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.

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Prioritizing a candidate's skills ('capacity') over their fit with the team ('chemistry') is a mistake. To scale culture successfully, focus on hiring people who will get along with their colleagues. The ability to collaborate and integrate is more critical for long-term success than a perfect resume.

CEOs provide a curated view of their company's culture. To get an accurate picture, talk to people who have left the organization on good terms for an unfiltered perspective. Also, ask behavioral questions like 'What would you tell a friend to do to be successful here?' to uncover the real cultural DNA.

Duolingo lives by the mantra, "it's better to have a hole than an a-hole." The company spent 1.5 years searching for a CFO and rejected a candidate who was perfect on paper after discovering he was rude to a driver and a junior employee. This demonstrates a deep, costly commitment to protecting company culture.

Rituals like 'Waffle Wednesday' were not top-down mandates but organic traditions that fostered a family-like culture. This powerful culture became a self-correcting mechanism, quickly identifying and rejecting new hires who were selfish or not team players, often before management even noticed a problem.

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.

OnlyFans intentionally uses the "holiday dinner test"—asking candidates if they can defend their job to family—as a hiring tool. This filters for employees who are not just skilled but are "true believers" in the company's mission, ensuring extreme cultural alignment and resilience in their lean, high-performing team.

Ineffective interviews try to catch candidates failing. A better approach models a collaborative rally: see how they handle challenging questions and if they can return the ball effectively. The goal is to simulate real-world problem-solving, not just grill them under pressure.

When a CEO consistently emails on nights and weekends, it's a clear signal of a high-intensity work culture with low work-life balance. For candidates, this isn't just about the CEO's schedule; it's a cultural red flag or green flag depending on their own work preferences and expectations.

A powerful way to gauge cultural fit is to identify who is succeeding within the organization. Then, honestly assess if you respect them and their methods. If the path to "thriving" is paved by behaviors you don't admire, it signals a fundamental misalignment and may not be a game you want to win.