Jeff Bezos' Favorite Interview Question: A Brilliant Insight or a Psychological Trap?

There’s a certain mythology around the interview questions asked by famous CEOs. They get repeated in books, LinkedIn posts, and MBA case studies like they’re gospel. One of the most quoted comes from Jeff Bezos:

“Are you a lucky person?”

It’s simple. Disarming. Maybe even a little weird. And apparently, it’s one of his favorites. Supposedly, your answer tells the interviewer everything they need to know about your outlook, your psychology, and even your leadership potential.

But does it? Or are we just overly obsessed with the cult of clever interview questions?

Let’s break it down.

What Is This Question Actually Measuring?

The popular take is that this question measures locus of control, a psychological framework describing whether people believe outcomes in their lives are driven by their own actions (internal) or by external factors like chance or fate (external).

People who say “Yes, I’m lucky” are often framed as optimistic, glass-half-full types. They’re perceived as resilient, positive, and adaptable. Those who say “No” might be viewed as cynical or overly self-reliant, less coachable maybe.

But that interpretation is far too simplistic.

Believing in “luck” can stem from gratitude, humility, or even survivor’s guilt. I’ve met first-gen professionals who say they’re lucky just to be in the room, not because they didn’t earn it, but because they know how many barriers existed before they got there. Conversely, I’ve met people who claim full ownership of every win, but never acknowledge privilege, timing, or systemic advantage.

In other words, this question might tell you something about someone’s narrative, but not necessarily their mindset or leadership potential.

Luck Isn’t Binary, and Neither Are People

Here’s the issue with trying to bucket people into “lucky” or “not lucky.” It ignores complexity.

A lot of driven professionals have made their own luck. They put in the work, but they also know that timing, mentorship, health, and sheer randomness played a role. If you’re hiring for someone thoughtful, strategic, and self-aware, those nuances matter more than a binary answer.

And if your reaction to someone saying “No, I don’t think I’m lucky” is to eliminate them from the candidate pool, you might be filtering out people with grit, realism, or strong internal motivation. These traits often correlate with top performers.

Does This Work for Everyone or Just Certain Profiles?

We also have to ask: who is this question designed for?

In many white-collar hiring environments, cultural bias sneaks in under the radar. For example, in some cultures, attributing success to luck is a sign of humility. In others, it might signal a lack of confidence. If we’re not careful, we turn these interview moments into Rorschach tests, where what you see depends more on your expectations than on who the person actually is.

As a woman in leadership, I’ve seen firsthand how marginalized professionals often answer these kinds of questions differently. Not because they lack ambition, but because their path has taught them to be cautious, measured, and realistic.

So what are we really evaluating with this question, and whose worldview are we privileging when we evaluate it?

There’s a Better Way to Get to the Heart of It

If you’re a hiring manager or founder trying to assess a candidate’s attitude or worldview, here’s my take: skip the “trick” questions.

Instead, ask:

• Tell me about a time you felt everything was working in your favor. How did you handle that momentum?

• When things didn’t go your way, how did you interpret it?

• What role do you think luck, effort, and timing play in success?

These kinds of questions allow for context, reflection, and depth. They show you how someone makes meaning of their experiences, which is far more useful than whether they call themselves lucky.

Bring Humanity Back to Interviews

I get why people love these kinds of questions. They feel clever. They save time. They cut through the noise. And sure, sometimes they work.

But in a world where we’re constantly asking how to build more inclusive, equitable workplaces, maybe it’s time we retire the idea that a single question can reveal everything we need to know about a human being.

If you’re serious about hiring great people, don’t rely on “gotcha” psychology. Create space for real conversations. People are layered, and so are the forces that shape them.

So, are you a lucky person?

I’d rather ask how you define success.

Vivian Chen is the Founder and CEO of Rise, a trusted career platform and professional community for Millennial and Gen Z professionals, with over 5 million visitors, 80 million job views, and one of the largest career-focused newsletters in the U.S. A champion of diverse voices in the workforce, she also serves on the board of the Wharton Alumnae Founders & Funders Association and teaches marketing at Saint Peter’s University.