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What to Ask Before Saying "Yes" to that Nonprofit CEO Position

Ask the right questions about 6 areas of an organization before taking on a new nonprofit executive director role.A certain level of imagination is appropriate when considering any career change. After all visualizing your future state, in part, is what allows you to pursue positions or priorities most aligned with your passions and interests.

However, at a certain point when pursuing a new position as the CEO or executive director of a nonprofit organization, youll need to snap back to reality to ask the board your interview questions.

About a third of my clients over the course of my practice have been individuals newly appointed to the nonprofit CEO or executive director position. Many have been blindsided by significant challenges that made the first year (or sometimes first several years!) of their tenures about correcting failure work and righting the ship rather than about bringing forth their visions.

Perhaps these leaders didnt ask the right questions. Or perhaps the boards were not forthcoming or were blind themselves to the true conditions of the organizations. In either case, the new CEO arrived to find a hot mess they were now obliged to clean up. Working aside these leaders, I can tell you that the stress these individuals faced was enormous.

To help you avoid a similar plight, drill down in these 6 areas with the board during your interview process.


Explore the quality of the relationships the organization has with external stakeholders. Are these relationships collaborative, contentious, or non-existent? If the organization works hand-in-hand with other entities — for example, your municipality — how are these relationships? What level of autonomy or interdependence do the organizations have?

Fraught relationships will require a great deal of time and effort to repair.


An organization’s financial state should be an obvious point to discuss during an interview. You’d be surprised what gets concealed. Ask what the revenue sources are and whether they are reliable and profitable. One client found out the previous leader had gone on a spending spree, burning bridges with funders. and no alternate sources of revenue. To make matters worse, this individual held important individual donor relationships that went out the door with him. The operations and programs were outdated and unsustainable, and the board either didn’t know or failed to mention this sorry state. 

Do not turn a blind eye here, lest you’ll be cleaning up somebody else’s mess.


Pay attention to the culture of the organization, both at the staff and board levels. Is this a supportive environment? Or siloed off? Is the board supportive, passive, or domineering (more on the board below)? Are people talking about innovating and improving? Or are they dug in, too wed to the way things have always been done, and clinging to fiefdoms?

Much of our culture — including the nonprofit sector — is experiencing enormous transformation. Organizations that reject the evolution required to adapt are on the road to entropy. The amount of energy you’ll need to revive it and reconfigure the team to do it will be considerable. Many a client has shed blood, sweat, and tear doing so.

Board support

I’ve noticed three patterns when it comes to the board-CEO or executive director relationship. 

  1. In the first pattern, the relationship is quite healthy, with natural give and take, collaboration, sharing of leadership, and support. 
  2. In the second, the executive flies under the board’s radar, doing his or her own thing and leaving the board in the dark. 
  3. The third pattern is when the board that constantly undermines the executive’s decision making and authority, emasculating the role. (I suspect this dysfunctional relationship is actually a two-way street.)


One of my clients found his role continually made impotent by an enormous board, which elected leadership annually. No sooner had the executive and board chair begun to move in alignment when it was time for a new chair. The organization, it seemed, was all about serving the board and all its egos. Progress on mission was constantly one step forward and one backwards. Needless to say, my client moved on.

During your interviews, pay attention to your interactions with board members and the dynamic of the group. Ask questions of the board and interim CEO about by-laws, board engagement, and support of the organization. And beware the founder who serves on the board, reluctant to give up his or her baby, a dynamic that will become your albatross.


You know you’re entering a great organization when the previous leader took care to leave the organization in good shape, cleaning up any messes and ensured the organization is on solid footing. He or she may not know how to take the organization to the next level — that’s where you come in — but the organization is not about to fall off the cliff.

Ask about the vision of the organization and where the board leadership intends for the organization to go next. Ask the staff the same question. Are these answers aligned? Now ask yourself whether you are in alignment with this vision and whether you have more to add and contribute to it.

Your appetite for change

Factoring in all this data and information, ask yourself what your capacity and appetite to change an organization is. Some leaders thrive on rebuilding, while others do not relish having to be turn-around specialists. Know your limits and preferences. And don’t go it alone. Having external resources, who have helped new leaders embed their visions and galvanize support and capacity for them, provides you with a necessary ally through the process.

No matter where your new nonprofit CEO position will be, you will certainly expend energy to bring forth your own vision for the organization. These tips will help you do it with an organization that is ready to evolve and enhance its impact, not one that needs to be saved.

What have you discovered? What other area of the organization needs to be explored? I welcome your comments.



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