Everyone hits a crossroad from time to time. We get stuck in a state of indecision on a problem that seems to have no correct answer, and at times, it can be maddening.
The most important decisions, whether in work or in life, never really seem to fall in the black or white. They linger in the gray, where they can remain for a dangerously long time. The journalist Hunter S. Thompson once wrote, "A man who procrastinates in his choosing will inevitably have his choice made for him by circumstance."
Instead of letting circumstance make your next vital decision, Joseph L. Badaracco, the John Shad professor of business ethics at Harvard Business School, believes that the answer will reveal itself after answering five important questions.
As Badaracco writes in the Harvard Business Review:
Where do these questions come from? Over many centuries and across many cultures, they have emerged as men and women with serious responsibilities have struggled with difficult problems. They express the insights of the most penetrating minds and compassionate spirits of human history. I have relied on them for years, in teaching MBA candidates and counseling executives, and I believe that they can help you, your team, and your organization navigate the grayest of gray areas.
The first step in making any important decision, suggests Badaracco, is to objectively analyze all of the possibilities, and consider their real-world outcomes. He explains that this process needs to be distinguished from a cost-benefit analysis, and shouldn't be limited to outcomes that can be measured or counted. After all, if numbers and data could solve this query, they wouldn’t be in the gray zone in the first place.
"Your job is to put aside your initial assumption about what you should do, gather a group of trusted advisers and experts, and ask yourself and them, ‘What could we do? And who will be hurt or helped, short-term and long-term, by each option?" writes Badaracco.
While this task is more difficult than it seems, it’s a strategy that chess players learn to master. The game requires players to look at the board and reimagine how it will shift based on theirs and their opponent’s decisions.
"You’re constantly looking two, three, four moves ahead," entrepreneur and former star of the youth chess circuit Justin Moore once told Fast Company. "If you do this move, what’s the countermove? What are all the countermoves? And then for all of those, what are all of my potential countermoves? Chess is constantly teaching you to think about what comes next, and what comes after that, and what the repercussions could be," Moore explained.
Whether it’s your boss, your shareholders, or your children, the decisions we make in life will often affect those around us, and we must consider our obligations to each stakeholder, says Badaracco. He adds that we will often be tempted to only consider immediate stakeholders, most likely the ones that sign our paychecks, but big decisions require us to consider the deeper responsibility of our actions.
"How can you figure out specifically what these duties oblige you to do in a particular situation?" he writes.
By relying on what philosophers call your ‘moral imagination.’ That involves stepping out of your comfort zone, recognizing your biases and blind spots, and putting yourself in the shoes of all key stakeholders, especially the most vulnerable ones.
This question requires us to consider the contextual circumstances of our decisions in a realistic way, the way the world really exists today, rather than the way we would like it to.
"After considering consequences and duties, you need to think about practicalities: Of the possible solutions to your problem, which is most likely to work? Which is most resilient? And how resilient and flexible are you?" writes Badaracco. "To answer those questions, you need to map the force field of power around you: Who wants what and how hard and successfully each person can fight for his aims."
This self-reflective question, explains Badaracco, forces us to consider how our decisions shape the person or organization we really are, and not the one we want or imagine ourselves to be. By acknowledging that such decisions shape our sense of self, he believes that an understanding of the self is vital in the decision-making process.
"This question asks you to step back and think about your decision in terms of relationships, values, and norms," he writes. "What really matters to your team, company, community, culture? How can you act in a way that reflects and expresses those belief systems? If they conflict, which should take precedence?"
To help arrive at this answer, Badaracco suggests thinking about the decision as a chapter in a person or company’s history, and how that chapter would fit into the overall narrative. "Of all the paths you might choose in this gray area, which would best express what your organization stands for?" he writes.
Good judgment, Badaracco writes, is as much about understanding and analyzing the situation as it is about staying true to our values and ideals. Ultimately, the big decisions force us to determine what matters most and what matters least.
"How will you figure out what you can live with?" asks Badaracco. "End your conversations with others, close the door, mute the electronics, and stop to reflect. Imagine yourself explaining your decision to a close friend or a mentor—someone you trust and respect deeply. Would you feel comfortable? How would that person react?"