Tell me about a time when…

Interviewing? Whether you’re hiring or job hunting, the questions you ask can make or break the conversation. Most people ask the wrong ones—here’s how to do it better.

The Employer

Here’s a typical interview question an employer might ask: “Tell me where you see yourself in 5 years.”

Everybody hates this question. It requires the candidate to make something up when they are right now focused on the next few months of getting a job where they can be happy, do well, and pay their bills. Or it requires them to hold something back like, “Running these interviews”, “In your job”, or “As your boss”. Or maybe running their own business, going to their dream company in another job, or changing careers. In any event, it doesn’t give the employer great information to make a better hiring decision.

If you’re tempted to ask the 5-year question, pause and ask yourself: What do I really want to know?

If you’re assessing ambition or stability, try these instead...Is it to get a better read on their ambition. Or is it to see how long they might stay and assess their stability? Consider trying questions like these to be more specific to the traits and behaviors you are trying to assess. “Can you tell me about a time when you really went for it or stretched yourself when you wanted something?” Or, “Can you tell me about a time when you were the steady one in the midst of chaos or rapid change?”

Not only are these more specific and aligned to what you’re trying to figure out, these will give the candidate an opportunity to share a story with you, something that actually happened.

The Employee

Interviews are a two-way street. A great question doesn’t just help you learn about the role—it shows the employer that you think strategically.

Here’s a typical interview question an employee might ask: “What does a successful candidate look like for this role?” This is a better question than the 5 year question because it focuses in on more relevant and crucial information, but we can still do better.

If your goal is to learn more about what has made people more successful (and unsuccessful) in the roles you are considering, you might want to try a questions like this. “Can you tell me about the last candidates you hired in this position who one, really crushed it in their first few months, and two, who flamed out and ended up moving on?”

This question will give the employer an opportunity to tell stories about what led to success for the first hire and what didn’t for the second hire. You can then consider how close each of these candidates is to the way you work, as well as the expectations of the employer and how well those align with yours.

Hypotheticals vs. History

You see, when people are given hypotheticals, they often know what the “right” answer is. And since the question is being asked in a hypothetical way, it’s easy to make things up. They want to give the “right” answer. And the hypothetical answer doesn’t allow them to share as much about themselves.

But when people are asked about the past, they tend to share what they remember without trying to frame it too much as the “right” answer, and they aren’t tempted to make as many things up.

People can fake a perfect answer—but they can’t fake their past. Asking for real stories gives you the truth, not just what they think you want to hear.

Real stories are also an opportunity for people to share something that didn’t work and what they learned from it. This gives them the opportunity to say what went wrong, that they wouldn’t handle it that way again, and what they would do differently next time.

“What did you learn from that experience?” is another great prompt if they don’t immediately offer that up in their answer. It can help elicit those learning kinds of responses and demonstrate an open mind and growth mindset.

Next Steps

Get away from the generic and the hypothetical. Start asking for stories and past experiences.

You’ll find that even though you might ask the same question of 5 different people (candidates and employers both) that the answers are all different. And they’re more revealing about the individual in front of you, helping you make better decisions around alignment and fit.

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Struggling to hire the right people? Or looking for your next great role in rehab therapy? Let’s chat—message me to get started.