Have you ever thought that annual giving is just a classic roller coaster? You might think I’m referring to thrill you get from the ride – but I’m thinking deeper about the science behind the ride.
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Roller coasters use a combination of gravity, inertia and momentum to propel riders through the track. If you look closely, the biggest hill is first. This is called the lift hill. The lift hill uses a chain or other mechanism to pull the cars to the top. Take yourself back to your last roller coaster ride. Do you remember the excitement and anticipation you felt slowly creeping towards the top? When you reach the top of the lift hill, the train is filled with potential energy – in fact the height of that hill has a direct impact on the rest of the ride. As the train tips over the top of the lift hill, gravity, momentum and inertia take over.

For a rollercoaster, the kinetic energy gained from the initial descent dictates how the rest of the ride will go. If the lift hill is too short, there will not be enough energy built up for the cars to make it through the entire ride.

In annual giving, the three months before the fiscal year start is our lift hill. This is the time where you should be looking ahead towards the next fiscal year and setting your plan. Setting the plan now allows time to ensure that your strategy can make an impact starting on day 1. Ask yourself:

• What key initiatives do I want to anchor my fundraising calendar? A good strategy typically includes a key initiative for each quarter (i.e. initial donor renewal, calendar year end, giving day, fiscal year end, etc…)
• Do I have the tools necessary to implement my strategy? The pre-fiscal year period is a great time to ensure that you will have the platforms and vendors needed to implement your vision.
• Do I have the staff needed to execute my vision? If you are adding new initiatives or expanding initiatives, you may need additional personnel or expertise to successfully implement.

Have you ever noticed how a roller coaster doesn’t just have a series of loops? It has turns, slopes and other elements to ensure that as the train moves through the track it can build up more energy. In annual giving, your plan should be like the rollercoaster and include more than just solicitation.

• Be Prompt with Stewardship. Thank your donors quickly to reassure the donor that their gift was received and appreciated. Always include a quick thank you (like an immediate email). You may also want to have larger “thank a donor” campaign included as part of a key initiative.
• Always be Cultivating. In annual giving, it is all about cultivation. Our goal is to influence donor behavior, encouraging them to climb the donor pyramid with increasing and repeating support. A key component of this is cultivation. Your donors should receive outreach intended to engage and keep them connected with your mission. You should ensure your magazine, website and social media also include strategically timed gifts-at-work examples.
• Space It Out. To avoid donor fatigue, be mindful of the donor view and ensure your plan includes adequate spacing between solicitation appeals to the same audience. When planning your 1st quarter initiatives, think about the timing and how closely that may match up with any fiscal year end audiences.

Another key part of any roller coaster ride is ensuring that all the passengers are ready for the ride. Amusement park attendants do final checks to ensure passengers are secure. As you look ahead to the next fiscal year, be sure that your prospects are ready for your outreach. Studies continue to show that fundraising campaigns utilizing multiple channels of outreach create more opportunities for potential donors to connect with your organization and have higher rates of conversion. Now is a great time to ensure that your prospects will be able to receive your omnichannel outreach.

• Enrich The Data. Send key prospects to data enrichment services to capture and verify demographic information like address, email and cell phone.
• Collect Donor Preferences. Ensure online donor forms and event registration forms include areas to provide preferred contact information as well as opt-in by communication channel.
• Update your CRM. Ensure demographic updates received through returned mail, email correspondence or phone outreach are updated in your CRM. Ensure your outreach CRM is compliance ready with spaces to store opt-in preferences by channel.

When I started out in annual giving, the running joke was that once the fiscal year flips, you wipe the slate clean and start all over again. But after two decades of leading annual giving fundraising strategy, I’ve learned that it is far from the truth. What you do in the final quarter of your fiscal year has a direct impact on the next year’s results. So, as you are looking ahead to next year, remember the importance of a good design. Have a strong initial climb with a mixture of loops, turns and slopes throughout the path.  And always ensure your passengers are ready for the ride!

​Melissa Derrick Adair

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As a college freshman, I responded to an announcement on the Honors College listserv (that may give you a clue how long ago this was) for a job talking on the phone to alumni. I thought this was a dream job. All I needed to do was talk to people and make money. As an extrovert who had been trained by her manners-minded Southern mother to “make good conversation” my whole life, I had no qualms about keeping the conversation going and making folks like me on the phone.

