9 Lessons for Making High Risk Decisions

Risk and decision-making under pressure are an inherent part of all our lives. Today we are watching two international figures representing their nations who are locked in mortal combat—Vladimir Putin and Volodymyr Zelensky. Both “risking it all” in very different ways with unpredictable outcomes.

In my latest book, To Risk It All: Nine Conflicts and Crucible of Decision, I’ve looked at the history of the U.S. Navy and those who had to make pressure-packed decisions under extreme circumstances. Their stories offer many lessons, and they’ve helped me in my own experiences as an admiral both in war and peace. But you don’t have to be a sailor to learn from these examples. What have I learned that applies for us all?

Gather all the intelligence. So often choices are made with a faulty understanding of the simple facts. We should be aware of the phenomenon of “belief bias,” applying what you think ought to be happening to what is actually unfolding. A classic case of this was the shoot down of an Iranian airliner by USS Vincennes, an AEGIS cruiser in the Arabian Gulf in July 1988. The ship was fearing attack by Iranian fighters—and tragically mistook a passenger aircraft for an enemy F-14. Beware of confusing assumptions (things you think are true) and facts (things that are indisputable.) Chances are, Putin believed his invaders would be greeted as liberators and that his army was invincible.

Understand the timeline. Often people approaching decisions put themselves under artificial or self-imposed deadlines. Pushing back to get more time before committing is always worth attempting. You should never commit to a course of action before you must. I’ve seen various bosses I’ve worked for avoid “lunging at the ball,” instead finding a bit more time and space to make an informed decision. Among the best of all in this regard was Secretary of the Navy Richard Danzig, who could at times be a bit maddening in how he would ask for more information, another report from the fleet, a re-briefing on options. But over more than two years as his executive assistant and senior navy aide, I never saw him make a bad decision, from pushing for women to be assigned to nuclear submarines, to investigating a terrible collateral damage bombing incident on the island of Vieques in the Caribbean. President Barack Obama, for whom I served for over four years as Supreme Allied Commander at NATO, also had that kind of patient, “wait for the facts” attitude, and refused to be rushed into a decision until he was comfortable he had all the information or events simply demanded a decision be made.

Methodically consider the possible outcomes of your decision—both good and bad. This sounds so obvious, but on countless occasions I’ve seen smart, gifted people make decisions without really considering the full range of outcomes, especially in the negative direction. Again, I suspect that Vladimir Putin never imagined the quagmire he now finds himself in or weighed the risks and rewards. In my book, I tell the story of then Rear Admiral Michelle Howard who led the Navy operation tasked with trying to rescue civilian mariner Captain Phillips who had been taken hostage by pirates. She had to look at the range of potential outcomes—a clean success including the capture of the pirates; a failure and the death of Captain Phillips; some mixture of the two, with Phillips receiving a severe or a lesser wound, perhaps accidentally shot by a SEAL; the pirates negotiating a conclusion, on and on. In this phase of decision making, it is important to neither take counsel excessively of your fears nor become emotionally involved in an unrealistic result. Good decision makers can boil the outcomes down to a handful of realistic scenarios, then evaluate them against each other. The key is being brutally honest about the range of outcomes. I see this skill on display in the actions of President Zelensky.

Evaluate the resources. This requires clear-eyed skepticism. Necessary supplies will almost never arrive early, equipment will break-down, events will tend to stretch out, people will get tired, and on and on. In the disastrous Iranian hostage rescue effort in 1979 known as “Desert One,” pretty much everything that could go wrong did go wrong. The decision makers should have anticipated the failure rates and programmed more buffer into the system Those lessons were deeply absorbed by the special operations community, which has evolved into the most planning-oriented part of the US military. As I was anticipating the chances of a hostage rescue operation in Colombia in 2006-2009, I was astounded by the level of detail and redundancy built into the work of the special operations teams from the Delta Force assigned to work with me. They had an enormous level of resources available, to include building an exact “mockup” of the jungle clearing where we thought the hostages were being held, then using it to rehearse endlessly. In the war in Ukraine, clearly the invaders had not thought through their logistical challenges while Zelensky’s forces, aided by allies, excelled in preparation.

