Hiring an executive director is one of the most critical—and challenging—decisions a nonprofit can face. The role demands a rare blend of leadership, management, fundraising, financial savvy, and strategic vision. Add to that the need for exceptional communication skills and a deep, personal connection to the mission—and the ideal candidate begins to feel mythical.
The executive director must also navigate a complex web of relationships, balancing the needs of board members, staff, donors, and the community. It’s a role that calls for both heart and diplomacy.
This guide is designed to help boards and leadership teams make thoughtful, informed decisions that strengthen their organizations and prepare them for lasting impact.
“Tell me about a time when you utilized your knowledge of fundraising to successfully meet or exceed a fundraising goal.”
Red Flag: Has not met fundraising goals; has not been able to generate resources that needed to be raised/generated
“Please provide an example of how you used a software application to analyze data and what action you were able to take based on your findings.”
Red Flag: Seldom use software and data analysis tools
“Tell me about a time when you successfully led a team through a major crisis.”
“Tell me about a time when you led, initiated, and implemented a strategic transformation within your organization that resulted in significant positive change. What process did you follow?”
Red Flag: Followers are involved only grudgingly; process is cumbersome or minimal improvements result
“Can you walk me through a time when your nonprofit faced limited funding or financial uncertainty and what strategic decisions you made to optimize resources?”
Red Flag: Placed too much emphasis on one low-impact approach.
“Can you tell me about a time when you identified a significant external trend or global shift—such as technological change, regulatory developments, or societal expectations—and advocated for a strategic change within your organization as a result?”
“Tell me about a time when you have led a successful advocacy campaign. What was your approach to communicating with stakeholders?”
Red Flag: May have led an advocacy campaign or activity but not a successful one
“Could you tell me how your organization benefited from a helpful and productive relationship you developed with someone from another culture?”
Red Flag: Doesn't adequately explain how the organization was served strategically by this relationship.
“Tell me about a specific time when you had to initiate a difficult conversation with a board member or key stakeholder to address a mistake or misstep that had occurred. What was the situation, how did you approach the conversation, and what was the outcome?”
Red Flag: Minimized the issue or avoided taking ownership by shifting blame to others.
“Tell me about a time when you had to implement a necessary workplace policy change but met with resistance from staff.”
Red Flag: Framing staff pushback as a problem rather than part of the process.
“Can you walk me through a time when you led a mentoring or coaching initiative that helped one or more team members grow as leaders?”
Red Flags: No specific example given, no real outcome or impact, vague or superficial actions, no understanding of leadership growth
FirstWho’s Social Impact Hiring Institute (SIHI) provides resources to nonprofits and public benefit companies to promote evidence-based methods for attracting and selecting leaders who create meaningful social impact.