If you’re struggling with a decision, the following six questions can provide a useful jolt to your thinking. All of them rely on a sudden impact — a quick shift in perspective or a forced re-framing of a dilemma.
1. Imagine that the option you are currently leaning towards simply vanished as a feasible alternative. What else could you do?
WHY THIS QUESTION WORKS: A very common decision-making trap is “narrow framing”, which means we get stuck in one way of thinking about our dilemma, or that we fail to consider other options that are available to us. By forcing ourselves to generate a second alternative, we can often surface a new insight.
2. Imagine that the alternative you are currently considering will actually turn out to be a terrible decision. Where could you go looking for proof of that right now?
WHY THIS QUESTION WORKS: Probably the most pernicious enemy of good decision-making is ‘confirmation bias’, which is our tendency to seek out information that supports what we want to be true, while failing to be as eager in hunting for contradictory information. This question compels you to search for disconfirming information.
3. How can I dip a toe in this decision without diving in headfirst?
WHY THIS QUESTION WORKS: When deciding what will be good for themselves, people typically make a guess. Think of the undergraduate student who enrols in law school, thinking she’ll love the life of a lawyer, or the information worker who quits his job to get a graduate degree in Social Work, convinced it will allow him to live a more meaningful life. But there is no reason to guess when you can know. The first student can spend three months interning in a law firm (or better yet, one month each in three different firms), and the information worker can shadow a real social worker on weekends or evenings. We call this an ‘ooch’ — an experiment that arms you with real-world information about your options.
4. What would you tell your best friend to do, if he/she was in the same situation?
WHY THIS QUESTION WORKS: This may be the single-most powerful question we discovered for resolving personal decisions. It sounds deceptively simple, but we’ve witnessed first-hand the power of this question: We’ve consulted with people who were agonizing about a decision for months, and when we ask them this question, an answer pops out of their mouth in 10 seconds, often surprising them.
5. If you were replaced tomorrow, what would your successor do about your dilemma?
WHY THIS QUESTION WORKS: This is the professional version of the ‘best friend’ question. Like that question, it relies on a simple shift in perspective to help you detach from short-term emotion and see the bigger picture more clearly. In his autobiography, Andy Grove, the former CEO of Intel, tells a great story about using this question to resolve one of the most difficult decisions of his career.
6. Six months from now, what evidence would make me retreat from this decision? What would make me double-down?
WHY THIS QUESTION WORKS: One curious thing about our decision-making is that we treat our choices as permanent when, in virtually all cases, they’re provisional. For example: We think (but don’t know) that a certain employee is the right fit for an open position; we think (but don’t know) that we’d enjoy starting our own business; we think (but don’t know) that John’s social media plan will be effective. So, given that our decisions are simply our ‘best guesses’ at a particular point in time, shouldn’t we pay more attention to the circumstances that would make us reconsider?
And lastly, a bonus RED FLAG: Beware of ‘whether or not’ decisions. If a friend or colleague comes to you with a ‘whether or not’ decision — ‘I’m debating whether or not to quit my job’, ‘I’m deciding whether or not to buy a new iPad’ — that’s a sign that they may be caught in a narrow frame (they’re only considering one option when, chances are, they have many). Try prodding them with question #1. 
Chip Heath is the Thrive Foundation for Youth Professor of Organizational Behaviour at Stanford’s Graduate School of Business. Dan Heath is a Senior Fellow at Duke University’s CASE center, which supports social entrepreneurs. The brothers are the co-authors of three New York Times bestsellers: Decisive, Switch and Made to Stick.
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This article appeared in the Fall 2018 issue. Published by the University of Toronto’s Rotman School of Management, Rotman Management explores themes of interest to leaders, innovators and entrepreneurs.
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