Many employers resort to the interview process to make a decision about a candidate. This is problematic because unstructured interviews provide surprisingly little useful information about future job performance. But, it doesn’t have to be that way as great interview questions can reveal so much
As an interviewer, your job is to gently get underneath the surface of the interviewee while creating enough psychological safety that the person can actually reveal who they are. Because let’s face it: a great candidate is interviewing you and your company as much as you’re interviewing them. The best interviews feel less like a test and more like a surprisingly meaningful coaching session. Occasionally, someone walks out thinking, “I learned something important about myself in there.”
Over the years, I’ve collected favorite interview questions that do exactly that. Some are mine. Some belong to other leaders and thinkers. All of them are designed to reveal not just competence, but character, self-awareness, adaptability, and wisdom.
1. “What’s the #1 way you’re misperceived in the workplace and why is that the case?” One of my favorites because it reveals self-awareness and emotional intelligence immediately. The answer often exposes the gap between someone’s intention and their impact—and whether they’ve reflected on it honestly.
2. “What’s a failure you’ve experienced that made you significantly wiser, and how have you successfully used that lesson since then?” Everyone says they learn from failure. This question helps you discover whether they actually metabolized the lesson into wisdom—or just survived the experience and moved on.
3. “What’s something you know now that you didn’t truly understand 10 years ago?” This question is really about evolution. I’m less interested in what someone knows than whether they’ve changed, softened, matured, or deepened over time and how that can continue in the future based upon a growth mindset.
4. “What’s a leadership philosophy that has your fingerprints all over it such that you could write a book about it? If you don’t have one, what leadership book has become your operating manual?” I love this because it distinguishes people who merely manage from those who lead intentionally. Leadership without philosophy means you’re at the whim of the latest management fad.
5. For compassionate people: “What’s the most selfish, courageous thing you’ve done that boosted your career or wisdom?” For ambitious people: “What’s the most selfless, altruistic thing you’ve done that boosted your company or career?” This helps reveal balance. Compassionate people sometimes need boundaries; ambitious people sometimes need generosity. Great leaders learn both languages.
6. Reed Hastings: “On your best day at work, what were you doing?” The co-founder of Netflix understands that joy leaves clues. This question reveals where someone naturally comes alive—and whether the role you’re hiring for matches their intrinsic energy.
7. Satya Nadella: “How do you bring out the best in others?” The CEO of Microsoft asks a deeply servant-leadership-oriented question. In a world obsessed with individual performance, this question reveals whether someone elevates the room or merely dominates it.
8. Indra Nooyi: “Who are you when things don’t go your way?” Former PepsiCo CEO Indra Nooyi understands that adversity is the great revealer. Anyone can look composed when the numbers are up and the applause is flowing.
9. Adam Grant: “What’s something you’ve changed your mind about recently?” This may be the ultimate curiosity question. If someone hasn’t changed their mind lately, they may be more committed to being right than to learning.
10. Peter Thiel: “What important truth do very few people agree with you on?” The famed entrepreneur and investor is testing for originality and intellectual courage. Safe thinkers rarely build extraordinary things.
In the end, great interview questions aren’t tricks. They’re invitations. Invitations into self-awareness, honesty, reflection, and possibility. The irony is that the very best interviews don’t just help you decide whether to hire someone. They help both people leave the room a little wiser than when they entered it.
-Chip