Your most important fundraising relationship isn’t with a donor – it’s with your CEO.
Whether they’re the face of the organization to your biggest donors or a hesitant fundraiser you draw in strategically, you need them by your side – and there are a few roles they play that are hard to substitute with anyone else in the organization.
But of course, most nonprofit CEOs don’t enter the corner office through the fundraising door. For every born fundraiser (or former CDO) who ends up in the top job, many more come from other parts of the organization and have to build their fundraising skill set along the way.
We’ve seen every way the CEO-CDO working relationship can struggle, and we’ve heard every version of the frustration that can build up on both sides. Usually, it manifests as a kind of stuck-ness: meetings and decisions postponed, donor contacts that don’t happen, coordination and communication that stop flowing.
But we’ve also seen countless ways that CEOs can thrive in their fundraising roles with the expert partnership of their CDOs.
The good news is that there is no single fundraising archetype that every CEO must be browbeaten into. (That wouldn’t work anyway!)
And there are lots of workable ways to get your CEO-CDO fundraising flow unstuck. Here are our top seven:
Whatever their background, every CEO brings something to the table that can serve them well in fundraising. Some are natural storytellers; others are vision-setters. Some thrive in high-stakes conversations; others build connection through gratitude and recognition.
Rather than forcing a single model of “how the CEO fundraises,” start from the things they do most naturally—and pair them with the right partners to fill in the rest.
Every CEO has a few fundraising moments that don’t feel like work. Maybe it’s calling a kid who raised $300 with a lemonade stand, or picking up the phone to thank a donor for a seven-figure commitment. Maybe it’s nailing the speech or presentation that gets the whole room excited about their vision.
When leaders get to spend more time in those moments, their overall engagement tends to follow.
It’s lonely at the top – especially when you find yourself playing a high-stakes role outside what you consider your primary expertise.
CEOs often have fewer safe spaces to process uncertainty, rehearse difficult conversations, or reflect on fundraising missteps. An advisor or coach, formally or informally designated, can provide that space in a way staff relationships sometimes can’t.
When your CEO clocks in for a fundraising shift with you, they’re probably coming in hot from something unrelated but important, dashing out a quick response to a second thing, and trying not to think ahead to a committee meeting on a third topic that starts right after.
The greatest gift you can give them is a clear objective—here is how we win in this meeting/conversation, and here is the most important part for you to do—and a short set of talking points to start from. You probably already know what kind of messaging prep works best for them (bullets, themes, occasionally a fuller “script”), and even a little bit of guidance delivered at the critical moment goes a very long way.
Don’t just bring them in to push through the hard parts – let them feel the wins that make it worth it.
That might mean having them join for the meeting where you get to hear “yes” on a big ask even if it’s a foregone conclusion and their involvement isn’t strictly necessary. It might mean lining up smaller “yeses” to build confidence and momentum for the bigger ask to follow. It might mean asking them to make the final pitch for the proposed campaign name so that they can hear their most influential board members say they love it and are ready to lean in.
As CDO, you’re usually going to meet donors where they are (but of course!)—but when your CEO is involved, you’ll often be in the position of inviting donors to a meeting, event, or experience.
That means you can find the setting and setup that your CEO thrives in and build a repeatable strategy around it that becomes almost automatic for them:
Individual conversations over coffee. Site visits and tours. Small-group luncheons or salons. A conference-room conversation with a deck on screen that they learn like the back of their hand.
Find the one or two setups that bring out their best, and see how many of your CEO’s donor contacts you can turn into “home games.”
Finally, a common pressure point: expecting CEOs to solicit their close friends or peers.
Discomfort on this score is legitimate. In these cases, leadership can play a more effective role as cultivator, connector, or steward—while another partner handles the solicitation itself.
Whichever of these tips you reach for, they all share a common spirit:
Start from what works, get some wins, and build from there.
Your CEO isn’t going to turn into a duplicate CDO overnight, and you don’t actually need them to. But if you work together closely and build around the strengths that have carried them so far, you can start getting the kinds of wins that build momentum, capability, and engagement.
The CEO who starts the campaign as a hesitant fundraiser can emerge as a fundraising force – and the CEO-CDO relationship that starts in the mud can become a perfect pair.
We’re ready to invest in your success. Are you?
