Hiring Managers, Are You Asking the Right Questions in Your Interviews?
Hiring Managers, Are You Asking the Right Questions in Your Interviews?
Why Most Interviews Suck
Ah, the job interview—the place where candidates pretend they're perfect, and hiring managers pretend they know what they’re looking for. It's like a high-stakes speed-dating event, except instead of gauging chemistry over cocktails, you're sifting through rehearsed answers and resumes polished to a gleam. You ask the same questions you’ve been asking for years, and guess what? You're getting the same mediocre results.
Here's the dirty secret: most hiring managers have no idea what they're doing when it comes to interviews. They rely on outdated, rote questions like "What's your biggest weakness?" or "Where do you see yourself in five years?"—questions that should've been retired along with dial-up internet and AOL instant messenger.
This essay isn’t a “how-to” manual. It’s a cold, hard look at why so many interviews fail to uncover what really matters—and why the best questions are the ones that reveal what candidates don’t want you to know. Spoiler: If you're not sweating by the end of an interview, neither of you have done your job right.
Why Most Interviews Suck
Let’s start with the basics: the traditional interview structure is broken. The whole process reeks of performative theater, with candidates playing the role of “Ideal Employee” and interviewers pretending they're psychic, basing hiring decisions on gut feelings or vibes.
Most hiring managers assume they're good at interviews because they've done hundreds of them. But here’s the kicker: you can conduct thousands of interviews and still be clueless. The real question is, have you been asking the right questions? Or are you just cycling through a checklist that would bore a kindergartner?
Hiring is high stakes. Yet we treat the process like it's a trip to the DMV: dull, repetitive, and utterly devoid of humanity. Here's why you should care: the cost of a bad hire can be astronomical. According to the U.S. Department of Labor, a bad hire can cost up to 30% of that employee's first-year earnings. In simpler terms: screw up once, and you’re lighting tens of thousands of dollars on fire. This isn’t just about dollars and cents, though—it's about company culture, productivity, and momentum.
So, what do most interviews do wrong? They focus on hypotheticals rather than reality. Asking someone how they'd handle a situation ("Tell me about a time you...") isn’t as powerful as asking them about their real, tangible accomplishments. Hypotheticals invite fluff; reality demands evidence.
The Overrated, Overused Questions
Let’s walk through a few classic interview questions that are about as useful as a screen door on a submarine:
"What's your greatest weakness?" Really? People still ask this? I’m shocked every time I hear it. Candidates prepare canned responses like, "I work too hard" or "I care too much." The real answer should be, "My biggest weakness is having to listen to this tired question for the hundredth time." This question is a waste of breath. You want to know someone's weaknesses? Ask them what they’re working on right now to improve. That’s a lot more revealing than some faux-self-deprecating nonsense.
"Where do you see yourself in five years?" In five years? Hell, half the time they’re trying to figure out if they’ll still want to work for your company in five months. This question doesn’t get you insight into ambition or strategic thinking—it just gets you a rehearsed answer about climbing the corporate ladder or "being in a position to help the company grow."
"Why should we hire you?" If you're asking this question, you’ve already failed. You’re essentially admitting you haven’t done your homework. You’re fishing for a soundbite that fits your preconceived notion of what the right candidate should say. Instead, you should be able to tell the candidate why you’re interested in them. If you can't, you probably shouldn't be hiring them.
The Right Questions: Cut the Bullsh*t
So, what should you be asking instead? Interviews are about uncovering the truth. Not the truth candidates want you to see, but the gritty, often hidden reality that reveals their true potential—or lack thereof.
"Tell me about a project that went sideways and what you did to course-correct." Everybody has failed at something. This question doesn’t just tell you how they handle failure; it gives you a window into their problem-solving skills, resilience, and accountability. Did they take ownership, or did they point fingers? This question cuts through the B.S. and tells you how they respond when things get real.
"What skill do you have that you think is undervalued in most workplaces?" This question reveals a lot about how self-aware the candidate is, but it also opens the door to understanding their value system. Do they think being a good listener is important? Do they emphasize adaptability, empathy, or creativity? The answer also shows how they might fit—or not fit—into your team’s dynamic.
