This is Scale & Strategy, the newsletter that catches you up like a blue shell in Mario Cart.
Here’s what we got for you today:
The Best Interview Questions We've Ever Published
Over the years, we’ve gathered standout interview questions from leaders across every discipline. These are the ones that consistently reveal top performers and help you hire people who actually elevate the team.
Why This Matters
Hiring is still the most painful, high-stakes problem founders deal with. One wrong hire can snowball into lost time, lost momentum, and lost sanity. Most experienced CEOs will tell you early-stage founders should spend half their time recruiting. And yet, even with frameworks and rubrics, interviewing remains more art than science.
Your questions are the leverage point. You only get a narrow window with each candidate. Every minute needs to extract insight.
This collection pulls together the most effective questions we’ve heard, including deep dives into interviewing for technical and product roles. Think of it as the definitive shortcut to running interviews that actually work.
We also recently crowd-sourced even more favorites from operators in our network.
1. Questions That Reveal the 7 Core Traits of High Performers
Kristen Hamilton, Co-founder and former CEO of Koru, has spent years placing early-career candidates into roles where they thrive. Her work led to one clear conclusion: seven traits consistently predict strong performance, regardless of role or seniority:
Grit
Rigor
Impact
Teamwork
Ownership
Curiosity
Polish
She pairs each trait with a targeted question:
Grit Tell me about a time you wanted something badly enough that you refused to give up. What obstacles did you overcome? Listen for duration and persistence, not theatrics.
Rigor Tell me about a time you used data to make a decision. Look for how they thought, not whether they landed the “right” answer.
Impact
Tell me about a time you had a measurable impact.
Tell me about someone or an organization you admire and why their impact matters. You’re looking for an ability to think in trade-offs and outcomes.
Teamwork
What’s hardest for you when working on a team?
Tell me about a difficult team experience and describe it from the other person’s perspective.
What makes you happiest and most effective when working with others? This is an EQ test disguised as a conversation.
Ownership Tell me about a time you experienced something unfair. True owners acknowledge the unfairness but don’t wallow in it.
Curiosity What’s the last thing you really geeked out about? You want to hear about obsessive self-directed learning.
Polish
Observe how they handle interruptions.
Notice whether they send a thoughtful thank-you note. You’re watching for calm professionalism under pressure.
2. The Anatomy of a High-Signal Technical Interview
Neil Roseman, former VP of Technology at Amazon and Zynga, has run hundreds of interviews. His view: a great technical interview is intentionally designed to dig into actual accomplishments, decision-making, and leadership potential.
What strong questions do:
Probe: Give me an example…
Dig: who, what, where, when, why, how
Differentiate: participant vs. owner, exposure vs. expertise
Roseman leans heavily on Behavioral Interviewing, anchored in STAR (Situation, Task, Actions, Results):
What was the context?
What were you responsible for?
What actions did you take?
What were the measurable results?
His favorite universal soft-skill question: Do you consider yourself lucky? He’s looking for people who create their own “luck” by staying prepared and opportunistic.
For business operators scaling from $1M to $10M, leverage is everything. AI can automate, but it can’t anticipate, contextualize, or build trust.
The smartest operators already know: the future isn’t AI-only. It’s AI paired with capable, strategic human support.
That’s the idea behind our latest guide: The 5 Traits AI Can’t Replace & Why They Matter More Than Ever. A fast, actionable read for business operators who want to scale with clarity — not just speed.
And when you're ready to put those traits into action?
BELAY matches you with U.S.-based Executive Assistants who bring judgment, initiative, and relational intelligence to your business — not just task management.
Anne Dwane (Zinch, Chegg, Village Global) believes adaptability is the defining trait of great startup leaders. Adaptable people surround themselves with other resourceful, high-learning-velocity teammates.
She anchors her interviews in questions that surface self-motivation and continuous learning:
What motivates you, and what do you want to do next?
What have you started?
How would you describe yourself?
How would colleagues describe you in three adjectives?
What trends are you seeing in your field?
What new things have you tried recently?
She also gives candidates a presentation assignment on a topic they care about. If they dread it, that’s your red flag.
4. Questions Built to Block Bureaucracy Before It Starts
Mike Curtis, former VP of Engineering at Airbnb, has seen how slow-creeping bureaucracy can cripple a company. His solution: hire people who don’t require heavy process to perform at a high level.
Airbnb allocated an entire 45-minute interview to culture and character. That session had four key moves:
1. Let them shine first. Have them walk through a project they’re proud of. You’re mapping what energizes them.
2. Then introduce discomfort. Ask about moments where they disagreed with leadership or had to cut corners under pressure. Watch how they react: blame, deflection, collaboration, ownership.
3. Calibrate as a team. Standardize interview scoring by reviewing packets together. Make subjective judgments less subjective.
4. Beware of coaching. If they start parroting your internal language, they might be coached. Not fatal, but worth noting.
5. How to Hire Originals
Wharton professor and bestselling author Adam Grant studies “originals”: creative, principled contrarians who can reshape organizations.
His go-to questions:
1.Tell me about a rule in a past organization that made no sense. What did you do about it? You want someone who investigates, gathers context, builds allies, and improves the system without blowing it up for sport.
2.Why shouldn’t I hire you? Strong answers show self-awareness and a differentiated value proposition, not self-sabotage.
3.In your first few months here, what questions would you ask and to whom? Originals ask questions others overlook and seek out non-obvious sources.
4.How would you improve our interview process? You’re looking for thoughtful critiques and creative solutions that show they understand how organizations actually work.
