Lingering Questions is one of my favorite things about writing this newsletter, because it’s an opportunity for marketers to talk directly to one another.
This year, a few clear themes emerged: yes, AI can help you be a better and more efficient marketer, but human connection is more important than ever; authenticity, even if it means you’re a bit unpolished, is preferable to perfection; and consumers across all industries are hungry for community.
| Lessons from 2025's Lingering Questions
Jackie Widmann, VP of marketing at Bero Brewing asked:
"Right now, it feels like so many brands are investing in beautifully produced, curated, experiential moments that are intended to drive awareness and shareability (and likely very expensive). How do you think new brands with limited budgets should approach this tactic and still manage to cut through the clutter?"
Kevin Indig, Growth advisor for Hims, Reddit, Toast, Dropbox & more, answered:
"In my experience, the highly produced moments matter at certain moments, like when customers consider a purchase, but what often catches their attention is the highly authentic, unpolished moment.
"That's why influencer marketing works. So, as a brand with a limited budget, I'd focus my budget on a few well-produced marketing assets (like videos of product images) and the rest on authentic, raw moments that build trust and curiosity."
Alicia Mickes, Senior creative director at Magic: The Gathering, asked:
"As marketing shifts from communication and storytelling to creating authentic cultural experiences, how are you or your company rethinking the role of Creative?"
Deesha Laxsav, Senior manager of brand marketing at Clutch, answered:
"Most recently, we've been testing more video content that's intentionally lighter-touch rather than investing in big, glossy productions. We're seeing that people consistently choose authenticity over stiffness. They want to hear directly from trusted experts in a way that feels conversational and relatable. For us, creative's role is to amplify real voices and experiences, not manufacture them."
Lisa Lozelle, Sr. director of state communications & engagement at Best Buddies International, asked:
"As a marketing thought leader, how do you see AI influencing strategic thinking and the creative process in brand building?"
Heike Young, Head of content, social, & integrated marketing at Microsoft, answered:
"AI is effective as a thought partner. Ask it to poke holes in your strategy and play devil's advocate. Also ask it to find additional research and data points you haven't considered. Those workflows can make your original ideas even stronger.
"All of that being said, I believe human creativity is more critical than ever, and I love seeing human fingerprints on the content I personally consume.”
Ashley Faus, Head of lifecycle marketing, portfolio, at Atlassian, asked:
"What tactics are marketers using to make their messaging stand out in a show floor filled with booths about AI?"
Jihan Donawa Gibson, Senior growth marketing manager at Swoogo, answered:
"The best way to get your booth to stand out against AI is to be human. Seems simple, but sometimes we forget that just building the booth doesn't mean attendees will come. People are craving human connection in this AI-driven time."
Jay Schwedelson, Founder of SubjectLine.com and host of Try This, Not That! For Marketers Only!, asked:
"What's one marketing belief you held five years ago that you've completely changed your mind about?"
Brian Morrissey, Founder of The Rebooting and former editor-in-chief of Digiday, answered:
"That in-person events would become less important. 100% wrong. In-person events are more important than ever.
"Humans are social animals and will always congregate. No matter what comes with AI, I do not believe the human species will throw in the towel on congregation."
Shareese Bembury-Coakley, VP of business development and partnerships at CultureCon, asked:
"I think nostalgia is something that's been overdone. I would love to know: What's a better way for brands to engage with communities or consumers that they want to connect with?"
Bryetta Calloway, Co-founder and CEO of Stories Seen, answered:
"I agree, nostalgia has become the easy button for connection. But real community is built forward, not backward. The better path for brands is participatory storytelling: inviting people to co-create the narrative rather than simply consume it. Communities don't want to be reminded of who they were; they want to be seen in who they're becoming.
"That requires marketers to move from campaigns to contexts, spaces where shared curiosity, lived experience, and emerging identity meet. Whether through localized storytelling, behind-the-build transparency, or platforming authentic user voices, brands can shift from 'remember when' to 'imagine with us.'
"Connection today isn't about familiarity; it's about alignment. The question isn't 'How do we tap into what people loved?' but 'How do we stand alongside what they're creating next?' That's where trust, loyalty, and modern belonging live."
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