Staying in touch with donors all year long is crucial to keep supporters connected to the mission, make them feel valued, and lay the groundwork for strong year-end giving. But it can be hard to know how — or to find time — to build a 12-month outreach calendar, especially in a year that promises to deliver change and uncertainty.

The main thing is to have a plan in place, says Lori Woehrle, editorial director of Leapfrog Group, a firm that helps nonprofits with fundraising and marketing, but make it flexible so you can adapt if the landscape shifts. “No plan, more or less, equals no map going forward,” she says. “So if you want to end up somewhere, you need a map.”

The Chronicle spoke with several experts who outlined key steps to take and things to consider when crafting an annual outreach strategy. Here’s what they suggest to get the best results.

Plan according to your capacity.

Start with the end in mind, Woehrle suggests, including what you want to achieve and by when, which audiences you need to reach, and what milestones you should hit along the way. Plan at least 12 months ahead, she says, but you could look as far as 18 to 24 months out if you have the capacity.

If you’re a one-person shop and can only plan for the next six months, then do that, says Debbie Sokolov, deputy director for development and communications at the James Museum of Western and Wildlife Art in St. Petersburg, Fla. “Don’t put pressure on [yourself], because the most important thing is that you’re communicating,” she says.

Set realistic expectations.

After several years of unexpected challenges that hit the museum hard — including Covid-19 and two hurricanes — Sokolov says she tried to be much more realistic and conservative when projecting fundraising revenue for 2025. Uncertainty is just part of life now, she adds, so you must be nimble and flexible. But the more you plan, the easier it will be to adjust because you’ll have choices.

Define your goals and tie them to your nonprofit’s strategic priorities.

To start planning, identify your top three priorities for donor engagement so you can build tactics and messages that feed into them, says Chrissey Nguyen Klockner, a veteran fundraiser and consultant. For example, these might include increasing awareness of your cause, deepening key donor relationships, expanding your pool of support, or raising a specific sum.

Your outreach goals should be aligned with your organization’s strategic priorities, she adds, to ensure consistent messaging throughout the year.

Segment your donors.

Group supporters based on which kinds of communications you want to send them and how often, Sokolov suggests. If you’re new to segmentation, create three groups and give them an A, B, or C rating — such as major donors and prospects, event attendees, and small-dollar donors.

If you have monthly donors, consider putting them in their own group, Sokolov says, because they tend to be strong prospects for major and planned gifts.

Build the framework.

Identify the campaigns or moments when you know you’ll be reaching out to donors this year, Woehrle suggests, such as on GivingTuesday, through a monthly newsletter, or with a quarterly magazine. You might think of these touchpoints as the “building blocks” of your plan.

Also consider the cadence of your communications. It’s OK to get in touch with donors often, such as monthly, as long as you’re not always asking for money, she says.

Once you have a big-picture view of your calendar, look for gaps where you can plug in creative engagement and stewardship activities, suggests Jen Newmeyer, director of digital fundraising strategy at PBS. Involve other departments, she adds, so you can complement each other’s efforts and avoid competing or oversaturating donors.

Create a ‘menu of possibilities’ for outreach.

Don’t just share updates, Sokolov says. Communicate in ways that help build trust, reinforce the impact of donors’ generosity, and remind them that they’re key to your mission. “They want to feel connected and valued, so that’s what you want to do,” she says.

Sokolov keeps a folder where she adds items she could share with key donors when she wants to reach out to them, such as articles about the museum. She uses what she calls an “old-school” approach to make sure she talks with her A-list supporters every month: an Excel spreadsheet in which she plans communications for some months and pulls from her folder to fill in others as needed.

But make sure your messages are current, Sokolov says. If she found a strong, timely article related to the museum’s work today, she says, she would not wait to share it.

Plan consistent messages and focus on your goals.

Unless something dramatic happens, you shouldn’t need to change the focus of your messages very much in a year, Woehrle says. You might think of it as having a platform for your overall message, which should be tied to your work and objectives. “It’s really about the goals of the organization,” she says. “What they’re trying to do, how they’re doing it, and why it’s important and urgent — while being sensitive to the world around us.”

Don’t be afraid of sounding repetitive. People need to hear something seven times before they remember it, Woehrle says, and your nonprofit isn’t the only one they’re hearing from. So it’s critical to develop consistent messages and build on each one over 12 months to advance your goals.

“Avoid politics,” jokes Sokolov. Her organization is finding that messages about the “fragility of life” are resonating in the current environment, she says, because of the pandemic and recent hurricanes in Florida — “unexpected occurrences that have not discriminated in whose lives they touch.”

“Bring that into perspective at your organization,” she suggests. No matter what’s happening in the world, focus on bridging the gap between donors’ gifts and the lives they are helping to change, which is why they came to your organization in the first place.

Ask your donors what they want.

