trigger a moment of reflection, interrupting us in the moment. Popping out of the moment like that can remind us of why we took the trouble to list terms that signal potential decision traps.
The swear jar is a simple example of a Ulysses contract in action: we think ahead to a hazard in our decision-making future and devise a plan of action around that, or at least commit that we will take a moment to recognize we are veering away from truthseeking. Better precommitment contracts result from better anticipation of what the future might look like, what kinds of decisions we want to avoid, and which ones we want to promote. That takes thoughtful reconnaissance.
Reconnaissance: mapping the future
Operation Overlord, the Allied forces operation to retake German-occupied France starting in Normandy, was the largest seaborne invasion in military history. It involved planning and logistics on an unprecedented scale. What if the forces were delayed at the start by bad weather? What if the airborne landing force had trouble communicating by radio due to the terrain? What if significant numbers of paratroopers were blown off course? What if currents interfered with the beach landings? What if the forces on the different beaches remained separated? Countless things could go wrong, with tens of thousands of lives at stake and, potentially, the outcome of the war.
All those things did go wrong, along with many other challenges encountered on D-Day and immediately thereafter. The Normandy landings still succeeded, though, because they prepared for as many potential scenarios as possible. Reconnaissance has been part of advance military planning for as long as horses have been used in battle. The modern military, of course, has evolved from sending scouts by horse and reporting back to the main forces to planes, drones, satellites, and other high-tech equipment gathering information about what to expect in battle.
The Navy SEAL team that caught and killed Osama bin Laden wouldn’t have entered his compound without knowing what they would find beyond the walls. What buildings were there? What was their layout
and purpose? What differences might it make if they conducted the raid in different kinds of weather or different times of day? What other people would be present and what risks would they pose? What would they do if bin Laden wasn’t there? What was the team trying to commit to, given what they knew about each of those things (and, of course, numerous others)?
Just as they relied on reconnaissance, we shouldn’t plan our future without doing advance work on the range of futures that could result from any given decision and the probabilities of those futures occurring.
For us to make better decisions, we need to perform reconnaissance on the future. If a decision is a bet on a particular future based on our beliefs, then before we place a bet we should consider in detail what those possible futures might look like. Any decision can result in a set of possible outcomes.
Thinking about what futures are contained in that set (which we do by putting memories together in a novel way to imagine how things might turn out) helps us figure out which decisions to make.
Figure out the possibilities, then take a stab at the probabilities. To start, we imagine the range of potential futures. This is also known as scenario planning. Nate Silver, who compiles and interprets data from the perspective of getting the best strategic use of it, frequently takes a
scenario-planning approach. Instead of using data to make a particular conclusion, he sometimes takes the approach of discussing all the scenarios the data could support. In early February 2017, he described the merits of scenario planning: “When faced with highly uncertain conditions, military units and major corporations sometimes use an exercise called scenario planning. The idea is to consider a broad range of possibilities for how the future might unfold to help guide long-term planning and preparation.”
After identifying as many of the possible outcomes as we can, we want to make our best guess at the probability of each of those futures occurring.
When I consult with enterprises on building decision trees and determining probabilities of different futures, people frequently resist having to make a guess at the probability of future events mainly because they feel like they can’t be certain of what the likelihood of any scenario is. But that’s the point.
The reason why we do reconnaissance is because we are uncertain. We don’t (and likely can’t) know how often things will turn out a certain way with exact precision. It’s not about approaching our future predictions from a point of perfection. It’s about acknowledging that we’re already making a prediction about the future every time we make a decision, so we’re better off if we make that explicit. If we’re worried about guessing, we’re already guessing. We are already guessing that the decision we execute will result in the highest likelihood of a good outcome given the options we have available to us. By at least trying to assign probabilities, we will naturally move away from the default of 0% or 100%, away from being sure it will turn out one way and not another. Anything that moves us off those extremes is going to be a more reasonable assessment than not trying at all.
Even if our assessment results in a wide range, like the chances of a particular scenario occurring being between 20% and 80%, that is still better than not guessing at all.
This kind of reconnaissance of the future is something that experienced poker players are very familiar with. Before making a bet, poker players consider each of their opponents’ possible responses (fold, call, raise), and the likelihood and desirability of each. They also think about what they will do in response (if some or all of the opponents don’t fold). Even if you don’t know much about poker, it should make sense that a player is better off considering these things before they bet. The more expert the player, the
further into the future they plan. Before making that decision to bet, the expert player is anticipating what they’ll do following each response, as well as how the action they take now affects their future decisions on the hand. The best players think beyond the current hand into subsequent hands: how do the actions of this hand affect how they and their opponents make decisions on future hands? Poker players really live in this probabilistic world of, “What are the possible futures? What are the probabilities of those possible futures?” And they get very comfortable with the fact that they don’t know exactly because they can’t see their opponent’s cards.
This is true of most strategic thinking. Whether it involves sales strategies, business strategies, or courtroom strategies, the best strategists are considering a fuller range of possible scenarios, anticipating and considering the strategic responses to each, and so on deep into the decision tree.
This kind of scenario planning is a form of mental time travel we can do on our own. It works even better when we do it as part of a scenario- planning group, particularly one that is open-minded to dissent and diverse points of view. Diverse viewpoints allow for the identification of a wider variety of scenarios deeper into the tree, and for better estimates of their probability. In fact, if two people in the group are really far off on an estimate of the likelihood of an outcome, that is a great time to have them switch sides and argue the other’s position. Generally, the answer is somewhere in the middle and both people will end up moderating their positions. But sometimes one person has thought of a key influencing factor the other hasn’t and that is revealed only because the dissent was tolerated.
In addition to increasing decision quality, scouting various futures has numerous additional benefits. First, scenario planning reminds us that the future is inherently uncertain. By making that explicit in our decision- making process, we have a more realistic view of the world. Second, we are better prepared for how we are going to respond to different outcomes that might result from our initial decision. We can anticipate positive or negative developments and plan our strategy, rather than being reactive. Being able to respond to the changing future is a good thing; being surprised by the changing future is not. Scenario planning makes us nimbler because we’ve considered and are prepared for a wider variety of possible futures. And if