Focus on your people—but don’t be paralyzed with fear over their wellbeing. Whether you are leading a five thousand person crew on an aircraft carrier, or a three person team on the sales force at Google, decisionmakers have an obligation to understand the impact their choices will have on the people working for them. That does not mean they should become paralyzed with the thought that some of your people will suffer, especially in a military context. Finding the balance between literally “throwing people at the problem” (like many US Civil War commanders, or generals in World War One did) and taking calculated risks while keeping the mission and objective firmly in sight is the key. Here we see Putin failing and achieving massive casualties, while Zelensky is finding the balance well.

Don’t get emotionally involved in people who are roadblocks. One of the greatest books ever written about leadership and decision making is Mario Puzo’s 20th century classic The Godfather. The book is replete with examples of decision making both good and bad, and a central lesson is never to “hate your enemies” because it can cloud your judgement—and your decision making skills. Putin’s failures here are obvious.

Be willing to change your mind. I remember when I first took the venerable college entrance exam, the Scholastic Aptitude Test (SAT), the advice I received was “go with your first answer.” I followed it, even when I read over the question again and thought “wait a minute, I bet that isn’t right.” Over time, however, studies have shown that the idea of always “going with the first answer that occurs to you” actually creates a lower probability of a correct answer. Decision makers should be willing to assess a situation and change their mind and will very often improve the outcome they seek. Being prepared to step out of line with previous training can sometimes be the best decision of all. The creativity of the Ukrainian commanders is noteworthy example of this.

Be determined. So often, decision making is hard because we dither, worrying about what will occur. You cannot predict the future with certainty, of course, but determination—a willful approach to problems—can be a tonic in moments of indecision. When I find myself mentally shuttling back-and-forth between “options,” I think about John Paul Jones, one of America’s earliest naval commanders who helped secure victory in the American Revolution. He was wrong in many things in his very eventful life, but the reason he is remembered today is that he was ruthlessly determined about a key decision he made in USS Bonhomme Richard—to fight on. Unfortunately Putin appears very determined, but he has encountered a leader who is even more certain of his course of action in Volodymyr Zelensky.

Be prepared to execute. Decision making is not the end of most situations, but often the beginning. Even as you mentally conclude with the choice ahead of you, realize that communicating and advocating the decision is often as important as generating it. Declaring success—knowing how to telegraph success, the use of optimism as a force multiplier in decision-making and knowing when to “find the exit” are all key. But I know the pressure of such moments, where time seems to compress, and options become more limited with every tick of the clock. That is the moment when I have tried to make time slow down, at least in my own frame of mind. It is when your voice should become calmer, your breathing more regular, your information scanning more deliberate—all of which is easy to say and very, very hard to do. Some of the “tricks of the trade” are outlined above but let me end with a last thought: the ability to make good decisions is like a muscle—it must be exercised carefully, trained to perform at peak readiness, and treated with respect.

We all make dozens of decisions every day, but once in a great while some of us must make truly hard decisions under a high degree of pressure, often with little time to ponder the pros and cons. A significant part of making the best possible decision under those circumstances involves what we do in the years before we face it. Thus, it is that conscious preparation, life-long study, and the cultivation of a willingness to act and avoid paralysis in the face of crisis become the keys—knowing all the while that what we decide may well not result in the outcomes we want.

We all must face the simple fact that no one’s decisions are always right—I have made bad choices too many times to count. But whenever I’ve been faced with a truly hard choice, both at sea and ashore, I’ve put my faith in what I’ve learned along the voyage of life, at first from my parents and teachers, over time from my family and friends, and to some degree from the hard preparation of studying history and looking for role models who sailed before me. My hope in writing To Risk It All is first and foremost that you never in fact have to risk it all; but if you do, by contemplating examples of tough decisions sailors have made through our Navy’s history, you will have gained a better of chance of making the right choices and thus finding the elusive balance between impulsive determination and thoughtful balance—in the very crucible of decision.

Godspeed and open water in all the choices you make.

Adapted FROM TO RISK IT ALL by Admiral James Stavridis, USN, published by Penguin Press, an imprint of Penguin Publishing Group, a division of Penguin Random House, LLC. Copyright © 2022 by James Stavridis.