The 9 Interview Questions You Can Never Ask — But Would Tell You Everything
Let’s be honest — the “Tell me about a time when…” interview questions are as old as the Reagan administration and about as useful as a flip phone for taking a picture.
They’re rehearsed, predictable, and they rarely tell you who someone really is. If you’re hiring, managing, looking to level up — or just trying to live with more discipline and grace — it’s time to look beyond the script.
The best indicators of success, leadership, and integrity often show up in the places no one’s asking about — habits, routines, awareness, and how someone moves through everyday life.
These questions are technically off limits — but they’re the ones that would tell you everything.
9 interview questions you can’t ask — but everyone should consider asking themselves.
1. What did the first three hours of your day look like?
Why we’re asking: What happens between 5 and 8 a.m. tells us more than a resume. Movement, reflection, planning, even quiet — it's about showing up for your life with intention. Leaders tend to start early, with structure. Chaos in the morning usually leads to chaos all day.
2. How much money do you have?
Why we’re asking: Show me someone who doesn’t know their finances, and I’ll show you a life falling apart — or one decision away from it. If money can buy happiness, then not knowing where your money is buys misery by the pound. The question isn’t about the number — it’s about awareness. Cash flow, debt, emergency fund, credit utilization, retirement accounts. Do they know where they stand? If someone is leading your organizational budget, they should first know how to lead their own.
3. What’s your retirement strategy?
Why we’re asking: A teenager on TikTok today has more financial literacy than many department heads managing multi-million-dollar budgets. How someone prepares for retirement reflects how they’ll plan for your organization’s long-term goals. We’re looking for specific age goals, investment diversification, and contingency planning. Bonus points if they’re involved in the portfolio.Double bonus points if they’re not deferring the whole retirement plan to a spouse or financial advisor. Leadership isn’t passive. And how people plan their retirement a part from a beach somewhere, someday, speaks volumes about their financial accumen.
4. What’s dinner during the week look like?
Why we’re asking: Is food and nourishment a time for family, conversation, gratitude — no devices, maybe a good book nearby? Or is it mindless eating in front of the TV every night? Or blowing money on eating out? We’re not judging — we’re observing. Because how someone eats reflects how they value time, care for themselves, and show up with presence or detachment. It may sound harsh. Yet, I can look back to my own time of chaos and not meal planning or having family meals is a first domino to other bad decesions.
5. What’s your favorite piece of art, book, or music?
Why we’re asking: The things that move us, shape us. They also reveal how someone expands their world. Are they curious? Are they reading, listening, learning, and reflecting?
In the spirit of Mother’s Day, my favorite piece of art is a still life of flowers by Jan Van Huysum, which I first saw with my mother, Sandra. We were at the Getty Museum in Los Angeles. She later bought the print and had it beautifully framed for me. It hangs in my home, or sometimes you may see it during a Zoom meeting behind me. It’s a reminder of beauty, memory, and the quiet strength that we pass down through small gestures. (Ask this question and you’ll learn volumes about the other person, I promise).
Having a favorite piece of art, book, song, or movie is something to share and to be inspired by.
“Bouquet Of Flowers In An Urn, 1724 " by Jan Van Huysum
6. Can you give me a ride?
Why we’re asking: Someone’s car tells you who they are when no one is watching. Is it clean? Gas tank full? Windows clear? Or is it a mess of old receipts, wrappers, and burnout?
One of my first clients was a Critical Access Hospital in the foothills of California. I was driving up to meet with the Board for a CEO search, and my mother told me — “Clean your car.” I had three small children and was already fairly tidy, but she was pointed in her direction. I cleaned that car, washed it twice, and even treated the leather. It looked good and smelled even better. It was a proud moment driving up to the hospital.
I arrived, ready to impress. And, as if my Mother knew, the HR Director looked at me and said, “Let’s go meet the Board Chair for lunch before the meeting — can you drive?”
7. I’d love to invite you to tomorrow’s Legacy Ball — it’s semi-formal.
Why we’re asking: Can someone pull it together and show up well, even on short notice? It’s not about having an expensive suit or designer dress— it’s about being presentable, confident, and proper for the occasion. Do you get a haircut before you need it, or when it’s overdue? Being ready to dress up, smile, extend a manicured hand, and hold a conversation with confidence shouldn’t take a day and a pit crew to prepare for. People who take pride in how they leave the house tend to take pride in their work, too.
8. What was the worst part of your last job?
Why we’re asking: Everyone has an answer — it’s how they tell the story that matters. Are they stuck in blame, or do they show growth and insight? Do they see challenges as defining moments or just complaints? Leadership reveals itself in hard seasons, not just on good days.
9. Can I see your phone?
Why we’re asking: Patterns tell a story. What are the last 10 videos they liked? What tone do they use in comments? Are they curious and kind — or angry and opinionated? What apps are they starting and ending their day with? A person’s phone reflects their mind, priorities, and peace. (Taking a look at your own is a great self-check-in.)
The Bottom Line:
These aren’t questions you can ask in a formal interview, but the answers are everywhere if you know where to look.
If you’re hiring, growing, or just trying to be a better human being — pay attention to how people live.
And more importantly, pay attention to how you live.
You don’t need a title to be a leader. You need intention, follow-through, and the courage to live a little better — every single day.
Enjoy the week.
Nicole Barbano - Founder and Principal | Hunter Ambrose Int.