"If you could change one thing about your current role, what would it be and why?" This question gives you a sense of what frustrates them and where they see inefficiencies or missed opportunities in their current environment. It also gives you a sense of whether they’re solution-oriented or just complainers.
"What’s the most uncomfortable feedback you’ve ever received?" Anyone can talk about success, but how do they handle criticism? If they stumble through this one or provide a weak answer, that’s a red flag. You want someone who can take feedback, process it, and come out stronger on the other side.
"What’s something you’ve taught yourself in the past year?" The world is moving fast, and if you’re hiring someone who hasn’t upskilled or learned something new recently, you’re hiring dead weight. This question digs into their capacity for self-improvement and intellectual curiosity—two qualities you want in spades.
Beyond the Questions: Focus on the Conversation
The best interviews feel less like an interrogation and more like a dialogue. You should be probing deeper, pulling on the threads that the candidate lays out for you. This means active listening, following up on answers, and asking for specifics. If they tell you they led a team that launched a new product, ask for the exact metrics. What was their role? What challenges did they face? What would they do differently next time?
Interviews shouldn’t be a one-size-fits-all approach. If you’re hiring for a creative role, your questions should force them to think outside the box. If you’re hiring for a technical position, you need to drill down into specifics about their technical acumen. But regardless of the role, every interview should be a fact-finding mission where you get a sense of not just the candidate’s skills, but how they approach problems, interact with others, and—most importantly—how they think.
Beware of Cultural Fit
Ah, “cultural fit.” It’s the catch-all phrase for, “I don’t know why, but I just didn’t like them.” Cultural fit is often where bias creeps into the process. You’re more likely to hire someone who looks like you, talks like you, and likes the same things as you under the guise of “fit.” But here’s a novel idea: maybe your culture could use some shaking up.
Instead of focusing on whether the person fits into your current culture, ask yourself this: "Does this person bring something new to the table?" What perspective are they adding that you’re missing? Homogeneity might make for a comfortable work environment, but diversity makes for a better one—better ideas, better problem-solving, and better results.
The Final Interview Question: "How Will This Person Make My Team Better?"
At the end of every interview, there’s one question every hiring manager needs to answer: "How will this person make my team better?"
It sounds simple, but it’s the crux of the entire interview process. You’re not just hiring a warm body to fill a seat. You’re hiring someone who’s going to push your team forward. If you can’t answer that question confidently after an interview, it’s a red flag. It means you’re still unsure of the candidate’s value—and if you’re unsure, it’s time to move on.
The best hires don’t just fit—they elevate. They bring something to the team that’s been missing, whether it’s a unique skill set, a fresh perspective, or simply the drive to push the team to new heights.
The Real Cost of Bad Hires
We’ve all been there: you hire someone you think is going to be a rock star, only to realize six months later that they’re barely treading water. Every bad hire is like throwing a wrench into a well-oiled machine. The cost isn’t just monetary—it’s about the time wasted, the damage to team morale, and the disruption to your company’s momentum.
Studies show that bad hires can cost companies anywhere from $25,000 to $50,000, and that’s just the financial hit. The bigger loss is in the opportunity cost—what could your team have accomplished with the right person in that seat? The wrong hire doesn’t just slow you down; they can set you back.
Interviews Should Be Challenging—For Both of You
Here’s the truth: a great interview should feel a little uncomfortable. If it feels too easy, you’re probably not asking the right questions. You want to push candidates to think critically, to reflect on their experiences, and to reveal who they really are—not who they think you want them to be.
And it’s not just about challenging the candidate. You, as the hiring manager, should be challenged too. You should leave the interview with a clearer picture of what your team needs, not just whether the candidate fits some preconceived mold.
Final Thought: Stop Asking, Start Listening
Here’s the final kicker: interviews are more about listening than asking. The best hiring managers know when to shut up and let the candidate speak. They know when to dig deeper and when to step back. They understand that the real magic happens in the conversation, not in the questions.
So, hiring managers: are you asking the right questions? Probably not. But here’s the good news—it's not too late to change that.
Hi there, it’s me, Brian, and in addition to this Substack Newsletter, I’m writing the proverbial (no surprise here) sequel to Talk Tech To Me. I take on the stress and strain of complex technology concepts and simplify them for the modern recruiter. Pick up your copy today.