
I always start with a structured, behavioral-based approach because past performance is the best predictor of future results. The first thing I ask is a variation of: “Can you me through a time when you faced a significant challenge at work and how you resolved it?” This forces candidates to tell a story with a clear situation, task, action, and result. I listen for specific details—not vague generalizations. If they say “I worked hard,” I press for numbers: “How did you measure that effort?”
I also ask about conflict resolution and adaptability because these are non-negotiable in any team. For example: “Describe a project where you disagreed with a colleague’s approach. What did you do?” The key is to see if they can collaborate without burning bridges. I avoid hypothetical questions like “What would you do if…” because they often lead to rehearsed answers. Instead, I rely on real past examples.
To keep the process fair and data-driven, I use a scoring rubric for each answer. Here’s a quick table of the three core areas I probe:
| Question Focus | Example Question | What It Assesses |
|---|---|---|
| Problem-solving | “Tell me about a time you had to make a decision with incomplete information.” | Analytical thinking, risk tolerance |
| Teamwork | “Give an example of a project where you had to persuade a resistant team member.” | Communication, influence, empathy |
| Self-awareness | “What feedback have you received that surprised you, and how did you act on it?” | Growth mindset, humility |
I also always ask candidates to describe their ideal work environment and compare it to our actual culture. This reduces mismatches and improves retention rates. Remember, a candidate’s answer to “What do you look for in a manager?” reveals a lot about their expectations. I’ve found that honesty about both strengths and weaknesses is a strong signal of maturity. If they only list positive traits, I gently probe for a real shortcoming. The goal isn’t to trick them, but to see if they can reflect honestly.
Finally, I leave time for their questions. The quality of their questions about the role, team dynamics, and company strategy tells me how invested they are. A candidate who asks “How does this role contribute to the company’s revenue goals?” is usually more engaged than one who asks only about vacation days.

I like to keep it simple and real. Instead of rehearsed questions, I ask: “What’s one thing you’d change about how your last team worked?” That catches people off guard and shows me their true thinking. I also ask about their proudest non-work achievement—it reveals passion and drive beyond the resume. If they fumble, it’s okay; I want to see if they can recover. I avoid long lists of questions. Just two or three genuine ones that dig into who they are, not just what they did.

From a strategic perspective, the most important question is: “What would you need to succeed in this role in the first 90 days?” This shifts the focus to onboarding and alignment. I also ask for a specific example of how they’ve learned a new skill under pressure because adaptability is critical in today’s market. Any candidate who can articulate a structured learning process—like breaking down the skill, practicing, getting feedback—is a strong hire. I avoid generic “strengths and weaknesses” questions—they’re too predictable. Instead, I probe for evidence of continuous improvement and resilience.

For a fast-paced startup, I ask: “If you joined our team tomorrow, what’s the first thing you’d want to change?” I’m looking for initiative and a fresh perspective, not just yes-people. I also love asking: “Tell me about a time you failed in public.” That shows vulnerability and honesty. If they can laugh about it and explain what they learned, that’s gold. I don’t use a script—I let the conversation flow naturally. A candidate’s energy and curiosity matter more than a perfect answer. I’ve hired people who bombed the first question but nailed the vibe.

I advise asking questions that uncover intrinsic motivation and cultural alignment. For example: “What kind of work makes you lose track of time?” This reveals their passion. Another favorite: “When you look back at your career, what’s the most meaningful project you’ve worked on and why?” The “why” part is key—it shows whether they value impact, learning, or recognition. I also ask: “How do you recharge after a stressful week?” to understand their self-care habits. A candidate who can’t answer that might struggle with burnout. Keep the tone warm and curious—you’re looking for a human connection, not a quiz.


