CBS has been 3rd in the morning TV news ratings for over 30 years. Charlie Rose will be leading their charge to change this from 7am-8am, bringing a serious tone to an otherwise increasingly witty, wacky and pop-culture-filled hour led by NBC’s ‘Today’ and ABC’s ‘Good Morning America’. Rose is perhaps the single best interviewer I have ever seen. His questions get to the heart of issues and people, facilitating a beautiful dialogue, filled with insightful verbal challenges, full disclosure and shared understanding. Here are 29 questions that I think he’d ask of current and potential supporters – and of development officers – that will take you further in your philanthropic relationships.

Ask supporters…

1. What’s the largest impact you’ve had on the world?
2. The world needs band aids AND solutions to social problems. Which do you prefer to invest in and why?
3. How do you plan on teaching your children about philanthropy?
4. Are you hoping they (your kids) have the same community values or different ones?
5. What’s been your best giving experience?
6. What’s been your worst?
7. What person has had the most influence on you and your life?
8. How do you and your spouse/family make your philanthropic decisions?
9. Do you prefer to give a little to several organizations or more to a few?
10. What are your top 3 philanthropic interests and why?
11. How long do you usually stick with an organization or issue?
12. If you could volunteer full time – what would you do?
13. How do you define success?
14. What lead to you being successful?
15. How can we give others those same opportunities?

As a current/potential supporter, ask fundraisers or nonprofit leaders…

1. What motivates your employees and staff?
2. What does the organization look like in 5 years? 10 years?
3. What are your current costs per client?
4. What sort of impact are you getting for that?
5. Summarize your current strategic plan for me.
6. Who’s doing similar-type work?
7. How are you working with, or at least learning from, them?
8. What’s the best way to for me to introduce my network to you?
9. What connections/introductions can I make for you?
10. I’m making an unrestricted gift. Where/how will you use it and why?
11. What sort of professional training does your staff have?
12. What kind of turnover are you seeing and why?
13. How does the organization define success – and are you reaching it?
14. Can philanthropy solve this problem? If so, how much money is needed. If not, what else needs to happen?

So grab coffee or a meal with your favorite supporter or nonprofit staff and have a deeper conversation.  What’s missing? What questions would you ask?