Interview Questions

The 15 Best Interview Questions for a Head of People & Culture

By Maya Kosoff

Last updated: Feb 15, 2023

Whether you’re looking for a new job at a startup’s People team or trying to hire a Head of People, we’ve collected more than a dozen potential questions to keep in mind before the interview process.

No matter the size of your company, hiring an exceptional Head of People & Culture is important. This is the person who will future-proof your startup against organization issues, help set the tone culturally and act as a renaissance person. The right Head of People oversees everything from employee branding, communications and recruiting to employee performance, employee experience and diversity.

People is a relatively new leadership function as company leaders have come to realize that it’s not enough to just invest in building a great product — you also need to have an organization that can nurture your business as it grows. Though the Head of People tends to operate behind the scenes, they play an important role. Among other things, they’re responsible for coaching and directing the behavior of those within the organization.

During the pandemic, the role took on new meaning, as People teams at companies with newly remote workforces created work-from-home strategies and helped keep businesses running despite new, unprecedented challenges.

Your first People hire is critical. A new Head of People at a burgeoning startup is important for helping to build and develop the best possible team, and for building and growing infrastructure, programs and frameworks that lead teams to deliver their best work.

Any successful company requires engaged, inspired and dedicated employees who are invested in the company’s mission and vision — and that’s where the Head of People comes in. But how do you hire the right Head of People? You need to ask the right questions. Whether you’re looking for a new job at a startup’s People team or trying to hire a Head of People, we’ve collected more than a dozen potential questions to keep in mind before the interview process.

  • What is the best company you’ve ever worked for, and why?
  • What is important for retention, in your perspective?
  • What roles would you hire for now and in 9 months on the P&C team?
  • What are your values?
  • Tell me about a time you provided constructive feedback to someone who outranked you.
  • Tell me about a time where you lead without formal authority.
  • What do you want to get out of your next role?
  • What is your view on an inclusive environment? How do you achieve it?
  • Tell me about something you are proud of.
  • What are you still working through?
  • Tell me about a good and bad day at work. In each, what happened?
  • How have you worked with other leaders or gotten others on board with new initiatives in the past?
  • How do you communicate the value of your role and your team to others in the organization?
  • Tell me about a time you had to challenge your manager or have a difficult conversation.
  • Tell me how you would procure and implement a new ATS (applicant tracking system).
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