The time to take counsel of your fears is before you make an important battle decision.” – General George S. Patton, Jr.

It was the spring of 2003, and I was leading a group of vehicles as we bypassed an area known to be populated by loyalists to Saddam Hussein. Our route had been set by the brigade operations officer and snaked through and around Saddam’s birthplace of Tikrit, an obligatory obstacle on the road to Mosul, our destination. As the lead element of a much larger convoy, our march north had gone perfectly. Until it didn’t.

Stretching across the road in front of us was a very low train bridge. There was just enough room to get a HMMWV under the span, but not enough for the larger cargo trucks trailing behind me. Unable to raise the command net on the tactical radio and with an inoperative mobile subscriber equipment system – it had been scavenged for parts to repair another node – next to me, I quickly weighed my options. Remaining in place was a bad idea, since a gaggle of American military vehicles was sure to draw unwanted attention. Abandoning the cargo trucks was out of the question because they carried much of our ammunition. That left scouting a crossing point, which carried an incalculable amount of risk because the dirt road that ran along the tracks could easily be mined. We weren’t exactly in a friendly part of the country.

We would scout the route. And, since I wasn’t willing to delegate that high-risk task to anyone else, my driver and I pulled off the main road and slowly – and I mean slowly – followed the tracks in search of a level crossing. After several hundred yards, we crossed the tracks and repeated the process back to the main road. The route was clear, with no obvious signs of mines or improvised explosive devices. We returned and led the serial to the crossing and back onto the main road, where we continued our otherwise uneventful journey north.

Risk, time, and opportunity

The challenge most people face when making decisions that involve risk is time. We think too long about the decision, delaying to either work through some extended risk management calculus or in a vain attempt to negotiate down the risk to an acceptable level in our mind. But there’s a problem with that kind of thinking.

Risk is a potent catalyst that fuels opportunity. When I first wrote those words nearly two decades ago, I was trying to convey the relationship between risk, time, and opportunity in decision-making. The key is to find the sweet spot, to make the decision when the danger of the risk doesn’t outweigh the value of the opportunity. Make the decision too early, and the risk becomes a gamble; you don’t want your future depending on a lucky roll of the dice. Make the decision too late, and the opportunity is either gone or so devalued that it doesn’t matter; you missed your chance.

THE KEYS TO SUCCESS

In truth, every decision we make involves some level of risk. The degree of that risk is a measure of the inherent uncertainty of achieving the desired outcome. The greater the uncertainty, the higher the risk. And for people uncomfortable with uncertainty and ambiguity, the perceived risk is higher still. The adage “paralysis by analysis” is a reflection of this phenomenon, when someone simply can’t overcome the fear of uncertainty to make a necessary decision.

Making risky decisions is part of being a leader, something not for the faint of heart. If those decisions make you uncomfortable, do something about it. Either defer leadership opportunities to those willing to make those hard decisions or learn how to make them yourself. Start with a simple model and build the experience (and courage) required to make risky decisions.

1. What is the likelihood of success?

Making data-informed decisions is nothing new, but the science of interpreting the data is improving every day. Listen to the narrative the data is conveying, but also listen to your gut. Experience is a mentor unlike any other.

2. What can you do to improve the odds?

Decision-making is typically a process that involves other decisions, all of which bear on the long-term outcome. Systems thinking allows you to see the bigger picture and find ways to reduce uncertainty while improving your chances for success.

3. What are your options for less-than-ideal results?

Oftentimes, our decisions don’t lead to the outcomes we’d hoped for. Living with those outcomes is a lot easier if the decisions get us closer to our ultimate destination. In the military, we build branches and sequels into our planning based on the possible outcomes of an operation. You have options if you think them through.

4. What are the costs of failure?

Be crystal clear about this. Failure should never equate to becoming a legendary meme – “At least you didn’t die” – or a recipient of a Darwin Award. Define acceptable risk before you make that decision and ensure that you are willing to take that path.

5. What do you gain from making the attempt?

Wayne Gretzky famously said, “You miss 100% of the shots you don’t take.” What he didn’t say was that he gained two things from every shot he took: experience and knowledge. You might not end up in the Hall of Fame for making risky decisions, but you will grow in the process.

Making risky decisions isn’t something that should come quickly or with relative ease. Like anything in life, getting good at making risky decisions requires that you put in the reps. Practice making those decisions in situations where you can control the variables, or where the risk of failure is minimal. Wargaming and case studies make for good proving grounds, where you can hone your decision making skills and, with the possible exception of Leeroy Jenkins, not become infamous in the process.

 

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Steve Leonard is a former senior military strategist and the creative force behind the defense microblog, Doctrine Man!!. A career writer and speaker with a passion for developing and mentoring the next generation of thought leaders, he is a co-founder and emeritus board member of the Military Writers Guild; the co-founder of the national security blog, Divergent Options; a member of the editorial review board of the Arthur D. Simons Center’s Interagency Journal; a member of the editorial advisory panel of Military Strategy Magazine; and an emeritus senior fellow at the Modern War Institute at West Point. He is the author, co-author, or editor of several books and is a prolific military cartoonist.