Check in regularly to see how they want to hear from you, what kind of information they would value, and how they would like to be involved, says Misty McLaughlin, founder of Cause Craft Consulting, which helps nonprofits strengthen fundraising and communications. An easy and inexpensive way to do this is to send an online survey, perhaps once or twice a year.

To get more detailed feedback, send a longer survey to a small group of donors who are very likely to respond, McLaughlin says, such as 50 of your longest-term supporters. Ask for 10 to 20 minutes of their time, she suggests, so you can try to better understand what’s driving their giving right now and how best to engage them.

Create useful content.

Use incentives like giveaways to fill gaps in your calendar or expand campaigns in ways that donors value, Newmeyer suggests. For example, she encourages PBS member stations to create an email series leading up to GivingTuesday to prime their audiences for year-end giving. The emails might be focused on recipes or meal ideas and include related trivia and online games. Everyone who participates enters a contest to win a box with cooking essentials or something similar.

You could replicate this tactic at different times of the year — for example, by providing travel tips or games for kids, like bingo or scavenger hunts, in the summer, says Newmeyer. But make sure the content relates to your mission. An animal shelter might offer incentives or summer ideas related to pets, and a health organization might talk about healthy eating in the summer or exercising in the winter.

Use email automation and A.I. to stay in touch more easily.

Create an email series with useful content related to specific dates or topics, Newmeyer says, such as reading lists with books by local authors or information about local history. These series could consist of three to four emails that people can sign up to receive at different times of year.

Sokolov’s team uses ChatGPT to improve their communications. They write the first draft, then use the tool to check for mistakes and get suggestions to strengthen it. For example, they might ask the bot if a message is donor-centric enough or ask it to help ramp that up. “You treat it like a person, and it’s made a world of difference,” says Sokolov, who took a class on A.I. through the Lilly Family School of Philanthropy.

When sharing a prompt with the bot, she’ll ask if it has any questions and offer feedback on what it produces, such as, “It’s not personal enough — can you make it more so?”

Prioritize communication channels and tactics you know will work.

Avoid the temptation to be on every platform because you think everyone else is, Woehrle says. Instead, go where the bulk of your donors are and focus on deepening engagement there. “Simplify, simplify, simplify, because it’s better for you to have a really high-quality channel than to be on many channels,” she says.

Once you’ve identified your key audiences, design outreach tactics based on what you know or think will work with each, says Farra Trompeter, co-director of Big Duck, a communications agency for nonprofits. To figure that out, look at your communications data and interview or survey your donors to find out what they need. For example, you might learn that a quarterly newsletter is enough for some, while others would like a monthly webinar.

Allow time for testing and evaluation.

Include in your plan a regular pause — perhaps once a month or quarter — to assess your efforts and consider what you should start, stop, and test, Trompeter says. This involves looking at what you did versus what you’d planned, what you learned, and what you might want to change, she says. Give yourself permission to stop something if it isn’t working, even if you’ve always done it. And if you’re not sure if you should do something new, try it for a test period before locking it in, whether three months, six months, or a year.

Also plan to do A/B testing of tactics and appeals, Nguyen Klockner says. If you want to try a new approach, such as using QR codes to link to a video, it’s smart to test that early in the year, she says, so at year’s end you can focus on things you know will work.

About every six months, “qualify” the donors you are reaching out to, Sokolov says, to determine if continuing to contact them is a smart use of your time. If you find you’re communicating consistently with certain people and they aren’t responding, agreeing to meet with you, or giving more, then take them off your list.

Prepare for the unexpected.

You don’t have to create a full emergency contingency plan if you don’t have the capacity, Nguyen Klockner says, but you should outline key questions to consider and steps to take if something significant happens in the world or at your organization. That might mean simply saying that leaders will meet for a 30-minute huddle to talk about how the organization, donors, and clients are being affected and how your nonprofit should respond.

It’s also a good idea to discuss what solidarity statements mean for your organization, she adds, and decide in which situations you’ll craft one and how.

Build up to the year’s end.

Consider your year-end campaign as the culmination of your annual strategy, Nguyen Klockner says, and think through the messages you’ll use, resources you’ll need, and the timeline for your campaign well ahead of time.

Gather those resources early, she suggests, so you don’t have to scramble during that critical crunch time. This might include language for your appeal, stories from donors or clients, photos or videos, or social-media posts. You could also develop a social-media tool kit with sample posts that you can share with your community to amplify your campaign.

And think about creative ways to make your appeal stand out from the rest, Nguyen Klockner says, and what you’ll need to do so. For example, one organization she worked with enclosed an ornament in its direct-mail appeal and asked donors to sign and mail it back to be included in a “donor tree.” The group then shared photos of clients with the decorated tree to get supporters’ attention and make them feel good.

Originally published Jan. 23, 2024. Updated Jan. 30, 2025.