Rethinking the Engineering Interview

Ask almost any engineering leader about their interview process, and you’ll hear the same story repeated: technical puzzles, a handful of behavioral prompts, maybe a “gotcha” question for good measure. For years, I walked that path too. It’s the playbook everyone inherits—algorithmic whiteboard sessions, checklists of competencies, and boxes to tick off before the final thumbs-up.

But after sitting across from hundreds of engineers, something became impossible to ignore: the routines rarely reveal what actually matters. The best insights don’t come from clever riddles or canned “Tell me about a time” prompts. They show up in moments where the script falls away and you’re left with real conversation—where ambiguity isn’t a hurdle, but a window into how someone thinks.

The STAR framework (Situation, Task, Action, Result) has its place. But while it’s a staple for behavioral interviews, I’ve seen firsthand how traditional questions end up boxing candidates into rehearsed stories. The magic happens in open-ended conversations, where people don’t just recite—they reflect, adapt, and sometimes even surprise themselves.

If we want to spot talent that truly elevates our teams, we need to move beyond checklists and start asking questions that cut deeper.

What Makes an Interview Question Reveal Talent?

Not all questions are created equal. The ones that really surface signal—how someone thinks, learns, collaborates—share a few things in common: they’re open-ended, opinion-driven, and often deliberately incomplete. They leave space for the candidate to fill in the blanks, to show not just what they know but how they approach complexity.

I’ve seen this over and over. Closed questions—“Have you used Kubernetes?”—get you little more than a yes or no. Open-ended ones invite candidates to reveal their thought process, personality, and even their doubts. They help you see beyond technical skills to how someone might fit into your team’s culture and navigate real-world challenges. According to The Muse’s perspective on open-ended interview questions, these types of questions are essential for uncovering deeper insights during hiring.

Take backend engineering as an example. I once asked a candidate what frustrated them most about maintaining legacy systems. Their answer didn’t just highlight technical know-how; it revealed how they approached messy codebases—a challenge every engineering team faces eventually.

Let’s pause here: Compare “Describe your experience with Kubernetes” to “What do you like and dislike about Kubernetes?” The first invites a laundry list; the second asks for lived experience, nuance, tradeoffs. You start to see how someone actually works through ambiguity and uncertainty.

Kelly McGuinness at Electric nailed it: “Open-ended questions give you a front row seat into someone’s thought process and personality… The ability to answer quickly in a thoughtful way can show a lot of problem solving skills and give insight about how someone works behaviorally. It’s an opportunity for you to showcase your abilities and not just talk about what is on your resume.”

It’s tempting to default to safe scripts or technical trivia—it feels more objective. But if we stick too tightly to that formula, we risk missing what actually sets top performers apart: their ability to navigate gray areas, adapt on the fly, and engage in real conversation.

Key Questions That Signal Real-World Experience

The ‘Iceberg Model’ is handy here: what candidates say on the surface hints at deeper patterns—how they think under pressure or collaborate when things get messy. Open-ended questions help us look below the waterline.

Over time, I’ve found certain prompts consistently surface those authentic insights. Here are three that have changed how I assess engineering talent:

• “What do you like and dislike about [X]?”

  Don’t skip this one—it’s simple but sharp. Whether you ask about Tailwind CSS or Terraform, this question goes right to the heart of lived experience. Strong answers move beyond feature lists; they come alive with stories of frustration (“Debugging is a nightmare when…”) and appreciation (“I love how fast you can prototype…”). If someone’s worked with a tool in production, you’ll hear both sharp edges and wins.

  This is where you see if someone is dogmatic or pragmatic; if they consider multiple viewpoints or have real context behind their opinions. It’s one thing to recite documentation—it’s another to share war stories from the trenches.

• “Teach me something technical like I’m non-technical.”

  This one cuts straight through posturing. Instead of asking candidates to explain their communication style in theory (“Tell me about a time…”), just ask them to break down a tough concept for you—as if you had zero background. Can they read your cues? Adjust their metaphors? Check that you’re following?

  You learn not only what they know but also how they empathize with different audiences—a must for any engineer who works cross-functionally.

