Co Founder | Marketing Strategist | Podcast Host at Ctrl+Hire

Let’s be honest, most interviews are broken.

We obsess over performance, polish, and pedigree… and completely miss the person sitting across the table.

After conducting over a hundreds of interviews across functions, roles, and industries, here’s the one thing I’ve learned:

Great interviews aren’t about catching people off guard. They’re about discovering who they are how they think, what they value, and whether they’ll thrive in the role and culture you’re hiring for.

So what kind of questions actually help you assess that?

Here’s my honest guide.

1.

"Tell me the story behind this resume."

Don’t just go line by line. Ask for the story, the pivots, the leaps of faith, the detours. This gives you context, intent, and self-awareness in one go.

2.

“I’m giving you two choices. What do you pick and why?”

I often give candidates ethical or practical dilemmas. Not to test morality, but to map their values, do they prioritise ownership or harmony? Speed or perfection? Risk or process?

This gives you a fast track into their decision-making DNA.

3.

“Here’s a real-world mess. How would you tackle it?”

Case studies don’t need a fancy deck. Sometimes I’ll just throw a problem like:

“You’re managing two interns one’s brilliant but arrogant, the other’s slow but eager. The project is time-sensitive. What do you do?”

This helps me assess three things:

• Prioritisation: What needs to happen now vs. later

• Communication: How clearly they explain their approach

• Delegation: Whether they think like a lone wolf or a team player

4.

“How would you rate this interview?”

One of my favorite closers. It reveals humility, self-awareness, and even their sense of humor. Some get defensive. Some are reflective. A few will ask me for feedback in return, those are usually keepers.

5.

“What’s one thing your last manager misunderstood about you?”

Great for surfacing emotional intelligence, conflict patterns, and how they see themselves. You’ll learn more from this than asking, “What are your strengths?”

6.

“What are you hungry for?”

Skills can be taught. Tools can be trained. But hunger, that’s a trait. The best hires I’ve made weren’t always the most polished. But they were hungry. They had something to prove. And when guided right, they did wonders.

7.

Watch for this red flag: Shortcut-seeking.

If I sense that someone’s constantly looking for the “hack” or “bare minimum,” it worries me. That’s not optimization, that’s a mindset that often bleeds into ethics, effort, and ownership.

Also, if someone reschedules interviews multiple times or shows up late, it’s not a logistics issue. It’s a signal.

8.

Look for this green flag: Grit with gratitude.

Some candidates quietly carry a chip on their shoulder, not from entitlement, but from lived experience. They’ve struggled, stretched, and shown up. That combination of hunger and humility? Gold.

9.

Build your own model. Here’s mine:

HAD Framework

• Hunger – Do they want it bad enough?

• Attitude – Are they coachable, collaborative, curious?

• Decision-making – Can they think on their feet and stand by a choice?

10.

Always remember:

Spend time on the resume to understand the person.

But spend time with the person to understand their potential.

TL;DR?

Interviews aren’t auditions. They’re discovery missions.

You’re not just hiring a skillset. You’re investing in a human being.

Ask better. Listen sharper. Hire wiser.