Make Better Decisions By Questioning Your Assumptions

When you find yourself with two seemingly incompatible goals, needs, or desires, ask yourself what it would take to achieve both outcomes simultaneously.

No, seriously.

Although it’s true that every decision you make eliminates another option or possibility, in the sense that the dollar you spend on lunch can’t also be put into your bank and the hour you spend at the gym can’t also be spent cleaning the kitchen, many of us are too quick to assume that certain goals naturally conflict with each other.

If we accept more responsibility at work, we’ll have to spend less time at home.

If we have children, we won’t be able to travel.

If we want to save enough money to retire, we won’t be able to buy lattes.

Dialectical questioning — a method of argument that has been around since Socrates and Plato — allows you to investigate your assumptions and identify scenarios that defy those assumptions.

As leadership coach Jesse Sostrin explains, in Strategy+Business:

Pham wanted to land the next promotion, but the workload and quality of life compromises required to get it felt unsustainable to her. Both outcomes — either getting the promotion or foregoing it to maintain better work–life balance — aligned with her values (achievement, success, family, health, etc.) and each felt important. Yet the two outcomes seemed incompatible.

A dialectical question made room for the combination of both: “How can I continue growing as a leader and advancing in my career while designing my leadership lifestyle in a healthier way?” Pham used this question to actively guide her thinking and action toward a result that included satisfying elements of both outcomes. That result was a conscious choice to submit to longer hours every other week, with a biweekly reduction in travel. Negotiating this flexibility allowed her to reconnect with friends and family and resume her yoga practice, which she’d neglected.

Notice that Pham’s solution did in fact involve making choices that eliminated certain options — she’ll be working more hours some weeks, which means she won’t be able to spend that time with friends and family, but she’ll have fewer working hours other weeks and can use that time to connect with the people she cares about.

Not all of us can choose our own work hours, of course. That doesn’t mean we can’t use the dialectic method to reconcile other aspects of our lives that appear to be in conflict. If you ask yourself “how can I have my daily latte and contribute to my retirement fund,” to use the classic-but-clichéd example, you might find another area in which you are able to cut back on your spending — or if you discover that your budget is too tight, you might start asking yourself how you can earn more money.

This method is very similar to the Fourth Habit of the famous Seven Habits of Highly Effective People: Think Win-Win. What would have to happen for everyone in this scenario to get what they want? What choices would need to be made, what boundaries would need to be set, and what possibilities would need to be considered?

So — the next time you find yourself in a situation where you have to choose between two seemingly incompatible paths, start asking yourself whether there’s a third path you haven’t yet considered. What would it take to get both A and B? What are you assuming about the situation, and what happens if you assume the opposite? Is there a way you can adjust C to make A and B more compatible with each other?

Once you know the answers to these questions, you’ll have a better understanding of how to move forward.

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