  It turns out that over half of top tech companies incorporate some variation of this ‘teach me something’ question in their interview process, according to Glassdoor data highlighted by ExpertBeacon. Meta has even replaced some traditional system design prompts with these open-ended teaching scenarios because they spark richer stories from actual experience rather than rote knowledge dumps; IGotAnOffer provides a detailed breakdown of Meta’s engineering manager interviews.

• Leave the question vague on purpose

  Sometimes I’ll simply say: “We’ve been running into issues with X lately. What are your thoughts?” No further details. The strongest candidates don’t lunge straight into solutions or buzzwords—they pause and ask clarifying questions: What kind of issues? When did they start? Who’s affected? They work their way into the problem space, showing curiosity instead of just confidence.

  That’s where real engineering happens: challenging assumptions, framing hypotheses, digging for context before diving in. Day-to-day work isn’t a string of neat problems—it’s messy systems needing thoughtful exploration.

If you’re interested in how engineers develop these skills outside of interviews—by learning to anticipate edge cases and think beyond rote algorithms—explore how proactive engineers solve unseen problems. That mindset is what truly shines through when candidates are given space for open dialogue.

From Ambiguity to Conversation: The Best Interviews

I’ll admit—I’ve wrestled with this urge myself: Stick to the script for fairness and consistency! But the best interviews? They rarely feel like interviews at all. They become working sessions where ambiguity isn’t an obstacle but an invitation.

This mirrors how great agile teams operate: ambiguity is embraced, iterative problem-solving is expected. In these interview moments, you see if someone freezes up when things aren’t tightly scoped—or if they lean in with curiosity and begin co-creating understanding.

For me, these sessions are microcosms of actual engineering work—full of gray areas and shifting priorities. The strongest candidates treat ambiguity as an opening: clarify context, build shared understanding, and work together toward solutions.

As interviewers, our job isn’t just to test knowledge; it’s to create space for dynamic exchange—to see how people navigate uncertainty together. That’s what high-impact teams do every day: not everyone knows everything up front, but everyone is willing to work through ambiguity as partners.

For further reading on how teams make smart decisions in uncertain situations—and why it matters for your interview process—see The Technical Decision Playbook: 7 Lessons for Smarter Engineering Choices.

Prioritizing Character Over Checklists

It’s easy—almost automatic—to fall into hiring for technical horsepower alone. We all want brilliant coders who breeze through frameworks or algorithms. But unless your team needs ultra-specialized knowledge right out of the gate, raw technical skill rarely tells the whole story.

From my own experience—and echoed by plenty of other leaders—the traits that elevate teams are much tougher to quantify: curiosity, humility, openness to feedback. You see these qualities not on résumés but in how candidates handle incomplete prompts or ambiguous scenarios. Are they willing to admit gaps? Do they ask thoughtful questions? Can they surface mistakes without going on the defensive?

A candidate who is opinionated yet genuinely open-minded—someone who can defend their views while welcoming input—will lift your team far more than someone who simply aces coding tests solo. Technical skills can be learned; collaborative character is much harder to teach later on.

Of course, consistency matters too—especially when comparing candidates fairly for the same role. Standardized questions make evaluation simpler, as Fellow.app advises. But standardization shouldn’t mean squeezing out everything human about the process.

As we rethink engineering interviews, let’s remember what makes teams thrive: not just what people know today but how they learn together tomorrow. The right questions don’t just evaluate skills—they invite conversation and reveal who people are when faced with uncertainty.

For another perspective on going beyond technical checklist interviews—and why moving past Leetcode-style grilling helps identify true engineering talent—consider reading Beyond Leetcode: Becoming a Better Engineer.

Closing Thoughts

The interviews that stick with me aren’t the ones where every question landed perfectly or every answer ticked a box. They’re the ones where both sides dropped the script—where conversation replaced interrogation and ambiguity sparked real collaboration.

The best candidates don’t just answer; they engage. And those are exactly the people you want by your side as you tackle complex realities together.

In the end, the questions we ask shape the teams we build. By inviting candidates into meaningful dialogue, we set a tone for curiosity and collaboration—a culture where both interviewer and candidate grow together. As you rethink your own interview process, consider what kinds of conversations will help your team thrive tomorrow—and take that first bold step.