award of valor, for the way he conducted himself while a POW.

While I first learned of his experience when being taught the Code of Conduct, 6 rules which are meant to govern the individual behavior of service members during wartime, it is The Stockdale Paradox from Jim Collins’ wonderful book on Leadership, Good to Great, that has been on my mind lately.

The Stockdale Paradox states that leaders need to maintain, “unwavering faith amid the brutal facts.” Put differently, see the world as it is but don’t let that reality deter you from the pursuit of the opportunities available to you and your team regardless of their inherent challenges.

Confront the brutal facts

The first principle is that you must not fool yourself, and you are the easiest person to fool.

Richard Feynman

The above quote from legendary physicist Richard Feynman is one of my favorite, of his many, insights into human character. I love Feynman most for his practical philosophy of life and unvarnished take on the realities of human nature.

It is a common trap, one that I certainly have found myself in, to believe we are more clever than we actually are. One of my favorite quotes from Charlie Munger, “It’s better to have an IQ of 160 and think it’s 150 than an IQ of 160 and think it’s 200.”

Even if you are relatively clever, it’s always important to at least entertain the idea that you might be wrong. Better yet, take the time to conduct the thought experiment that not only might you be wrong, but you are wrong. If you are wrong, why would you be so? If you were forced to take the opposite position to your own, why might that position be right?

While I am a great lover of optimism, and write about it often, all tough minded optimists need to remain rationale by confronting the brutal facts of their reality. If you find yourself defending a position which is no longer valid as you learn some new information about the world, or are presented with a new perspective stop defending it. There is no shame in admitting you are wrong and changing course, but there is endless shame in staying with a course of action long after it passes its expiration date.

Good leaders do as Kipling urges, “trust yourself when all men doubt you, but make allowance for their doubting too.”

Unwavering faith

Retaining faith despite what seem to be overwhelming challenges is to me the definition of tough minded optimism. Interestingly enough, in his interview with Adm. Stockdale for Good to Great Collins asked Stockdale who didn’t make it out of the POW camps of Vietnam and Stockdale responded, “the optimists.”

As a self-described scholar of optimism, I’ve always struggled with this sentiment from one of histories figures I most admire. Over time I’ve come to believe Stockdale means those optimists who rest their hopes on success and take an unbridled optimism so divorced from reality that it becomes toxic.

Adm. Stockdale, a great admirer and scholar of the Stoics, I think would approve of the tough minded optimism which leaders must pursue to succeed despite the struggles they face. It is a resolute detachment from the outcome, but a faith your team that your capacity to solve problems is greater than the world’s capacity to create them.

Refer back to the Stockdale quote which leads off this article, “You must never confuse faith that you will prevail in the end with the discipline to confront the most brutal facts of your current reality.” Stockdale is clearly attuned to Collins’ notion of unwavering faith, but balances that faith with rationalism.

We should all do the same.

Tactics for uncovering the brutal facts

The truth does not change according to our ability to stomach it.

Flannery O’Connor

The more senior you are in your leadership journey the more distorted your reality of the world becomes. As a leader, you must then go to extra lengths to uncover the brutal facts which make up the reality your team faces.

James E. Casey, the founder of UPS, was famous for stopping UPS drivers on his commute to and from work for impromptu interviews and user feedback sessions on the conditions they faced.

Casey had an unwavering faith that the delivery drivers of UPS were the secret behind his company’s success and that the quality of their interactions with customers would largely dictate the performance of the company more broadly.

We should all follow Casey’s example. My 3 favorite tactics to do so:

  1. The skip level

  2. The ride along

  3. Do it yourself

The skip level

Skip level meetings are meetings you schedule with your direct reports, reports or those who are closest to the actual work. These meetings should never be meant as punitive fact finding missions for the performance, or lack thereof, of someone who reports to you. They are simply meant to be meetings which illuminate the inefficiencies or struggles faced by those on your team which you can alleviate.

The ride along

Sometimes, skip level meetings don’t illuminate the problems your team faces as they are still being filtered through an individual’s biases. Observing your team member do the actual work required in their day-to-day is an effective way to move past these biases for a more realistic view of reality.

Do it yourself

While DIY programs are in vogue with respect to home renovations and craft projects, they are equally valuable for leaders looking to uncover the facts. There is no better way to gain a sense of the reality your team faces than to do the work they do yourself.

If you lead a sales team, when was the last time you called a customer? If you lead a software engineering team when was the last time you checked in a line of code? If you lead a Product team when was the last time your wrote a PRD?

There’s no better substitute for reality than living it yourself. Act accordingly to uncover the brutal facts.

Conclusion

As leaders interested in building great teams it is important to remember the Stockdale Paradox, keep unwavering faith amid the brutal facts. The most important role of leaders is to keep balanced optimism while consistently working to uncover the facts.

As you work to uncover the facts keep in mind:

  1. The skip level

  2. The ride along

  3. Do it yourself

See y’all next week.