Set the President and CEO Up for an Early Win
Start with a donor who already believes deeply in your organization.
Do you have a donor or volunteer who gives annually without fail? Someone who is reliable, supportive, and likely to say yes again? That’s the perfect place to begin.
Invite them to a meeting focused on vision and program updates. This allows your President and CEO to share the organization’s impact while also making a straightforward ask.
Early wins matter. When your leader experiences a few successful asks early on, their confidence grows. That confidence will make it much easier for them to step into larger and more ambitious fundraising conversations later.
Do the Proper Prep Work
A successful ask does not start in the room—it starts well before the meeting.
You may have heard the fundraising adage:
“The right person making the right ask at the right time.”
That advice is absolutely true, but I’ve always believed the real key is preparation. When everyone internally is aligned and prepared, the meeting itself becomes much more natural.
Once you secure the meeting, the preparation you do behind the scenes will determine whether the conversation leads to a successful outcome.
Be Clear When Scheduling the Meeting
Donors appreciate transparency.
Make sure the donor understands that the meeting will include a discussion about opportunities to support the organization. For example:
“Dr. Evans and I would love to meet with you to share an update on the African Penguins exhibit. We have some incredible opportunities for donors to be involved, and we can’t wait to share this update with some of our closest friends. Would you (and your spouse or partner, if appropriate) welcome a time to chat in the coming weeks?”
Always assume a spouse or partner may want to join the conversation. The donor will let you know if that isn’t necessary.
When scheduling, offer several dates and times that work for your team. It’s much easier for donors to select from options than to coordinate schedules themselves—especially when your donor and your President and CEO are both busy.
The sooner you secure the meeting, the better.
Decide Who Needs to Be in the Meeting
Set egos aside and focus on what’s best for the donor relationship.
Sometimes the VP or Director of Development doesn’t need to attend the meeting itself. If the gift officer has the strongest relationship with the donor, they may be the best person to join the President and CEO.
In some cases, a board member can also be helpful—especially someone who is comfortable making an ask or who has a strong relationship with the donor.
As a general rule, keep the meeting small. No more than three staff or board members should be present.
Hold an Internal Strategy Meeting
Even if they won’t attend the donor meeting, the VP or Director of Development should absolutely participate in the internal preparation.
This strategy meeting is where the team aligns on the big picture.
Discuss:
- The donor’s giving history and interests
- The amount you plan to ask for
- Whether the ask will be a specific number or a range
- Who will lead each part of the conversation
If the gift officer will not be present in the donor meeting, it’s especially important that they participate in this planning discussion. Their insight into the donor relationship is invaluable.
Prepare Talking Points and Roles
Before the meeting, decide who will handle each part of the conversation.
For example:
- Who will welcome the donor and guide the conversation
- Who will provide project or program updates
- Who will make the ask
Prepare simple talking points or a light script so everyone understands their role.
You don’t have to follow the script word-for-word, but having clear messaging ensures the conversation stays focused.
Also discuss how to handle potential pivots in the conversation. If you’re planning to talk about conservation initiatives but the donor wants to focus on the animals themselves, lean into their passion. The goal is always to connect the donor’s interests with the organization’s needs.
Make the Ask
This may sound obvious, but it’s surprisingly easy to avoid the actual ask.
Sometimes conversations become so comfortable that the team dances around the moment instead of addressing it directly. When the timing feels natural in the conversation, clearly present the opportunity.
If the donor says they cannot give right now, respect that response. Instead, ask whether there might be a better time to revisit the opportunity.
Fundraising is a long-term relationship, and every conversation helps move the relationship forward.
Leave With Clear Next Steps
Before ending the meeting, make sure everyone understands what comes next.
If you promised a proposal with naming opportunities, follow through quickly and deliver it by the agreed-upon timeline. Even better, prepare a proposal template ahead of time so you can turn it around quickly after the meeting.
In most cases, it’s best not to bring a proposal to the meeting itself. Allow the conversation to guide the next steps.
Follow up consistently—but thoughtfully. Persistence is important, but it should never feel pushy.
If it makes sense for the President and CEO to send the follow-up or personally deliver the proposal, plan that outreach for a specific date.
Involve the President and CEO Beyond the Ask
Fundraising isn’t just about the ask. Your President and CEO should be involved throughout the donor relationship cycle.
That includes stewardship and cultivation.
Consider assigning them a small portfolio of key donors. A gift officer should still manage the relationships, but the executive leader can play an important supporting role.
Review activities with them once a month and provide a short weekly list of outreach opportunities. Keep it manageable—perhaps three actions per week.
These might include:
- Sending a birthday card
- Calling to congratulate a donor on a milestone
- Sending flowers after a surgery or major life event
- Thanking a donor after a gift
Small gestures from executive leadership can make donors feel incredibly valued.
And when donors visit your organization, make sure the President and CEO knows about it. Even a quick stop-by to say hello can leave a lasting impression.
The fundraising team’s role is to make these moments easy for the President and CEO by planning and coordinating the details.
Final Thoughts
Involving a President or CEO in fundraising doesn’t have to feel overwhelming. With thoughtful preparation, clear roles, and a focus on donor relationships, executive leaders can become powerful partners in the fundraising process.
When development teams and leadership work together well, fundraising becomes what it should be at its best—meaningful conversations with people who care deeply about the mission and the impact an organization is making.
