Dear Kim:

I’ve been the Executive Director of a small nonprofit for almost nine months. We’re working hard to rebuild our donor campaign, including building up major donors. One of my staff members has been a major donor in the past; in fact, one year she donated her part-time salary back to the agency. I am not at all sure of the best way to approach her about donating again to the agency. As her supervisor, it feels very uncomfortable to me to ask her directly. FYI, she started with us as a volunteer and has moved up to a director of one of our programs. Any suggestions?

-Searching for Boundaries


Dear Searching:

The fact you see this as a dilemma speaks well for your sensitivity to your staff and to your role in relation to them. However, although you may feel uncomfortable broaching the subject with this person, she will feel at least a little strange and possibly miffed and unappreciated if someone doesn’t thank her for what she has done and ask what she wants to do this year. Her feelings trump yours. Before asking her find out what her situation is (or was) that enables her to be so generous. Does her partner earn enough money for both of them? Does she have some inheritance? Did she win the lottery the year she gave, and now is back to needing the salary? You will feel more confident if you know that she is still in a financial position to consider a large gift. You can consider whether someone else could ask her. The previous executive director is a candidate if he or she left on good terms and was friendly with this person. The development director, who is more her peer on the organizational chart, is another possibility. Personally, I would favor you doing it because I think it will be straightforward and will be most logical to her. It will set a good tone of honesty from the beginning of your tenure.

You should do one more thing before anyone asks her, and that is make your own gift to the organization. Then thank her for the example she set for everyone and tell her you are glad to be working with someone as committed as she clearly is. Ask how she first became a volunteer. You want to know all your staff better, and this is how you will get to know her better. She is clearly a valued member of your organization, and you will want to reinforce that. Then ask her how she is thinking about her giving to the organization now. “I’d love for you to continue giving if you can and want to, at whatever level seems right.” She may not give, or she may not give as much as she has in the past, but she will be pleased that you asked her and that you acknowledged how important her gift, as well as her talents, have been and remain to the organization. And she may well surprise you with another very generous donation.

Good luck!

Kim Klein