8 Essential Interview Questions for Hiring Executive Directors and Development Directors

In the search for exceptional leadership talent, we've gathered insights from top executives and directors on the pivotal interview questions they pose to candidates for roles like Executive Director or Director of Development. From inquiring about detailed fundraising success stories to assessing moral courage and conviction, explore the eight critical questions these seasoned professionals rely on to identify the ideal match for their organizations.

• Detail Fundraising Success Stories
• Discover Vulnerability and Development Needs
• Explore Resource Allocation Strategies
• Gauge Organizational Knowledge and Risks
• Evaluate Connection to Donor Humanity
• Understand Failure Management
• Discuss Vision and 90-Day Plan
• Assess Moral Courage and Conviction

Detail Fundraising Success Stories

When recruiting for pivotal positions such as Executive Director or Director of Development, identifying a singular, definitive interview question can be challenging without follow-up inquiries. However, a good starting point involves asking candidates to detail their most substantial, successful fundraising efforts, specifically their largest solicitations from an individual, a foundation, and a corporation. 

Candidates should explain why these efforts were successful and the challenges they surmounted to achieve these outcomes. It's vital for applicants to recount their experiences in a STAR (Situation, Task, Action, Result) format, providing a comprehensive narrative of their achievements and problem-solving skills.

Lynne Williams, Resumes & LinkedIn - Executive Director, Great Careers Groups

Discover Vulnerability and Development Needs

What are the one or two aspects of this job that terrify you? I like this question for a couple of reasons. First, it tests how vulnerable the leader is willing to be. I find that leaders and performers who are willing to be vulnerable are more likely to succeed in a role than someone who puts on a facade. If someone answers, “Nothing about this role scares me,” I will most likely dig in a little bit more to understand their personality and approach to failure. These are critical aspects of success for many organizations. 

Second, it helps me understand what type of development plan we should develop to ensure success. The answer allows me to craft a journey map of development and have it ready for the employee within the first week or two of hire. This process also says a lot about an organization that is willing to take the time to prepare them for success.

Trent Cotton, Senior Director of Talent, Hatchworks

Explore Resource Allocation Strategies

How do you prioritize competing demands and allocate resources to ensure that the most critical objectives are met? This question explores both a candidate's approach to resource management and their commitment to the organization's strategic objectives. 'Show me the money!'

Michelle Forstrom, HR Manager, BYU Library

Gauge Organizational Knowledge and Risks

What do you see as the biggest short-term opportunities for this organization, and what challenges and risks do you see in achieving them?

This question allows the interview panel to determine how familiar the candidate truly is with the organization as it is and its trajectory, while assessing how comfortable they are in asking for help. In answering this question, the candidate has an opportunity to reinforce their fit or convince the panel they can take the organization in a new direction. 

Furthermore, while walking through risks and concerns the candidate may face in the first year of service, a good leader will acknowledge the ways in which they may need board or staff support, which can demonstrate their leadership style and whether it will support the kind of team dynamic that is compatible with the organization.

Lonny Stern, Executive Director, Movability

Evaluate Connection to Donor Humanity

I believe our leaders and development professionals must never lose sight of the humanity of their work. We are not in the data business, though we use data. I like to ask candidates to give me examples of 1) when they were most moved by a donor's actions/decisions and 2) when a donor was moved by the opportunity to make a gift that the candidate was responsible for. 

Whether they have an answer, and the depth with which they answer, gives me strong clues about how connected they are to the people in the process. I also get a sense of their storytelling skills, which is critical in both roles.

Dion McInnis, Fundraising consultant, Dion McInnis Initiatives, LLC

Understand Failure Management

Being in a leadership role means fostering a lot of talent, managing a lot of decision-making, and knowing how to discern between business tactics that will lead to wins or losses. It's one thing to be a constant success driver, which proves their competence and vast experience; it's another to be able to navigate failures, big or small, and still keep the team morale up and envision how to improve things. 

People love to brag about their achievements, which speaks a lot about their credibility and skill, but people who know how to acknowledge their misses and take responsibility for not just their own losses but also their team's take a lot of guts and courage that anyone in a key role should be able to take on.

Jamie Frew, CEO, Carepatron

Discuss Vision and 90-Day Plan

I like to understand the vision of a candidate at this level, so I ask: "If you're selected for the position, what would you do in the first 30-60-90 days? Walk us through what that plan would look like."

Amanda Haddaway, Managing Director, HR Answerbox

Assess Moral Courage and Conviction

For pivotal leadership roles, past proficiencies matter less to me than unteachable attributes—innate curiosity, grit, and integrity. 

So I always ask, “Can you describe a time you took a principled stand, made an unpopular decision, or overcame opposition to do what you felt was right—even at personal risk or cost?” I listen closely not just for the story itself, but for raw self-honesty. Earlier in my career, dazzled by a candidate's charisma and accomplishments, I overlooked red flags in their response. The hire seemed a coup initially, but that person ultimately put self-interest above our mission. 

Now, through this question, I assess moral courage—because wells of conviction and resilience cannot be trained. I seek leaders driven by an ethical compass over external validation. Those who've persevered through scarcity and criticism with values intact know how to unite teams in driving towards greatness, bending reality to a lofty vision. Details of triumphs may differ, but such spirits shine through.

Lou Reverchuk, Co-founder and CEO, EchoGlobal

Keep these interview questions in mind as you're navigating the hiring landscape for Executive Director, Director of Development, and other crucial fundraising positions. 

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We extend gratitude to the experts who provided their insights for this post created in partnership with Featured.