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A pain in the ask

Have you ever found yourself in the position of asking someone for 50 million dollars? Five million? Five thousand? However big a “big” ask typically is for you, chances are that you don’t relish the task. In fact, an entirely unscientific study suggests that most people would rather have a root canal performed by a first-year dental student than ask someone for a significant amount of money.

For fundraising professionals, making big asks is an important and necessary part of their jobs. But executive directors and board members – often without formal fundraising experience or training – also find themselves with the unwelcome responsibility of asking an influential prospect for a large sum of money.

But there’s a distinct difference between making a big ask and making a BIG ask. A big ask is asking someone with a boatload of money for a boatload of money simply because they have a boat and you need the money. If it feels icky it’s because it is.

By contrast, a BIG ask is one that is Bold, Interdependent, and Generative. A BIG ask is not defined by the number of zeros, but rather by the relative impact the gift has on the organization and its community, as well as on the donor. A BIG ask recognizes that we are, cliché as it sounds, all in this together. Whatever, exactly, “this” may be.


If your mission is a worthy one, be bold and confident in your ask. It’s the only way to push beyond the status quo. But remember, there is a difference between boldness and carelessness. Your position to be bold is directly tied to your due diligence and attentiveness; if you’ve done the appropriate research on your donor, you can afford to be bold because you’ll know not only what they can afford but what motivates them to give. Being bold tells a donor that you’ve done your research, you’re confident in your organization’s worthiness, and you value their commitment.

To be clear, being bold is never an excuse for being insensitive or arrogant. You should always be professional, courteous, and humble when interacting with prospects and donors (or anybody, for that matter). It might sound counterintuitive to be simultaneously bold and humble, but the late and honorable Ruth Bader Ginsburg has proven it not only possible, but deeply powerful.


If this pandemic has taught us anything, it’s that we are all connected. That, and how to make sourdough bread. But while independence is often celebrated as the pinnacle of success, interdependence is in fact the mark of the most mature, advanced organization. As organizational guru Stephen Covey observes, interdependent organizations “have access to the vast resources and potential of [others]. Interdependence is a choice only independent people can make. Dependent people cannot choose to become interdependent. They don’t have the character to do it…”

As you strategize your ask, position your organization as an independent and autonomous one, rather than one dependent upon your donor. When you openly share that combining your efforts with that of a donor will achieve greater success than you could achieve on your own, you project humility – a virtuous characteristic becoming of any cause. (And especially powerful when paired with being bold, but we’ve already covered that.)

Your organization can’t achieve its worthy mission alone. Wealthy individuals can’t save the world alone. But, together, you can be truly generative, which is what puts the “G” in BIG.


To be generative means creating new ideas and opportunities for others while simultaneously creating value for yourself. It’s about activity that yields more than it consumes. The challenges of our day are too complex, too intertwined – interdependence is a double-edged sword, after all – for any one entity to tackle on its own.

Connect the dots of your collective potential for a donor. Start with the end and paint a picture of what is possible. It’s ok if it’s ambitious and lofty. Bold. In fact, it’s better if it is.

When you’re faced with making a big ask, be upfront with your donor. Acknowledge that it’s a BIG ask and explain how that is different from a big ask. Tell them that they are worthy of such a BIG ask. Break BIG down for them: an opportunity to be bold. To play a meaningful role in an interconnected system. To generate something that couldn’t exist but for their contribution.

Approaching a big ask as a BIG ask can profoundly change a person’s willingness to make one. A fundraiser’s willingness to make an ask and a donor’s willingness to make a gift.

Together, that’s BIG.

This article originally appeared on Collegium’s website.