Alright, let’s talk about interviews. Because honestly? I used to hate them. Picture this: Fresh out of community college, wearing a too-tight blazer from Target, sweating through my third Starbucks latte while waiting to interview for a sales job. The hiring manager asked me, “Where do you see yourself in five years?” and I blanked so hard I said, “Uh… managing a Starbucks?” (Spoiler: Didn’t get the job.)
Fast-forward five years and 100+ interviews later — both as the nervous candidate and the exhausted hiring manager at a mid-sized tech startup — and here’s what I’ve learned: The best questions aren’t about tricking people. They’re about peeling back layers.
The “Secret Sauce” Nobody Talks About
Early on, I thought memorizing “correct” answers was the key. Wrong. At my first hiring gig, my boss (a gritty New Yorker who’d built her career in the ‘90s) told me: “If someone’s rehearsed, they’re hiding. Ask them something messy.”
So I started testing real-life scenarios instead of textbook ones. One question that’s gold:
“Tell me about a time you had to fix something without asking for help. How’d that go?”
You’d be shocked how this separates the “I’ll figure it out” folks from the “I need hand-holding” crowd. One candidate admitted they accidentally deleted a client’s database — then stayed up till 3 AM rebuilding it from scratch. Hired ‘em on the spot.
The Two Questions That Changed Everything (For Me)
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“Walk me through your resume, but skip the job titles. Tell me why you left each role.”
- People freeze here — and that’s the point. You learn fast if someone’s running toward growth or away from conflict. One guy straight-up said, “My boss was a micromanager, and I’m allergic to babysitters.” We high-fived.
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“What’s a hill you’d die on at work?”
- Stole this from a HR guru at a Denver startup conference. Answers range from “I’ll fight for 15-minute stand-ups instead of hour-long meetings” to “Free office snacks are non-negotiable.” It reveals values fast.
When You’re the One Sweating in the Chair
After bombing that Starbucks interview, I begged a mentor for help. She grilled me with:
- “What’s the dumbest mistake you’ve made at work, and why would we want you to make it here?”
- “If I called your last boss right now, what’s the first thing they’d say about you?”
Pro tip: Answer honestly, but pivot to growth. Example: “They’d say I ask too many questions. But last quarter, those questions helped us dodge a $10K tech error.”
The Uncomfortable Truth About “Good” Answers
Here’s the kicker: Authenticity beats perfection. I once hired a woman who admitted she Googled “Python basics” before our coding interview. Her hustle impressed me more than the guy who recited textbook algorithms.
And if you’re stuck prepping? Do this:
- Research the interviewer’s LinkedIn. Find a shared interest (mine’s horror movies — thanks, Hereditary).
- Practice telling stories, not stats. Use the “CAR” method — Challenge, Action, Result.
- End with: “Is there anything about my experience that makes you hesitant?” It’s like ripping off the Band-Aid.
Wrapping Up Like a Human
Look, interviews are awkward first dates. You’re both trying not to spill coffee while figuring out if this is a fit. My last nugget? Send a follow-up email referencing something personal from the chat. After my current job interview, I wrote, “Still thinking about your raccoon-in-the-office story. Hope HR approves pest control!” Got the offer the next day.
Now go dust off that blazer. And maybe switch to decaf.
(P.S. If you bomb one? Congrats — you’ve got a story for next time. Ask me about the Zoom call where my cat attacked the webcam.)