Last night I made calls for the YWCA of Lancaster's Annual Campaign phone-a-thon. I am on the board, and as such, volunteer there in many capacities, but I have to admit, I truly enjoy the opportunity to "smile and dial" in support of a great organization.
The YWCA actually had a great angle on the phone-a-thon that made it very successful and that you may want to consider. They had an anonymous donor who matched every increase from 2008 Annual Gifts, and fully matched the gift of any lapsed donor who returned in 2009. So a donor who gave $50 in 2008 and $75 in 2009 would have the $25 increase matched dollar for dollar. A donor who gave $100 in 2007 and returned to the YWCA in 2009 would have their entire gift matched.
As a caller, this gave me a great way to maximize every call. Instead of feeling awkward asking for an increased donation in a tough economy, I could say "Last year you generously gave $100. This year we have a benefactor who will match any increase in that amount this year. Is it possible for you to give a little more?" Nearly every caller who was planning on giving again increased their gift - even if only by $5 - although some by much more. It was easy for me to ask, and very satisfying to know my time calling on behalf of the YWCA produced so much more than it might have otherwise.
Of course, there were a couple of past donors I called who could not give in 2009 due to economy-related circumstances. They all expressed gratitude for my call, however, and remain extremely supportive of the YWCA's mission of empowering women and girls and eliminating racism. They were not awkward conversations in the least.
If you have a strong supporter who is looking to help your organization in a creative way, do consider asking them to provide matching gifts for increased gifts as the YWCA of Lancaster did. I bet you will find it to work very well!

This is an excellent idea!!
I'm the receptionist for our agency, and am THE person responsible for GW. I took these ideas immediately to our Development Director and she loved them!!
Kudos to you all for thinking of it!!
Erycha Butler
said on Apr 8 at 11:55AM