The Art of the Ask is simply understanding your audience and responding to their needs. This means knowing for certain: 

• What you’re asking for 
• Who you’re asking & why they care 
• How to deliver it
• Who should deliver it 

This is a straightforward task for a chamber of commerce or economic development organization (EDO) engaged in traditional fundraising, where asking is expected—and responses are rote. 

But this article focuses on asks of greater magnitude–those that have weightier objectives, higher commitments, and a much different audience. Here, you’re engaging with investor-level funders that have little bandwidth, and a lot at stake.

For these investors, it isn’t enough that you ask, but how and why. Before making an ask, consider the following five steps to ensure your ask yields high engagement and positive responses:

1) Determine Your Type of Ask

Every ask carries a degree of transformational potential and relevance to investor priorities. The higher the transformational potential and relevance, the better the ask. In light of your objectives, determine what type of ask you will make and why.

Investors will hear your ask and categorize it into one of four types:

• Catalyst: bold, large projects or initiatives that warrant substantial, multi-year funding 
• Vision: innovative, speculative, potentially risky ideas that pay dividends if successful
• Business As Usual: transactional appeals that “keep the lights on” and maintain regular programming
• Civic Overhead: generic offerings, few direct benefits

The graphic below illustrates specific asks and charts them on a matrix of transformational potential and relevance to investor priorities. 

2) Define Your Audience

Determine your audience and their needs—who are you targeting and what do they want? Members, investors, investor-level prospects, local employers, and government officials have vastly different priorities—not every ask will apply. In fact, few will apply:

• A bank CEO may invest in a multi-year business attraction program (Catalyst), but has no bandwidth for managing his bank’s chamber membership (Business As Usual).
• A small business owner thrives off relationships and may buy a table at the annual gala (Business As Usual), but is less likely to have capacity for a jobs initiative (Catalyst).

With these examples, you can see that what is important to your organization is not relevant to all; thus, fundraising is not a numbers game, but a value-offered game. To eliminate irrelevant asks is to increase the relevance and value of those you do make.

3) Match Asking Tactics to Asking Type

Each ask type in our matrix holds relevance for its specific audience, but each ask must be accompanied by a distinct tactic and context to yield optimal outcomes:

• Catalyst: private, intentional meetings among a select, elite group of decision-makers
• Vision: exploratory groups or one-on-one conversations; curated pitch events or workshops
• Business AS Usual: brief personal or automated emails soliciting renewals or rote, transactional contributions
• Civic Overhead: offers via mass email, cold calls

4) Provide Proof, Not Promises 

Support your asks, especially Vision and Catalyst types, with data. What will happen as a result of the investor’s commitment? Nobody knows the future, but you can demonstrate credibility and preparedness by showing how your initiative reflects local data, community priorities, and the outcomes sought. 

Additionally, case studies, economic impact analyses, and stakeholder input will illustrate real-world effects, and contingency plans for any associated risks will demonstrate your intention to steward their funding with care. 

In doing these things, you will be presenting evidence instead of assurances which will increase the relevance and credibility of your ask. 

5) Match the Messenger to the Message 

The asker signals importance before a single word is delivered; significant financial asks are best delivered personally by top leadership. Strategic vision or major directional shifts should come from your CEO, board chair, or another credible and engaged member of the board. Program updates belong with program leads or subject-matter experts, while events and general updates are best suited for communications staff. 

A messenger with high status naturally elevates the message, and investor confidence rises. 

Implementing the Art of the Ask

The key to the Art of the Ask is understanding what investors want. This is what relevance means and it’s why NCDS developed the Roadmap to Relevance and Revenue: to establish a deep understanding of what your community’s most prominent investors need out of your organization’s leadership. 

In eight weeks or less, NCDS’ Roadmap will work alongside your organization to develop a firm, point-by-point foundation of relevance based on stakeholder needs. This relevance provides you stronger asking rights and sets the stage for transformative levels of funding potential.

If your organization is preparing to embark on a capital campaign or a new strategic plan, consider NCDS’ Roadmap to strengthen alignment, clarity, and credibility before the time comes to make major asks. Contact us for a free consultation, or download the Roadmap brochure here. 

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