20 Questions: Starting a Job as an Executive Director

  1. What will my legacy be with this organization?
  3. What are the strategic priorities of the organization?
  5. What are the community’s dreams for the future?
  10. What can I do to strengthen the organization’s processes?
  12. How will I strengthen the organization’s fiscal position?
  16. What are our organization’s core competencies?

20 Questions: Starting a Nonprofit

  1. What specific needs will this organization address?
  2. How has the need for this organization been discovered and documented?
  3. How will specific community needs be identified and explored?
  4. What is my motivation for starting this organization?
  5. How does this organization connect with my personal and professional goals?
  6. How does this organization fit in with the programs and services offered by other organizations?
  7. What can we learn from other organizations who are doing similar work?
  8. What resources (money, people, facilities, technology, etc.) are needed to start this organization?
  9. Who will be involved in the development of this organization?
  10. How will the community be engaged in the work of the organization?
  11. How will the work of this organization be sustained over time?
  12. How will this organization help the community served realize its dreams?
  13. What is the organization’s vision and mission?
  14. How will the strategic direction for the organization be developed?
  15. What are the specific goals of this organization?
  16. What are the legal requirements for starting an organization in my state and municipality?
  17. How will we let other people know about this organization through every stage of development?
  18. Who will benefit from this organization?
  19. How will this organization enrich the community as a whole?
  20. What best practices will guide the development of this organization?

20 Questions about Program Evaluation

  1. What is our intended impact?
  2. What are our specific goals?
  3. How will we know if we achieved each of our goals?
  4. What is our organization doing to contribute to that intended impact and those specific goals?
  5. What resources and relationships are needed to achieve our goals?
  6. What internal capacities and skills are needed to achieve our goals?
  7. What internal capacities and skills are needed to conduct the evaluation?
  8. Who will be involved in the evaluation process and what will their responsibilities be?
  9. How will we measure our progress toward our goals?
  10. How will we evaluate process, outputs, and outcomes?
  11. How will we collect data and stories for this evaluation?
  12. What data collection instruments need to be designed?
  13. How will we analyze the information that is collected?
  14. What kinds of information will the evaluation reveal?
  15. How will we use the information that is collected through our evaluation?
  16. How will the results of the evaluation be used to strengthen the program and the organization?
  17. How will we communicate the results of our evaluation?
  18. How is accountability integrated into the culture of our organization?
  19. How are the voices of program participants included in the evaluation process?
  20. How will this evaluation reveal unmet needs and how will the organization respond to these?

20 Questions to Ask When You Join a Board of Directors

  1. How does the mission of the organization align with my values?
  2. What are the responsibilities of board members?
  3. How will I meet my obligations as a board member?
  4. What information do I need to be an effective board member and how will I get and use this information?
  5. What information, ideas, resources, and relationships do I need to share to be an effective board member?
  6. How can I make a meaningful and significant contribution to the board?
  7. How can I make a meaningful and significant contribution to the organization?
  8. How will I strengthen this organization?
  9. What can I learn from serving on this board of directors?
  10. How can I share my gifts and skills with this organization?
  11. How can I promote the work of this organization in my community?
  12. What relationships should I help develop for this organization?
  13. How can I help the board to function more efficiently and effectively?
  14. How will I support the executive director and executive director?
  15. What communication means are most effective and useful for me as a board member?
  16. How will I communicate my new opportunities to the organization’s leadership?
  17. How will I communicate my concerns to the organization’s leadership?
  18. How does being a board member enhance my personal identity?
  19. What is my motivation for serving on this board of directors?
  20. How much time am I willing to contribute to this organization and how will I make the most of that time?

Let’s Play 20 Questions!

My new sometimes series, 20 Questions, will be dedicated to nonprofit capacity building. Each of these posts will share a collection of 20 reflection and discussion questions to help you and your organization strategically investigate various topics. These questions can be used comprehensively to develop a plan of action or they can be used one by one to address the particular needs of organizations. You can use the questions to prepare for meetings or present them at meetings to encourage collaborative discussion. Staff, the board of directors, volunteers, program participants, community partners, elected officials, and the community at large can all be engaged in the work of organizations by using these questions.

We will get started with 20 Questions to ask when you join a board of directors. Coming soon!

From Professional Victim to Provocateur of Possibility





I have become a provocateur of possibility.