When I was considering a move for my family from one country to another, the decision loomed over me. It lived large in my mind, day and night. Whichever way I chose, I was going to be giving up something that mattered to me. Staying would have limited future career and educational opportunities for me and my children. Going meant leaving behind family, close friends and a place I loved. The stakes were high and making the wrong call would be hard to undo.
Most decisions are nothing like that. We all make small stakes decisions everyday, like deciding what to wear, what to eat, and what to watch. Sometimes it’s determining whether it’s time to put your home up for sale or change careers. The decisions we make vary significantly in scope and complexity.
We make hundreds of them a day, and thankfully most don’t call for late-night rumination. From time to time, however, we face decisions that are incredibly difficult to make.
What’s a Dilemma?
Dilemmas are decisions that must be made when the available choices are equally unappealing or may solve one problem while creating another. There’s seldom a clear choice with dilemmas, and all options, even inaction, carry the potential for loss. Dilemmas can be a struggle between our hearts and minds or merely a predicament of circumstances. The saying “on the horns of a dilemma” refers to the possibility of being impaled by either unpleasant choice. That’s a pretty accurate metaphor.
Whether business, social, moral or ethical, we’ve all faced dilemmas. Tough decisions are part of the landscape of the business world, and I would hazard a guess that the dilemmas leaders face are harder than ever. For example, do we continue to introduce large-scale organizational change even though people are feeling change fatigue? How aggressively should we integrate AI without losing quality, trust, or our people? How rigid do we make our in-person work policies?
How to Work Through a Dilemma
While there are no easy answers to dealing with a dilemma’s horns, there are some things that may help us work through complex problems.
Understand Our Brain and Our Biases
It’s important to be aware of how our brain processes decisions. For many decades, researchers have studied the cognitive factors involved in decision-making and have identified numerous mental shortcuts that we use unconsciously. Known as heuristics, these shortcuts can show up as cognitive biases that can hinder rather than help us make smart decisions. Researchers have catalogued dozens of these biases (sometimes called effects, traps, fallacies or cognitive errors) that can distort our decision-making. Each one can derail the good judgment and rational thinking that sound decisions depend on.
Decision-making experts suggest using checklists to de-bias our thoughts. There are numerous frameworks available to detect and challenge heuristics that can cause potential blind spots. However, as researchers Daniel Kahneman, Dan Lovallo and Olivier Sibony point out, awareness of our biases alone is not enough to eliminate them because we aren’t very good at recognizing or confronting our own flaws.
Discuss the Dilemma With Someone You Trust
Research has shown that including others in the decision-making process can challenge our thinking and illuminate potential distortions. However, while we may be good at bringing others into the decision-making fold, it is usually to get their perspective, ask for advice or seek guidance.
In other words, we turn to others hoping that they may have an answer that we don’t have. Rather than seeking advice alone, involving someone who can ask open-ended questions prompts a deeper exploration of the issue, surfaces the biases we can’t see in ourselves and leaves us better equipped to decide. This is where executive coaching can be particularly helpful.
Manage Dilemmas With a Coach
Accredited coaches are rigorously trained to ask questions that stretch our thinking and help us gain deeper awareness of our beliefs. A few examples of what a coach might ask a client caught on the horns of a dilemma:
- What would someone with an alternative view think about this?
- What other information would you need to make a better decision?
- What would be the worst-case scenario?
- What is the ideal outcome?
- What decision would best reflect your values?
Being asked open-ended questions can shine a light on our beliefs and cognitive biases that shape our worldview and, ultimately, our decision-making. Coaching is grounded in the belief that asking open-ended questions empowers us. It helps us self-reflect, reframe and create actionable steps towards solutions.
Good questions do something else, too. They help us work out whether the problem we are facing is solvable at all. Barry Johnson, who developed the polarity management model, distinguishes between problems that can be solved and polarities that cannot.
For example, interdependent opposites such as centralization and autonomy, or speed and quality, where picking one side and neglecting the other, guarantees you will pay for it eventually. The aim with a polarity isn’t to choose. It’s to get the best of both while avoiding the limits of each. Advice struggles here, because there is no single answer to hand over. Questions are how you tell a true dilemma from a tension you will be managing for years, and how you learn to hold that tension well.
Conclusion
Of course, we may not always have the luxury of deep contemplation before making a decision. Sometimes decisions must be made quickly and with little information. We go with what our gut tells us because that’s all we have at the moment. But often we’ll encounter situations that allow us to press pause before making a choice. When this happens, take a moment to ask yourself who you can recruit to ask the questions you haven’t thought to ask yourself.
That is what shifted things for me. After months of turning the choice over, a close friend asked me: “If I were the one facing this, what would you tell me to do?” She didn’t offer an opinion. She moved me out of my own head, and the answer I gave her was the one I hadn’t been able to give myself. We moved, and while the choice didn’t get any easier, the horns felt a good deal less sharp.
