Before You Say Yes: Questions Every Executive Director Should Ask

Dear Prospective Executive Director:

Congratulations on having made it to the final round of interviews for a job to be executive director or president/CEO of a nonprofit. I’ve been in your shoes, and I’ve also been in the role of the people interviewing you–whether they are a board chair or a member of a professional search team.

Being considered for a leadership role makes us rightly feel flattered, excited, and dreaming of the possibilities that this new role will bring to our professional and personal lives. This adrenaline can make us lose sight of the fact that once we get the job, we’re going to have to do it, and to stay in it (and stay happy), we will need to be successful in reaching the organization’s goals.

These are some of the questions I wish I had known to ask or that I wish someone had asked of me when I was in the hiring seat. The answers wouldn’t have necessarily changed my decision to take or not take a role or to hire or not hire a candidate, but they would have helped broaden my understanding prior to taking the next step.

Are you energized by the mission?

• Do you follow trends, policies, or innovations in this space because it genuinely interests you?

• Are you enthusiastic about dedicating your professional energy, creativity, and leadership to advance this mission?

• Does the cause align with your values?

(When I worked at the Chicago Botanic Garden, a wonderful new development director joined the team. She was competent, vibrant, but there was just one problem–flowers and nature just weren’t her thing! It’s hard to sell something that doesn’t excite you. She left a short time after she started.)

Do you know what the board wants from its next leader and the future of the organization?

• Have you seen current or past strategic plans?

• If there hasn’t been a strategic plan, why not?

• Do you know whether the board will support you in launching a strategic planning process–most likely in your second year (so you get a year to understand the organization from the inside)?  

• How engaged and effective is the board?

• Have you examined key performance indicators and program outcomes?

• Do you understand the governance structure and the board’s expectations for the chief executive?

• Have you met with key staff, board leadership, and community stakeholders to understand the challenges and opportunities?

Assess organizational health.

• Have you evaluated the financial strength and revenue diversity, reviewing audited financials, board meeting minutes, and Forms 990?

• Have you asked about pending legal, reputational, or staffing challenges?

• Does the organization offer appropriate insurance coverage, retirement plans, and sound HR policies for all employees, full, part-time, contractor and freelance?

• Has there been any unionization effort in this organization or others in your sector?

(If the organization is unhealthy or you can see some storms on the horizon, that’s okay ... .you may want to take on its challenges anyway, but it’s good to know in advance!)

Can you lead from strength?

• What unique leadership, fundraising, strategic, or operational strengths do you bring?

• How will your experience help the organization achieve its goals more effectively?

• Where would you need support or collaboration to thrive?

• If your background is in the for-profit world, are you ready in your skills and mind-set to move into the social sector? The goals are different, the accounting practices are different, and “applying a for-profit mindset” despite how silver-bullet that sounds, often backfires (and makes a new leader look condescending and naive). 

Is there a cultural fit?

• Do you feel you can build trust with the board chair and board members?

• Will you enjoy working with this team daily, even during challenges?

• Does the organization’s culture align with your leadership style?

Are you ready to be the face of the organization?

• Are you ready to be the voice and face of this organization?

• Does this organization represent something you’d be proud to stand for in all aspects of your professional and personal life?

What will you gain?

• What do you hope to learn or build as a leader through this experience?

• Is this the right next step in your career trajectory?

• Will this role bring a sense of fulfillment and meaning?

Look beyond the resume fit.

• Can you see yourself spending years helping this organization evolve and grow?

• Are you excited by the day-to-day work as much as the big-picture goals?

• Can you help build something here—and enjoy the journey?

Final thoughts:

Becoming a nonprofit Executive Director is one of the most rewarding and demanding roles in the sector. You’ll be called upon to inspire, to navigate complexity, to build culture, and to deliver results. The best leaders step into the role with clear-eyed purpose, deep enthusiasm, and an honest understanding of what they’re getting into. Ask the right questions now—so that you can lead with confidence later.

In support,

Sophia