Six Provocative Interview Questions When Hiring Fundraisers

Hiring fundraisers can be challenging. Just ask any Executive Director or CEO. Fundraisers tend to move jobs often and most fell into fundraising without studying it as a career, making it difficult to evaluate their skill and track record. 

You’re probably experiencing this challenge for yourself right now. Whether you’re building on your successes from 2020 or restructuring after a difficult year, you are likely reexamining your fundraising model, either using an outsourcing model or hiring specific development talent to advance your mission.

Hiring strong fundraisers who fit your organization and culture is not easy but offers enormous benefits–– and it all starts with the interview. The interview is an opportunity to experience first-hand how the candidate builds relationships.

As an executive recruiter specializing in nonprofits, here are six questions I recommend for interviewing fundraisers and major gift officers.

  1. What motivates you?
    This open-ended question invites storytelling, a skill which is pivotal to fundraising success. A great answer will reveal how their mind works and create the opportunity for impactful follow-up questions about their interest in your mission.
  2. What is the most important gift you have brought into an organization? Who else was involved in bringing in the gift and what role did you play?
    Large gifts do not occur in a vacuum. There is a team that supports research, collateral, stewardship and the actual ask. Dive into their role, the strategy, the outcome, and the follow-up. Consider what the response reveals about the candidate’s strength and support needs, and whether these complement your current resources.
  3. Tell me about a donor with whom you built a relationship over many years. How did you move them up the pyramid?
    Examine the candidate’s approach to building and maintaining long-term donor relationships including strategy, networking, follow-through, and organizational skills. Listen for the origins and development of the relationship and how they engaged the donor as they moved them up the donor pyramid.
  4. How do you decide on the size of the ask you make of a donor?
    An excellent fundraiser will demonstrate research skills, strategic thinking and a comfort level with finance. There will be an established methodology around determining asks plus a willingness to adapt that methodology to changing conditions.
  5. What’s changed in your approach to cultivating donors this past year? Share one thing that worked and one that didn’t.
    The pandemic tested the adaptability of development professionals. The most effective ones shifted their approach in a variety of ways, building on the methods that worked and learning from the ones that did not. Look for someone who can turn past failure into future success.
  6. Tell me about a gift you did not take and why?
    Cancel culture has created a treacherous landscape for all companies, and non-profit organizations are no exception. Association with the wrong donor can be devastating to future fundraising efforts. Knowing how to vet donors and when to step back from them speaks to both values and judgement.


Sue Waterbury serves as a Managing Director at McDermott + Bull in the New York office, where she leads East Coast business development, with a practice focused on family offices, family foundations, and the nonprofit sector. She is a trusted advisor to senior executives and trustees on hiring leaders and developing corporate culture.

Prior to her career in search, Sue spent two decades in senior sales positions within the emerging market finance sector working as Vice President at Deutsche Bank and Goldman Sachs.

Sue serves on the Advisory Board of Citizens Committee for Children and was one of the founding board members of EMPower. She has a BA in French and Psychology from Villanova University.

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