Fundraisers, Go Into 2026 With the Courage to Know Your Donor and Ask For What You Really, Truly Need

I’ve known and learned from some great fundraisers in my time.

And I’ve known some who fundamentally misunderstood their roles. Who are so intent on getting to yes, so laser-focused on bringing home the money, that they forget what fundraisers really are: honest brokers. 

We occupy that critical liminal space between a nonprofit and a philanthropist, facilitating conversations, understanding, and – eventually – collaboration. Or, at least, that’s the delicate work we’re supposed to be engaging in, the kind that depends on honesty, creating common ground, and achieving clarity about each other’s passions and goals.

When we counsel nonprofit CEOs and development leaders, we focus on a mindset shift – reframing the practice of fundraising so it aligns more with the much more effective broker model. 

Here’s how.

Let go of your insecurities, embrace curiosity

Before we even start to forge relationships, we have to get out of our own way. It’s easy to get deep in our own heads and insecurities when talking to philanthropists whose net worths are millions or even billions for the first time. But it’s also our literal job to do just that – talk to the donors – and to remember they’re people first and foremost. They have families they care about, personal hobbies and interests, professional pursuits, favorite sports teams, music, movies, and books, etc., etc.

Be curious and courageous. If you’re at an event, don’t assume that Donor X is more interested in chatting with a wealthy peer than she is with you. Donors may actually be tired of talking to the same people about the same topics at every event. In fact, chatting with someone new – like you – may feel like a welcome breath of fresh air. And if you find yourself struggling with what to say, fall back on what you’d open any new conversation with. What brings you to the event? What connects you with this org? How do you know so-and-so?  Genuine interest is the fuel that starts a genuine relationship.

Instead of offering a menu, set a common table

Too often, fundraisers just sell to the donor. Here’s why you should love Organization X. If you give at this level, you get our thanks! If you give at this level, you can come to our gala! If you donate at this level, you’ll get inducted in Our Very Important and Exclusive Giving Circle. 

The trouble is, no serious philanthropist wants to be sold a menu of things. Instead, set a common table; that’s the honest broker’s way.  Even as you’re sharing about the organization’s ambitions, you’re focused on finding out their ‘why.’ Who are they? What motivates them? Why give now? You can also share a bit about the organization’s ambitions.

Together you’re working to identify where you share a mutual appetite for growth. But the main ingredient is time (and certainly not a menu!).

Triangulate what you know and tailor what you offer

The more you can authentically get to know a donor, the more helpful you can be. 

If you know, for example, what life stage they’re in, you can begin to see what’s animating their drive to give, what may constrain giving, and what may enlarge their gift. For instance, someone whose children are heading off to college may be more selective and restrained about their pledges than those who are entering their golden years intent on ensuring an enduring legacy. 

You can then factor in those considerations in advance – plus how much they’ve given before and to what causes – before you lay out ways they can work together with the nonprofit. That kind of thoughtfulness removes friction and makes it much easier for both a donor and an organization to collectively imagine the art of the possible. 

When the time is right, ask big

Don’t pull your punches. Don’t go incremental. When I ask, I really go for it. I don’t waste a donor’s time with meaningless chitchat. I respect them enough to come to the point quickly. In the first four minutes, I say, “I’m doing something really important and I need to fund it to the tune of $20 million dollars. Could you consider a gift of $1,000,000?” 

Then I let them know I’ll be quiet until they have an answer and we can spend the rest of the time talking about why or why not. This strategy is respectful of the donor because I’m:

• Getting right to the point so we don’t waste time – we’ve already built common ground and we know why we’re connecting at that point in time

• Emphasizing our mutuality: we share the same desire to do something important and impactful

• Asking for what I really need versus nickel-and-diming them to death – we should not be making decisions for our donors in advance (“They’ll never go for it at that level”). Your donors work with big numbers; it’s not scary for them like it is for you.

Even if they don’t fund at the requested level, the odds are greater that you’ll still receive a higher donation than anticipated. 

Courage is bidirectional

Inasmuch as you need to access your bravery with a donor, you will also have the need to deploy it internally as well. Sometimes nonprofit leaders don’t want to hear that their vision for a donation isn’t actually shared by, well, the donor. As the honest broker, the link that connects the two, you must say, “That is not what this philanthropist wants. I think they’ll respond more to ABC.” Always come confidently with a strong alternative recommendation, but don’t be afraid to push back.

Know too that you may not always be able to make the linkage work. I once was working with a nonprofit and knew that the donor in question was ready to make a big gift – much more than anticipated – if the organization was equally ready to swing big. When I took it back to the CEO, the answer was no. It was immensely frustrating but sometimes, that’s what happens. Occasionally, nonprofit leaders will get cold feet. Concerned about misalignment, nervous that they won’t be able to deliver, fearful of disappointing a philanthropist hero, the reasons why are endless. Ultimately, however, it’s your job to help put the deal together, but you are not the final decision that gets it over the line.

Remember: in general, being brave and genuine are the two ingredients that seem to resonate with philanthropists the most. And when we hit those grace notes really well, our donors continue to stay with us – because they see the mutual opportunity to create something extraordinary together and they get to see the progress unfold and continue.

With that context, who wouldn’t want to keep going?