Beyond the Ask: How Alumni Magazine Writers Turn Engagement into Support (and What Newsletter Writers Can Learn From Them)

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Before I became a full-time freelancer and newsletter publisher, I worked in alumni relations at the University of Chicago in a department that has received multiple awards for its work in this field. It was a formative experience to learn how to deliver these types of communications to a discerning audience and find various ways to say, “Aren’t you glad you’re a part of this community? We hope you show you’ll support us with a donation!” And since the University of Chicago is known for its high intellectual rigor, the writing had to be top-notch.

Take the time to read a good alumni magazine, and you’ll notice that these publications use various storytelling methods to entertain you, update you on campus news, and, of course, entice you to send in some money to show your support.

Sound familiar? Your newsletter probably does a lot of the same things.

It’s no coincidence that what I learned in that job at UChicago helped me launch a successful full-time freelancing career and gave me skills I put to use today in my own newsletter.

Last year, UChicago’s Mary Ruth Yoe, a giant in this space, retired from her role in the department, and that got me thinking about the parallels between the newsletter world and the alumni magazine world. So, I reached out to Yoe and several other former UChicago colleagues to figure out what newsletter writers can learn from alumni writers. 

Unlike these writers, you’re probably not trying to get your mailing list to fund buildings or faculty chairs or leave money to you in their wills, but you can still learn a lot from them about building loyal readers and convincing your audience to support your work.

Don’t try to be “everything to everybody”

I didn’t go to the University of Chicago, but working there helped me understand what kind of tone they use when speaking to their alumni, staff, and students. It’s a voice that’s intelligent and not afraid to show it. Interested in big ideas. Not afraid of controversial topics. Witty, with a hint of toughness that comes from attending a school where the average temperature each January is a balmy 23 degrees Fahrenheit. 

We say this again and again at Inbox Collective: If you want your readers to read your work, know them. Talk to them. Don’t start from a place of just trying to get the most subscriptions or shares. 

I didn’t appreciate until I began working at UChicago how important it is to identify your audience and hone your voice for those readers. Working there made me more critical of some other alumni publications I received. What did they think I was interested in? What part of my identity were they trying to speak to? Did they care whether or not I enjoyed reading their campus news — or did they just want my money? That last feeling made me less likely to engage.

The key, I learned, is finding ways to use that voice to drive specific segments of your audience to take action. Jeanie Chung, now a content writer at Discovery Partners Institute, was formerly a lead development writer at UChicago. She told me about when she tried to be “everything to everybody.” 

“You don’t want to do that. It’s not realistic,” she said. “For successful marketing, if you were trying to get people to do some specific thing, you work from the assumption that there’s a specific group of people who are going to be interested in this. You want to talk to those people, and not the widest possible version of what that could be.”

Show your supporters what their money pays for 

Alumni and development writers ask for financial support in myriad ways, including direct appeal letters, capital campaigns, fundraising emails, and magazine articles that don’t explicitly ask for money but indicate the school is worth supporting. 

Chung told me that one of her preferred ways of requesting donations was to tell readers exactly what their support has done for the university. For instance, “‘We provided scholarships for 100 people who were the first generation in their families to go to college. Your support makes this possible.” 

“I think that’s a way of asking for money without asking for money,” Chung said. “It’s a little bit less baldly gross than saying, ‘Please give me money.’”

So, if you ask your newsletter subscribers to support your work, take a moment to talk about what they’re paying for. Perhaps it funds the articles you write, the resources you need to do your work, or the team you’ve built. And if they love the community your newsletter offers, let them know it wouldn’t exist without their support. 

Tailor the marketing ask to the specific reader

Betsy Station, now a freelancer, learned the importance of personalizing her call to action, or CTA, while helming Tableau, UChicago’s Humanities publication.

Readers who’d never given before would be asked to “make a gift,” while existing donors would be asked to “renew your gift.” There were other variations on that, too: “We hope you’ll give a thousand dollars or more,” for a first-time donor, compared to “We hope you will consider increasing your support to $2,500 this year” for a long-time supporter.

There were other ways to personalize the CTA as well. At UChicago, Station told me, she might adjust the ask based on whether the recipient had a reunion that year or whether they were what they called a “participation donor” — someone who gives a small amount but gives consistently because they love their former school so much. A bit of progressive profiling — learning about your audience over time and adding more data about themselves or their interests to their profile — might help you deploy a similar tactic with your newsletter.

Two fundraising tactics consistently worked at UChicago and may also work well for newsletters like yours:

1. Put the “you” in it — That doesn’t mean you, the writer. It means “you,” the recipient of the letter. Tell them how they are helping and what their support does for the institution. 
2. Keep it brief — “The paragraphs have to be short,” Station said. “You have to give people bite-sized things for the eye to catch onto. if it’s too long and the paragraphs are too long, no one’s going to ever look at it.” If it doesn’t capture their attention, it certainly won’t lead to a donation.

Take chances with your content

Most alumni publications include boilerplate items about new faculty, awards the university or alumni have won, major gift announcements, outstanding sports achievements, and of course, alumni news. That’s fine for something to skim through and throw in the recycling bin — but what if you want to create something that people actually look forward to reading? 

