Spoiler alert: The Ask is not the most important part of securing a donation. That’s right, while asking for money is definitely a crucial part of the fundraising process, there are a bunch of other steps we can take to make that part a breeze!

And listen, we’re the first ones to acknowledge that no one “likes” talking about money because, well, most of us have been made to believe that it’s impolite, or for some it’s just downright awkward! But, fear not! We’re here to help you get comfortable with the uncomfortable, because it WILL make a difference for your mission.

It’s important to note that this particular post focuses on potential donors with high capacity – we’re talking 5, 6, 7 figures. This probably won’t be the exact strategy you use with your mid and lower level donors, but you can definitely apply elements of these recommendations to all your donor communications.

Without further ado, here are our 5 tough truths to help you become more confident in making The Ask:

1. It’s not about you.

While you’ve most likely got a personal connection to your work (we hope), when you approach a potential donor, you’re not asking them to fund you personally, you’re asking for money to support the life-changing work of your organization.

Seems like an obvious statement, we know, but it’s an important one. While it’s crucial that we build relationships with potential donors, we don’t want to blur the lines so much that it feels like we’re teens asking our parents to pay for homecoming. 

Your potential donors have money that they’d like to use to support a great cause, and you’ve got a great cause to support! As a fundraiser, you’re there to connect the dots and be a great steward along the way. Should you share about yourself, your values, and your journey – YES. But while the connection is yours to make, the investment is for the community of care you represent. Reminding yourself of this important fact will go a long way in helping make The Ask less awkward, and will help you recover quickly if the answer is “no” (we’ll get to that later).

2. The magic isn’t in The Ask.

Let us let you in on a secret, there’s no amount of finessing you can do to make asking for a major donation less awkward if you haven’t done the groundwork to build a beautiful connection between your organization and the prospective donor. The magic isn’t in The Ask, it’s in the preparation, the prospect research, the discovery conversations, the presentation of areas of need, the vision boarding, and the impact reporting.

Like we mentioned in our Ins and Outs for 2024 (yes, it’s the list that keeps on giving) your donor should NOT only be hearing from you when you ask for money. If you’re only reaching out when it’s time for another gift, you’re asking (pun intended) for them to take their money elsewhere.

Don’t focus your energy on trying to find the perfect way to ask for a donation. If you’ve done the work of getting to know your donors, The Ask will be a natural progression, and heck, your donor might even initiate that conversation.

3. The signs are already there.

The best fundraisers are the people that get really good at picking up on the hints from potential donors. Now, you don’t have to be, like, Criminal Minds’ BAU level of perceptive, but you should learn to recognize common behaviors that let you know a donor is ready to commit, or not.

If every time you try to schedule a meeting with a donor they end up canceling for an unforeseen appointment or something they “just have to take care of”, it might be an indication that they’re not ready to invest. In this case we’d recommend being up front with them and saying something like “It’s seeming like now is not a great time for you as we haven’t been able to meet. We are so grateful for your interest in supporting our work and would be happy to schedule another meeting when you feel ready to discuss an investment in our programs.”

On the other hand, if your potential donor starts asking questions like “When we move forward with this expansion project, what will the impact look like?” Chances are pretty good you’ve got this in the bag! (Note: The use of “we” on the part of your prospective donor is a big green flag to go make that ask!)

4. The faster you get comfortable with “no”, the more money you’ll raise.

Listen, you’re gonna hear the word “no”, it’s inevitable. You could give the presentation of a lifetime, all the right stats in the right infographics with perfect branding and slide animations, and you might still hear that dreaded two-letter word. But, here’s the thing, “no” doesn’t mean you’ve failed.

Here at TPC, we like to echo Nelson Mandela and remind ourselves that  “you don’t lose, you either win or learn”. Even if you don’t seal the deal, you’ve got updated statistics, a refreshed areas of need document, and a great presentation. And, you’ve built a relationship with folks who may become donors in the future and likely have other friends interested in giving to good causes (aka new prospects!). We also like to remind our coaching clients that “no” is “not right now” and generally speaking, if a prospect has taken a meeting (or several) with you, you’re already in and just need to figure out what the right ask of your prospect is.

The sooner you understand that a no isn’t the end of the road, the sooner you can use what you’ve learned and the connections you’ve made to pick up and keep moving forward.

5. The #1 reason people don’t give is because you don’t ask.

Mind-blowing, we know. Seriously though, if you’re thinking to yourself “Well, I ask for money all the time”, we invite you to do some self-reflection and ask yourself “Am I explicitly asking? Or am I just dropping hints and praying the donor TELLS me what they want to do?”

We hate to be the ones to break it to you, but a casual conversation with a prospective donor about upcoming campaigns does NOT count as asking for money. When we say The Ask, we mean explicitly asking your donor “Will you give $25,000 to help expand our mental health services?”

Here comes that lovely word again, groundwork. If you’ve got all the pieces in place, the donor should not only welcome The Ask, they should expect it. They know what’s coming, so don’t shy away from it. Remind them what you’ve already talked about, your levels of need, and the specific impact that their contribution will have on your organization and the community you serve. Be explicit and be intentional!

Important tip: when you’re scheduling that meeting to sign on the dotted line, make sure you’re up front about it. Don’t title the meeting invite “Catch Up Call” or something like that. Be transparent, and be confident in the fact that you’ve set up the shot and you’re ready to hit it out of the park.

If you’re still unsure about what all goes into the proverbial groundwork we continually reference, we encourage you to schedule a complimentary coaching session.

Additionally, Fundraising Academy has wonderful FREE workshops and a whole training series specifically focused on the Cause Selling Cycle aka the steps that will take you through the groundwork, The Ask, and beyond! Be sure to check out this webinar presented by our own Hannah Berger and Maggie Stillman focused on elevating your donor relations with strategic communications tools.

As always, we’re rooting for you! You got this!

– Team TPC