After becoming a student supervisor in the call center, I quickly realized that most folks needed more structure and examples of what to say to have success at building rapport in conversation. It was indeed an art. I’ve now spent a couple of decades helping to systematize and teach the process of successfully talking to someone new. Over the years, I’ve learned that the secret to great conversations is the same whether you're a college student, a seasoned fundraiser, or even a 7-year-old girl chatting with her great aunt. It all comes down to asking the right questions.

Questions help us connect and connecting with a donor is essential before you ever ask for a gift. The right questions remove roadblocks and pave the way for a strong, lasting relationship between the donor and your organization. People give to people they like. As a fundraiser, you’re the bridge connecting the donor to your institution. Your goal in a discovery visit is to listen, learn, and understand what truly motivates them.
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Bad rapport-building does more harm than good. Questions should always stimulate a lively back and forth. Think dialog, not monologue. The best questions also extract valuable information, make the donor feel appreciated, and naturally lead to the next step in cultivation.
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Here are my favorite questions to ask during a discovery visit:

The key to a successful discovery visit isn’t just asking great questions – it’s truly listening to the answers. Take notes, follow up thoughtfully, and use what you learn to deepen the relationship. Building real rapport makes every future conversation easier and more meaningful. When the time comes to ask for a gift, you’ll know exactly how to approach it in a way that aligns with their motivations and values.

What’s your favorite discovery question to ask donors? Drop it in the comments—I’d love to hear what works for you!
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Cheers!

​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!

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Every year in November, National Philanthropy Day would roll around and I’d sigh and say to myself: “Next year, I’m going to be ready.” I’d swear that I would plan ahead, write the emails, prep the social media graphics, and really celebrate the day with our donors.

Then February would roll around and I’d see adorable Valentine’s Day posts from other schools – “We ❤️ our donors!” – and then again on St. Patrick’s Day – “We’re lucky to have you!” And I’d think: Next year. Definitely next year.

Finally, last summer, I had had enough.

We blocked time, pulled out the project management software, and started building a full philanthropy calendar – complete with stewardship moments, giving day content, and awareness-based messaging. And now? We don’t miss those chances to talk about philanthropy. We show up with intention. And the best part? Once this year is done, we’ll already have an entire year’s worth of content ready to refresh and reuse next time around.

Honestly – it’s one of the best things we’ve done.

If you’re in higher ed advancement (and especially if your fiscal year starts July 1), now is the time to build your calendar for the next year – before you're juggling events, campaigns, and year-end appeals.

When you plan your giving-focused content in advance, you give your team the time and space to tie fundraising to moments that matter – national observances, cause-based awareness days, and your own institutional milestones. You stop scrambling. You start seeing results.
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Digital fundraising isn’t just about being visible. It’s about being intentional.

Start with the obvious ones: your founding date, commencement, homecoming, or the birthday of a beloved former president with a named scholarship fund. Then build out from there.

Here are a few ideas to get you thinking:

• World Gratitude Day (Sept 21) – a lovely touchpoint to show donor appreciation
• National Philanthropy Day (Nov 15) – a perfect moment to thank donors and highlight giving’s impact
• National Estate Planning Awareness Week (3rd week of October) – opens the door for gentle legacy giving education
• National Scholarship Month (November) – great for student stories, recruitment, and stewardship

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The more your calendar reflects your organization’s story, the more it will resonate with your community. These aren't throwaway posts – they’re meaningful messages that reinforce your mission and make giving feel timely and personal.

Use scheduling tools like Buffer, Later, or Hootsuite to plan ahead. Build Canva templates you can reuse year after year. And make sure someone on your team is tracking which content types drive engagement – not just likes, but actual clicks, gifts, or email signups.

Once you get into the rhythm of planning ahead, the content starts to build on itself – and pretty soon, you're not starting from scratch every year. You’re refining, reusing, and getting stronger with every cycle.
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You don’t need a massive team or a fancy agency. Just a plan, a few tools, and a commitment to showing up for your donors in meaningful ways.

I’ve done the heavy lifting for you  –  get your free Year-Round Philanthropy Calendar with dates organized by theme and by month and ideas for implementation.
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This curated list of dozens of dates is tailor-made for fundraising, stewardship, and storytelling – including giving days, mission-aligned observances, and the quirky holidays that make for surprisingly great donor content.

Just drop your email, and you’ll be able to download it instantly. Easy.
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One calendar. A year’s worth of opportunities to show up, connect with your donors, and tell the story of your mission.

What dates are important for your messaging and content throughout the year? Let me know in the comments.
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Cheers,

​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!

If you liked this…

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• Kickstart the Year: Setting Annual Giving Projections for Success