Not long ago, a client came to us looking for an Operations Director. They had already identified a candidate they were excited about before we even became involved. On paper, he looked like exactly what they wanted, and the first interview went well.
The hiring team felt fairly confident, but before extending an offer, they asked us to conduct a more in-depth interview — one focused on exploring how he led people, handled conflict, and navigated difficult situations. And that’s when things changed.
Tech-Driven Hiring vs. Listening to How They Think
Hiring has changed dramatically over the last few years. AI tools can assist candidates in writing polished resumes, optimize LinkedIn profiles, and even prepare answers to common interview questions. Technical skills can be verified, references can be checked, and resumes can be tailored to almost any job description.
Ironically, as candidates become better at presenting themselves, interviewing has become more difficult. Many hiring managers have never learned how to interview effectively. Instead, they rely on instinct and impressions, but that can favor smooth communicators and leave gaps.
When we interviewed that Operations Director candidate, we asked him about complicated moments as a leader:
- Tell us about a time a direct report challenged one of your decisions.
- Tell us about a project that didn’t go as planned and what would you do differently today?
- What is the toughest feedback you’ve ever received and did you agreed with it?
The answers weren’t necessarily wrong, but a pattern quickly emerged: every difficult situation seemed to be someone else’s fault. We didn’t hear much ownership, reflection, or self-awareness.
When we shared our observations with the client, they paused. Those weren’t things they had picked up in their own interviews because they had spent most of their time validating technical experience rather than exploring how the candidate actually operated as a leader.
The client decided to continue interviewing.
The person they ultimately hired had a less impressive resume and came from a smaller organization, but there was a noticeable difference in how he talked about challenges. He openly discussed mistakes he’d made, lessons he’d learned, and how those experiences shaped his leadership style.
A year later, the client told us it was one of the best leadership hires they’d made.
Stop Looking for the “Right” Answers
The strongest interviews often feel less like interrogations and more like conversations. One of the biggest mistakes we see is asking questions that invite rehearsed responses.
- “What are your strengths?”
- “Tell me about a challenge you overcame.”
- “Where do you see yourself in five years?”
Most experienced candidates have answered these questions dozens of times. Instead, ask questions that require reflection rather than preparation.
- Tell me about a time you received difficult feedback. What did you do with it?
- What’s a decision you made that you’d handle differently today?
- Describe the best manager you’ve ever worked for. What made them effective?
These conversations reveal something a polished resume never can: self-awareness. Listen for how they approach problems. Can they explain their reasoning? Take ownership of mistakes? Disagree respectfully? Do they demonstrate genuine curiosity?
The Bottom Line
Technical skills can get someone hired, but how they think determines whether they’ll truly succeed.
And remember: every interview is a reflection of your company. Over the past year, we’ve noticed candidates are evaluating employers just as carefully. A disorganized or unclear interview process can cause great candidates to question the organization itself.
Because technology has made it easier than ever for candidates to present themselves well, the human side of hiring is more important than ever. When you create a real conversation, you come to understand the person sitting across the table – and that’s what drives the most successful hires.