It’s certainly easier for a well-funded staff to plan a quarterly magazine than a newsletter publisher to come up with ways to delight audiences on a daily or weekly basis. But sometimes, especially if you’re struggling with a strenuous publication schedule, your content may start to feel tired. Yoe’s advice: Don’t be afraid to be playful, to find new ways to tap experts in your network, and to find intelligent, thoughtful ways to probe spicy subjects that will get your readers talking.

“You can’t please everybody all of the time,” Yoe has advised alumni publishers. “And trying to do so makes for a dull publication. A publication that never upsets a reader is a publication that isn’t being read.” 

She doesn’t advocate for offending your audience on purpose, “but rather a take-a-chance, drive-something-new, don’t-always-play it safe approach,” she said. “When you have more fun, so do your readers. You’ll learn from each other.” At UChicago, that meant that one issue, you might read about a controversial speaker appearing soon on campus, and the next, you’d see a feature story about the messiest desks at the University. (“We got lots of letters from people who told us about other messy offices we’d missed,” Yoe said.)

Don’t half-ass headlines or subject lines

Working in the offices at UChicago is where I learned the value of taking your time to think of a good headline and not just dashing off some descriptive but boring words. It doesn’t matter how good the content is inside the magazine — or the newsletter — if the headline doesn’t grab the reader.

Yoe shared with me a presentation she’d given on coming up with non-boring headlines. A few of her takeaways work for both the alumni magazine and newsletter worlds:

• Be careful what you emphasize — Stealing from the lead bores the reader before they get hooked on the story. They read your great phrase and then, two seconds later, they get to read it again. Stealing from the finish, on the other hand, disappoints the reader. They’ve made it all the way through a piece only to find not dessert but a second soup course. No, thank you.
• Embrace the power of the subhead — or, in the case of the inbox, the preheader text.
• Write headlines early and often — Think about headlines while walking the dog, loading the dishwasher, and while writing or editing the piece. Don’t wait until right before publication to start brainstorming. Keep a running, written list of what you come up with as you prepare to publish.

Thank your most loyal audiences

Alumni publications can take this tactic to an extreme. “At Northwestern, they do something that’s anachronistic in a way,” Station said. (She worked as a senior writer at Northwestern after UChicago.) “They put out a print honor roll that they mail to people that’s packaged as an impact report.” She describes it as a heavy, beautifully printed piece with lots of writing, lots of photography, and a long, long list of everyone who gave a thousand dollars or more.

“It’s something like 12,000 people,” she said. “They don’t make a single ask in the whole publication. They thank people, they show them photos, and they remind them of the exclusive benefits they get from being part of this community.” Naturally, an envelope for placing donations is included with the book, and Station said the honor roll elicits “so many gifts. That’s a thing that I think is nice to do with development writing. You have to give people something because otherwise it’s just, like, “Us, us, us, us, us. Give, give, give, give, give.”

If you have thousands or even hundreds of supporters, it’s probably impractical to replicate this type of honor roll in email form, but maybe once a year or so, you can give thanks to your longest-running supporters, or your founding members, or your top commenters, with no strings attached. Or maybe you want to make space within your regular newsletter to thank new paying subscribers, members, or donors for their support. As other readers see those thank-yous, they may decide to join in and support your work as well.

Check out what your colleagues are doing

At our weekly editorial meetings at the University of Chicago, Yoe would spread out a collection of alumni magazines from other institutions she received, and we’d pass them around for discussion.

It was helpful to see what other publications were running; was it boring, interesting, fun, good-looking? It was a great way to get ideas for our own stories or ways to put our own spin on them. “If School Y does a story on its mascot, why not do an item on your mascot — even answering the questions you wish School Y’s magazine had asked?” Yoe advised. She encouraged us to take a look at industry publications like the Chronicle of Higher Education. “Take a trend piece and show how it applies to your institution,” she said.

Moreover, it was helpful and validating to speak with colleagues about the challenges we faced that were particular to our role (like faculty who wanted to take all the fun out of juicy quotes to make them sound more academic, or directors who wanted a “story” on a new school initiative that hadn’t actually been launched yet.) That was a preview of the importance of setting aside time to touch base with other newsletter writers. They know the specific pain of publishing a newsletter, and you may find a solution to your problems by talking to your colleagues — or, at the very least, feel relief in knowing it’s not just you. 

Above all, send out good writing

I thought I was a pretty strong writer when I got the job at the University of Chicago, but little did I know how much I had to learn! We were forbidden from using meaningless descriptors like “unique.” I learned that chunks of block quotes were a boring no-no. Every piece of writing needed to be reviewed by at least three people (editor, proofreader, director) before it got to any alumni, and even before you shared it internally, you needed to ensure the story was spell-checked, titles were formatted correctly, the Oxford comma adhered to, the graduation years double checked, and so on. 

UChicago alumni took pride in their intellectual rigor, so we communicated with them with an accordingly high level of respect. No, your newsletter writers probably won’t give you a hard time if you accidentally send out the odd typo or overlook some long-dead economist. But they will start to skim if you fail to edit, aren’t discerning about your prose’s purpose, or just send out a copy-and-paste job. If you send out high-quality writing, your audience will feel respected, respect you, feel engaged, and support you in return.