The Secret to Sponsored Ads That Feel Like Content (Not Interruptions)
How to Turn Sponsored Posts Into Must-Reads (Using Ann Handley’s “Pop Quiz” Trick)
Sponsored posts are one of the smartest ways to monetize a newsletter. But let’s be honest: most of the time, readers see the word “Sponsored” and tune out.
The challenge?
How do you highlight a sponsor in a way that keeps readers engaged—instead of feeling like an interruption?
Recently, I came across a brilliant example from Ann Handley in her newsletter Total Annarchy (Issue #195). She used a simple but powerful tactic that made me stop scrolling, pay attention, and actually click back into the email after getting distracted.
Here’s the best practice:
👉 Start with a curiosity hook—then reveal the sponsored post later.
Let’s break it down.
The “Pop Quiz” That Pulled Me Back In
At the top of the newsletter, Ann dropped a little “Pop Quiz” box:
That’s it. Short. Fun. Intriguing.
As a reader, I immediately wanted to know the answer. But she didn’t reveal it right away. Instead, she transitioned into her regular newsletter content (a smart play about Nike, NASCAR, and newsletters).
By the time I reached the sponsored section later in the email, I wanted to see the answer. The sponsor—Stockpress—was seamlessly framed as the solution to that question.
The result? The sponsored post felt like the satisfying payoff to a curiosity loop, not an ad interruption.
Why This Works
This approach taps into a few psychological triggers that make marketing work:
Curiosity Gap
Humans are wired to want closure. If you set up a question, our brains itch until we get the answer. Ann leveraged this perfectly.Pattern Interrupt
Instead of dropping into “here’s the sponsored content,” she created a playful pause (a quiz!) that felt organic to the newsletter.Reader-Centric Framing
The pop quiz was about me and my experience as a marketer—not about the sponsor. That meant I stayed engaged because it felt relevant before the product ever showed up.Story Arc
By the time Stockpress entered the picture, the ad felt like the punchline to a story, not an out-of-place promotion.
How You Can Use This in Your Newsletter
Here are a few ways you can borrow this when highlighting sponsors:
1. Start with a Quiz or Poll
“What’s the #1 thing creators say kills their productivity?”
“Which of these email subject lines had the higher open rate?”
“What do 67% of business owners admit they struggle with the most?”
Later in your newsletter, let the sponsor tie into the answer.
2. Use a Teaser Headline
Instead of “Sponsored by [Brand],” try:
“The answer to this week’s marketing riddle” [SPONSORED POST]
“Why we’re all tired of final_final_v3.doc” [SPONSORED POST]
“The sneaky productivity killer you haven’t thought about”[SPONSORED POST]
3. Make the Sponsor the Hero of the Story
Position the sponsor as the solution to the curiosity question you asked at the top. Readers get their answer and discover the brand in a way that feels natural.
4. Keep It Fun + On-Brand
Ann’s quiz worked because it sounded like her—clever, playful, and conversational. Your pop quiz or teaser should reflect your own style so it feels seamless.
A Few More Sponsored Content Best Practices
While the “pop quiz” hook is a standout tactic, here are some other ways to keep sponsored posts engaging:
Integrate sponsors into your narrative: Make them part of your regular storytelling style instead of an awkward add-on.
Highlight the reader benefit first: Focus less on features, more on the pain point it solves.
Offer exclusives or bonuses: A special perk for your readers makes the sponsorship feel more like a gift than an ad.
Use humor or metaphors: Ann’s “Final_final_NoForReal_v3” joke worked because it’s relatable and funny.
Final Thought
When I read Ann Handley’s newsletter, I didn’t just skim the sponsored post. I actively sought it out because she made me curious at the start.
That’s the kind of experience we want for our own readers: sponsorships that add to the value of the newsletter, not take away from it.
So, the next time you’re highlighting a sponsor, ask yourself:
How can I create a curiosity gap that makes the reader want to see the sponsor’s message?
How can I weave it into my voice and style so it feels natural?
Because when done well, sponsored posts stop being ads—and start being some of the most memorable parts of your newsletter.
