Cracking the Behavioral Interview: What makes a story impressive?

If things went too smoothly you'll sound junior. Here's how to fix it.

Jul 28, 2025

It’s tempting to talk about your past work in a way that makes you look like you did everything right. The projects you prioritized were the obviously correct choice. Everyone immediately saw how good your solution was and supported it. Thanks to your amazingness everything went smoothly.

But, does that really make you sound impressive?

Imagine if a friend was telling you about a hike. They’d packed enough water, made no wrong turns on the trail, the weather was great, and their legs don’t even hurt. Do they sounds like a great hiker? Or does it sound like maybe they just picked an easy trail?

woman standing on mountain — Photo by Samuel Clara on Unsplash

You’d be more impressed if they made it sound harder. The weather was bad, the trail markings were confusing, it was slippery and steep, they almost gave up but pushed through.

The same idea applies to your interview answers, especially the ones where you want to show seniority.

The trick to sounding impressive is to show how hard the work actually was

You’re probably proud of your project because of how well it went. But instead of starting with everything that went well, you need to set up the contrast and make the interviewer believe that it could have gone really poorly.

It’s not easy to make your project sound hard, especially if you’re really good. You probably made a lot of good early choices that avoided problems later on. So here are some prompts to help you surface what was impressive about your work

What would a junior person have done differently?
What did you do differently than your boss expected you to do?
What aha moments or insights did you have?
Did your strategy or principles drive a decision?
What do you brag to your best friend about?

Let’s dig in.

What would a junior person have done differently?

Imagine someone less skilled had been in your shoes. Would they have done exactly what you did? If so, this isn’t a great story.

Think about how you might have handled the situation earlier in your career. Maybe you have some new best practices that you follow. Maybe you’ve learned more about your customer, the technology, or the industry that you used to make good decisions. Maybe you understood the importance of a factor that a more junior person would overlook?

What did you do differently than your boss expected you to do?

If you just did what your boss told you to do, that’s not very senior. What did your boss (or other leaders) think you’d do? What did you do differently? Why did they think the first idea was good, and why did you decide your approach was better?

Many of the best answers sound like “Everyone thought we should do X, but I realized we should do Y.” It makes it clear how easy it would have been to go with the flow, but you stepped up and steered in a better direction.

What aha moments or insights did you have?

If your idea was so good, why didn’t everyone already think it was the right choice? It’s probably because you saw something that no one else saw. Or you realized the importance of a fact that people were ignoring.

Often these insights come from watching a user, looking at data, listening to a talk, or trying to solve an intractable problem. Think about the times that it felt like the pieces fit together. Think about the times that you felt a conviction about the right path to pursue. What were the times when you thought “Wait a second…” and dug in?

Did your strategy or principles drive a decision?

Sometimes the most impressive things you did feel invisible to you because they’re just part of your internalized strategy or principles.

When we talk about seniority, a big part is the expertise that you've developed over the years. All the things you've seen, all the experiences you've had, all the conferences you've gone to, all the newsletters you've read, all of this comes together inside your brain leads you to good good decisions.

Maybe you have a principle to alway invest in usability, or that you need to serve basic users and power users, or that designs should be future-proof. Maybe your strategy was to move fast and quickly validate ideas, or to build strong partnerships. Maybe you believe that team morale needs to be addressed first.

Try to identify the strategies and principles behind your decisions and approaches. Can you remember when you first developed those strategies and principles?

What do you brag to your best friend about?

Getting gossipy can help you break through your internal censor that wants to be diplomatic.

A lot of us have a voice that says we shouldn’t brag, or we shouldn’t admit that our coworker was a real pain, or we shouldn’t talk about the sneaky way we got things done.

And to be honest, that voice is somewhat right - we can’t tell those stories as-is. But, once we’ve identified the impressive stuff we did, we can find more diplomatic ways to tell the story.

Practice

You can go through these questions alone, but if you get stuck, try going through them with someone friendly who knows your work. They might be able to point out the impressive things you did that you miss.

And if you prefer AI, I’ve got another custom GPT: Find the Impressive Parts of Your Story

Let me know if these ideas help!

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