Culture Interview Questions Reveal Alignment
by Chip Conley on August 3, 2025
When evaluating company culture during interviews, ask strategic questions to uncover the true environment before committing to a role.
The interview process is a two-way evaluation - you're assessing the company as much as they're assessing you. To effectively gauge culture fit (or better yet, your potential to "culture add"), use these targeted questioning techniques:
Strategic Culture Assessment Questions
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Ask multiple interviewers: "What are 3-5 adjectives that define this culture?"
- Listen for consistency across different respondents
- Inconsistent answers may signal misalignment or departmental culture variations
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Probe for problems: "What's the biggest problem in this culture that's endemic across the organization?"
- Follow up with: "Is it ever going to get fixed?"
- For more senior roles: "How could I come in and help address this issue?"
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Pay attention to departmental variations
- A team or department can have a distinct subculture within the broader company
- In the long run, the overall company culture will exert "oppressive influence"
- Even great departmental cultures may struggle within a problematic company culture
Why This Matters
This approach helps you:
- Identify misalignment between stated values and actual practices
- Determine if there's consistency in how the culture is understood
- Assess whether cultural challenges are acknowledged or hidden
- Evaluate if you can thrive in this environment or contribute to its improvement
The questions reveal not just what the culture is, but how self-aware the organization is about its strengths and weaknesses. This insight is crucial because culture ultimately determines "what happens around here when the boss is not around" - especially important in distributed or remote work environments.