5 Key Questions for Wise Executive Career Decisions

Making good choices is the key to professional success for executives, and that goes for career decisions as well as on-the-job ones. Whether it’s a promotion, a new venture or a new position, when it comes to your career you should never settle for a “good enough” decision. Even if your window is closing fast — as it might if you’re in competition with a number of other candidates and have to give a quick answer — it’s always worth the time and effort to carefully consider your choice.

questions-keyholesIf you’re going to have to think on your feet, the good news is that you can. You need an approach that helps avoid subtle but risky judgment errors — what scholars in cognitive neuroscience and behavioral economics call cognitive biases. These mental blind spots can spell career disaster.

These mental blindspots lead to disastrous consequences in our professional and personal lives. Fortunately, recent decision science scholarship has shown how simple yet effective strategies will enable you to recognize where you and/or others on your team are vulnerable to cognitive biases. You can also use research-based techniques to protect yourself from these dangerous judgment errors and make the wisest and most profitable decisions, whether in business, in relationships, and in other life areas.

Any career decision deserves as much gravity and time as you can give it. But if you’re on a tight schedule, there’s a fast technique that uses five essential questions. Ask these of yourself and you can reduce regrets, scale back on the turmoil, and safely arrive at the best decision.

What important information have I not yet fully considered?

A common danger involves looking for evidence that only supports your preferred choice. Make sure to look twice as hard for evidence that goes against it. And instead of letting yourself just consider the first viable option, try to find other attractive options to make a wiser choice. It’s not necessarily about either staying in your job or taking the offer for another one, for instance: there are far more variations on that theme.

At the same time, don’t get stuck in “analysis paralysis” by overloading yourself with information. Focus on the information that is truly important to your decision. Ideally, you’ll already have taken the time to consider what that would be — so you don’t have to make that determination in the heat of the moment.

What relevant dangerous judgment errors have I not yet addressed?

There are many different kinds of cognitive biases, some more relevant than others to specific kinds of decisions. When we’re operating under a planning fallacy, we instinctively believe everything will go according to plan and thus fail to consider potential problems. When they happen, we’re caught off guard.

The halo effect clouds our judgment based on our impression of someone: if they have a characteristic we like or relate to, we’re inclined to think more favorably about them (and possibly, their job offer).  The opposite is the horns effect, in which a dislikable characteristic makes us think more negatively of a person — and their offer. The overconfidence effect prompts us to avoid anyone else’s constructive criticism or advice if it conflicts with our intuition. All erode the strength of sound decision making.

What would a trusted, objective adviser suggest I do?

It’s always better to have mentors, coaches, consultants, and other experts you can turn to when you’re at a crossroads. When we make decisions by ourselves we miss out on invaluable perspective and wisdom and lack a sounding board to make us consider our own opinions more objectively.

If no advisers are available, imagine the conversation instead. Given the situation, what might a trusted consultant tell you? This step can have a surprisingly powerful impact on your decision-making and help you to recognize your own blind spots.

Have I addressed all the ways my decision may not work?

Once you’re mostly settled on the decision you want to make, be ready to rethink it. As you begin to follow through with your choice, anticipate what new obstacles or issues you may face. Consider whether or not your prospects of getting the role are truly positive fit, if you really understand the terms of hire, or whether working for a new company would mean making serious adjustments to your life, for instance.

If you realize there’s more to the choice than you’d initially thought, go back and revisit the earlier stages of your question process. Consider one of the other options you generated — such as a job you applied for that didn’t seem as appealing at the time, or the idea of holding back and building a network for a future career leap instead. Would that be a better choice?

Will new information cause me to revisit the decision?

You don’t want to be burdened with buyer’s remorse and frustration — and you do want to continue striving for your objective with attention and energy. Take the time to evaluate what kind of new information would cause you to revisit your decision. You may want to set a financial trigger, such as a certain pay increase. Or establish a development trigger, such as the certainty you’ll be able to learn new skills.

Do you have a specific goal in mind, such as generating a certain number of new sales leads or completing a project within the first six months? Can you achieve these benchmarks for yourself? If you can answer this question in advance, you’ll be in a much better position to avoid later regrets.

Employ these five questions whenever you need to make decisions, and they will become second nature. The more you practice, the faster you’ll get at effectively coming to clear conclusions. A career move is never to be taken lightly, and it shouldn’t be made on the basis of gut instinct. If you catch yourself telling someone, “I’ve got a good feeling about this,” it’s time to reach for your questions, and get to work.


ExecuNet members can watch the author’s  recorded ExecuNet Master Class, “How to Avoid Disasters in Managing Your Career.”

Dr. Gleb Tsipursky

Dr. Gleb Tsipursky

An internationally-renowned thought leader known as the Disaster Avoidance Expert, Dr. Gleb Tsipursky is on a mission to protect leaders from dangerous judgment errors known as cognitive biases by developing the most effective and profitable decision-making strategies. A best-selling author, he wrote Never Go With Your Gut: How Pioneering Leaders Make the Best Decisions and Avoid Business Disasters (Career Press, 2019), The Blindspots Between Us: How to Overcome Unconscious Cognitive Bias and Build Better Relationships (New Harbinger, 2020), and Resilience: Adapt and Plan for the New Abnormal of the COVID-19 Coronavirus Pandemic (Changemakers Books, 2020). He has over 550 articles and 450 interviews in Inc. Magazine, Entrepreneur, CBSNews, Time, Business Insider, Government Executive, The Chronicle of Philanthropy, Fast Company, and elsewhere.

CBS News, Time, Business Insider, Inc. Magazine, and elsewhere. His expertise comes from over 20 years of consulting, coaching, and speaking and training experience as the CEO of Disaster Avoidance Experts, and over 15 yearsin academia as a behavioral economist and cognitive neuroscientist.

Contact him at Contact him at Gleb[at]DisasterAvoidanceExperts[dot]com, follow him on Twitter @gleb_tsipursky, on Instagram @dr_gleb_tsipursky, and on LinkedIn, and register for his free Wise Decision Maker Course.

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