Chipotle CBO Chris Brandt filters candidates based on a simple, visceral question: 'Would you be willing to walk into a conference room with them at 5 PM on a Friday?' This test prioritizes collaborative spirit and cultural fit over pure skill, ensuring new hires won't disrupt team dynamics, even if they look good on paper.

The length of an interview can be a powerful diagnostic tool. A good, engaged candidate conversation should naturally last about an hour. If it ends in 15 minutes, the candidate is likely disengaged. If it stretches to two hours, they may lack the self-awareness to be concise. Use time as a simple filter for cultural fit.

The ideal early startup employee has an extreme bias for action and high agency. They identify problems and execute solutions without needing approvals, and they aren't afraid to fail. This contrasts sharply with candidates from structured environments like consulting, who are often more calculated and risk-averse.

Hiring for "cultural fit" can lead to homogenous teams and groupthink. Instead, leaders should seek a "cultural complement"—candidates who align with core values but bring different perspectives and experiences, creating a richer and more innovative team alchemy.

Injecting humor or pop culture references into interviews is not just for breaking the ice. It serves as a deliberate test for 'culture fit' by gauging a candidate's sense of humor, which strongly correlates with desirable traits like flexibility, curiosity, and friendliness that are difficult to assess directly.

Counterintuitively, being brutally honest with candidates about the low odds of success is a powerful recruiting filter. It selects for mission-driven individuals who are mentally prepared for the inevitable tough cycles of a startup, ensuring they won't quit when things get difficult.

To clarify difficult talent decisions, ask yourself: "Would I enthusiastically rehire this person for this same role today?" This binary question, used at Stripe, bypasses emotional ambiguity and provides a clear signal. A "no" doesn't mean immediate termination, but it mandates that some corrective action must be taken.

The common practice of hiring for "culture fit" creates homogenous teams that stifle creativity and produce the same results. To innovate, actively recruit people who challenge the status quo and think differently. A "culture mismatch" introduces the friction necessary for breakthrough ideas.

Ditch standard FANG interview questions. Instead, ask candidates to describe a messy but valuable project they shipped. The best candidates will tell an authentic, automatic story with personal anecdotes. Their fluency and detail reveal true experience, whereas hesitation or generic answers expose a lack of depth.