Embrace the Messiness
You might be tempted to score each opportunity based on the different factors (e.g., 2 out of 3 for sizing, 1 out of 3 for market factors, and so on) and then stack-rank your opportunities, much like you might do with features. Don’t do this. This is a messy, subjective decision, and you want to keep it that way.
Remember, you aren’t making absolute judgments. You are making relative judgments by comparing and contrasting sibling opportunities against each other. You don’t need to score each opportunity. This will take a lot of work, will be rife with assumptions, and won’t lead to a better decision. Instead, make a data-informed, subjective comparison for each set of factors.
There may not be a clear winner, and that’s okay. One opportunity might look like the winner based on sizing, and another might look like the winner based on company factors. Yet another might look like the winner based on customer factors. Your job as a team is to have a healthy debate. Consider the different dimensions, and make the best decision that you can for this moment in time. Think about each set of criteria as a different lens through which to view impact. Use the lenses to fuel your conversation.
When we turn a subjective, messy decision into a quantitative math formula, we are treating an ill-structured problem as if it were a well-structured problem. The problem with this strategy is that it will lead us to believe that there is one true, right answer. And there isn’t. Once we mathematize this process, we’ll stop thinking and go strictly by the numbers. We don’t want to do this.
Instead, we want to leave room for doubt. As Karl Weick, an educational psychologist at the University of Michigan, advises in the second opening quote, wisdom is finding the right balance between having confidence in what you know and leaving enough room for doubt in case you are wrong.32 That’s the balance we are looking for here. When we treat this like the messy, subjective decision that it is, we are leaving room for doubt, so that, down the road, if we learn we are addressing the wrong opportunity, we will be far more likely to course-correct.