12 Must-Ask Questions for Your CEO Interviews

12 Nonprofit CEO Interviewee Questions that Reveal Hidden Challenges
You’ve experienced it. People exchange forced smiles. The person at the front desk tersely answers your questions. Everything is professional, but your gut tells you something is off.
It’s one thing to encounter an unhealthy culture at a drugstore, fast food line, or flight counter.
It’s demoralizing the first days of your new job as a nonprofit leader, especially if the interview process leads you to believe everything is great.
You can avoid unpleasant surprises by exploring critical topics during your interviews. These twelve questions will help you see what’s in the pond before you jump, determine if it’s safe to jump and begin candid interview conversations.*
Why is this important? Everyone wants to make a good impression. The reality, of course, is more complex since every organization has strengths and weaknesses.
Why are questions to detect hidden challenges especially critical during nonprofit CEO interviews? If they know the challenges exist, the interviewers fear you’ll bolt if they share them—even if they are common nonprofit issues.
For instance, in the 7 New Nonprofit CEO Success Mindsets study, CEOs told me that even in the best situations where the new CEO was thrilled with what they discovered onsite, representatives had airbrushed challenges.
Early and honest dialogs set the best foundation for the work, your partnership, and moving the organization to a better place.

🔭 Vision and Alignment

1. Where do you plan for the nonprofit to be in five years? Ten? Twenty?
What you seek: A clear vision. Does this nonprofit know where it’s going? Are people pointed in a similar direction? Do any significant vision disconnects exist?

💳 Finances

2. In the last five years, how many years did you end in the black? Why so many or few?
3. If you ended the year in the black, did it require an emergency campaign?
What you seek: Clarity on the nonprofit’s finances. I agree with Kim Klein that a healthy organization is one where “no one lies awake worrying about money more than once or twice a year.”

💵 Fundraising 

4. How much donated income do you expect this year? How did you calculate it? What revenue streams, if any, are used to “balance” the budget?”
5. Does every board member give every year? How much cash? What was the range of their gifts last year? Do members identify new supporters?
6. Does every staff member donate? Why or why not? What is the range of their gifts?
What you seek: To understand fundraising expectations. Many nonprofits use contributions to balance the budget instead of analyzing what’s possible, sustainable, and likely. If the staff or board doesn’t actively give, your inquiry gets the topic on the table. Your goal is to find or move toward thought-filled fundraising expectations backed up with board and staff gifts.

🗣 Marketing

7. What part of your mission work do people resist resourcing? How have you solved or reduced this challenge?
8. How have you grown your support, i.e., members, donors, and customers? What trends do you see?
What you seek: Most nonprofits have both attractive (playing with kittens and puppies) and undesirable needs (cleaning cages). Growing supporters is a fundamental nonprofit activity. The answers will help you discover where you’ll invest time and energy.
Closing marketing and funding challenges (you can read about the gap concept in this free chapter) require fresh thinking and planning. You also want to know if people have given up. Will your work be overcoming a been-there-done that-culture or the distinctly different challenge of leading an engaged team piloting solutions?

🎤 Leadership

9. What is the average staff tenure? On a scale of one to ten, with ten high, rate the overall staff attitude.
10. Besides board service, how do board members share their expertise?
What you seek: To gauge the staff and board engagement over time. Will you need to build teams or board a moving train already moving onward and upward?

🔥 Risks and Red Flags 

11. What three possibilities pose the most significant risk to your work and survival? What will shut you down or cause a significant scale back?
12. Does any pending litigation exist? Are there concerns with authorities that license, accredit, or fund you?
What you seek: Clarity on the challenges the nonprofit faces. The pandemic taught us that survival challenges threaten nearly every nonprofit.

Bonus Question

What would you change if you waved a magic wand?

How to Use these CEO Interviewee Questions

Learning the answers to these and similar questions will help determine if the position is a good fit for your skills and career growth.
A “bad” response does not mean you won’t take the job.
Instead, use the knowledge to better build relationships and determine if it makes sense to move forward.
From my research, the most successful new nonprofit CEOs select positions where they have polished skills that match the nonprofit’s greatest need and allow the candidate to grow. Look until you discover an opportunity for both. And once you find the position, ask for these items to jumpstart your transition.
If you’d like some guidance, it’s super easy to reach out to me by chat or email.
* Supplement these questions with your salary and benefit inquiries.

Karen Eber Davis

Karen Eber Davis Consulting guides executive directors and CEOs to generate the resources, boards, and support they need to make remarkable progress on their missions. As the award-winning thought-leader, advisor, and founding principal of Karen Eber Davis Consulting, Karen helps nonprofit leaders get answers, generate revenue, and grow their mission. Davis is known for her innovation and practicality based on her work with or visits to over 1,000 nonprofit organizations and her experience leading board and team events. She is the author of 7 Nonprofit Income Streams and Let's Raise Nonprofit Millions Together.