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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

  • 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
  • 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?"
  • 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.