I have a question for you. Does this scenario look familiar? It’s one I have run into with hundreds of schools over the past few years at CASE: you engage with leadership annual fund donors, make an ask of some kind, receive funds in some fashion, steward the gift for a few weeks, and then move on to another family or project. Around March, when a fundraising event is coming up, you might ask the same family for a “raise the paddle” gift toward a financial aid fund or ask them to contribute their beach house as an auction item. Weeks after that, the same family is asked to buy a foursome for the (often dreaded) golf tournament. By the end of the year, the donor has given a significant amount, but they’re somewhat worn out by the process. 

I hear about this phenomenon all the time. Donors are increasingly confused by the number of asks that are made of them, and they’re not always willing to give to both an event and the annual fund in the same year. They feel like they already gave by giving to one fund, and one ask inadvertently cannibalizes the other. Moreover, we often forget that we’re not the only organization asking things of these donors, so the sheer number of support requests coming their way can be overwhelming. 

But here’s another question: why don’t we treat annual giving more like campaign giving? In a comprehensive campaign, it would be ludicrous to make a capital ask one week and then go back to the same donor much later to ask for an endowment gift for the same project. We would never put a proposal in front of a donor that didn’t include funds for capital, annual, and endowment if we knew we wanted to ask for each type of support. So why, for wealthy, savvy donors, are we not doing something similar for our annual funds?

I’ve been working with several schools engaged in CASE@Campus programs on the notion of comprehensive asks for leadership level annual fund gifts. Each school to which I’ve recommended this method has significantly increased its fundraising in the first year. That might look like the following: 
 

1. Identify how much each leadership donor gave the prior fiscal year.
    
2. Put a formal ask on paper for each leadership donor OR each leadership prospect, in the case of new families or recently reengaged alumni (or use an email, should geography or preference make paper problematic). After some introductory language of gratitude and the case for support, break the ask down as follows: 
   1. $_____________ in annual giving. 
   2. $_____________ in gala support (including the value of goods, services, or properties donated).
   3. $_____________ in other funds for ___________ purpose.

   4. Total charitable giving in XXXX fiscal year.

      Don’t forget to upgrade this gift from the prior year with some small justification based on inflation, the cost of programming, the donor’s own generosity, or something similar. You should also remember that just because you’re putting different types of support in one letter, doesn’t mean you have to “count” it all as annual fund. You get to allocate the funding in the appropriate buckets, so long as you’re transparent with the donor about what they’re supporting with each amount. 

3. Identify someone who can follow up specifically with the family. Depending on the amount and the donor’s profile, choose the most appropriate person: a volunteer, the annual fund director, the Chief Advancement Officer, the Head of School, or a trustee. Philanthropy is a team sport, so use resources to your advantage. 
    
4. Before sending the ask, set a date by which follow-up should happen; ensure the follow-up is a phone call, video call, or in person meeting. 
    
5. Track the dates of the ask and the follow-up, along with anything else you learn in the process.

This doesn’t have to be an arduous process. If your database can’t do this, then use a spreadsheet with separate columns for each type of support and a mail merged letter to help you. 

If you follow these steps, you will enable your families to clearly see what you’re asking for, why you’re asking for it, and what their overall commitment to the school will be for the coming year. They can plan accordingly and will feel less burdened or nickel-and-dimed. They want a transparent, clear set of expectations just like anyone else, so give it to them early in the year and secure their full pledge ahead of major events. Not only will this help them, but it will help you. You will reduce overhead cost and staff time by asking once instead of three times. With careful planning, everyone wins. 

“But, Ann,” you might say, “what if they say no?” Well, be brave. We get a lot of “no” answers in fundraising, but each negative response will lead you closer to the donor’s “yes.” Having these conversations will take the guesswork out of your annual giving program. Find out why the donor doesn’t want to give, or which aspect of the ask doesn’t sit well with them. You can then tailor the ask or create a new ask based on the conversation. They will feel heard, and you will have more information and firm numbers to inform your annual giving success down the line. 

Fundraising is often a game of Chutes and Ladders. Sometimes you land on a chute and it feels like a setback, but it’s all part of the process of moving toward the goal. Unlike in the classic children’s board game, you have more than just the roll of the die to rely on: learn from your donors and listen to what they tell you. Your program will eventually flourish as a result.