Reinventing hiring interview questions

A client asked me to help them develop a set of candidate interview questions for their Director of Major/Planned Gifts position. They wanted unconventional questions (my specialty!), ones that would engage candidates in a deeper, richer conversation. My assumptions/frame when developing the question set for this leadership position:

  • We live in a time where EVERYTHING demands reinvention. Why not the way we approach basic hiring interview questions?
  • The candidate’s resume conveys experience and strengths. I don’t need to ask them to reshare that information verbally.
  • Can they improvise? Have they dealt effectively with the unexpected?
  • What life lessons have they learned that have influenced their work?
  • Have they thought about their ongoing development, seeing us as a willing and welcoming partner in that?
  • I want to know if this is somebody I want to work with.
  • How can our questions convey that we’re the kind of organization they’ll want to work with/for?

I got to sit in on the interviews. The questions worked BEAUTIFULLY in the client context. Even the candidates thanked us for the richness of the questions, suggesting that it gave them new insight into the cultural pillars of the organization.
How might you adapt these questions for job candidates you’ll be interviewing soon?
Here's what I came up with.
Let me know if/how you improve/adapt them. Maybe we can build a new question bank for future reference.
Interview Questions

  1. If every major action we take is evidence of a story unfolding, what story about you is unfolding by the act of pursuing this leadership position?
  2. We’ve recently been blessed with a $25M challenge gift that requires us to raise an additional $100 million in the next 15 months. Through this role, what contributions can you make to help us meet the challenge? What strengths of yours will you rely on most?
  3. Let’s stay with that line of inquiry a moment longer. As you saw in the position description, the role comprises 3 essentials: masterful fundraiser, team developer, and advancement leader. Among these three, where will you naturally shine and how will you navigate and balance inevitable competing priorities?
  4. What does it mean to you to create the conditions for team success?
  5. What is the most powerful and unexpected question you’ve ever been asked by a benefactor…and how did you handle it?
  6. In the last 10 years of your career, what’s been your biggest life learning and how did it amplify your strengths?
  7. In the last 10 years, what’s the biggest personal fear you’ve had to address…and how did you learn to navigate it?
  8. Now it’s time for everyone’s favorite activity….ROLE PLAYING!! Have a go at asking us to offer you this position, drawing upon your experience of asking major donors for big gift investments.
  9. We are deeply committed to helping you grow and develop as a professional. In the next few years, what would position you for your next successful chapter? What could we help nourish and strengthen in you to make this work deeply satisfying and your next chapter all the more possible for you?