Lingering Questions is one in all my favourite components of the Masters in Advertising e-newsletter, as a result of it’s a chance for entrepreneurs to speak straight to at least one one other.
This 12 months, just a few clear themes emerged: sure, AI will help you be a greater and extra environment friendly marketer, however human connection is extra necessary than ever; authenticity, even when it means you’re a bit unpolished, is preferable to perfection; and customers throughout all industries are hungry for group.
We’ve rounded up all of the questions entrepreneurs requested one another within the final 12 months:
April Sunshine Hawkins, Advertising and communications chief
“What heat reminiscence involves thoughts whenever you hear these three phrases: artistic, curious, brave?”
Irina Novoselsky, CEO of Hootsuite
“I’ve spent the final 12 months targeted on constructing significant relationships on LinkedIn — sharing private {and professional} experiences to create real connections. Every of those phrases have formed this journey: staying interested by what my viewers cares about and desires to study from me, experimenting with artistic methods to share my expertise and interact with others, and embracing the braveness it took to get began and be susceptible.
“Because the CEO of a social firm, I acknowledge the transformative energy of social media. It drives pipeline, builds connections, and ensures your voice shapes conversations which might be occurring with or with out you. However what’s much more highly effective is the influence the relationships constructed by way of social can have outdoors of the digital world.
“A reminiscence that stands out is the primary ‘IRL’ dinner I had with a advertising chief I linked with on LinkedIn, after months of partaking with one another‘s content material. What began as a digital connection has since grown into a real friendship (and lots of double dates with our husbands!) — and it’s all because of social.
“To any entrepreneurs studying this that could be hesitant to get began, let this be your signal: Make the leap into posting. You do not know what new friendships you might be lacking out on.”
Learn extra: Gen Z is popping this CEO’s enterprise mannequin the wrong way up
Novoselsky requested, “How do you strategy your private model on social media? Has social created significant alternatives or opened doorways for you professionally and personally?”
Preston Rutherford, Co-founder of Chubbies
“I strategy the non-public model piece by attempting to be precisely how I’m in particular person. I do not know find out how to do the rest.
“And sure, it has opened infinite doorways, not least of which is the chance to speak with [Masters in Marketing]!”
Learn extra: Chubbies’ co-founder warns: Don’t get hooked on the efficiency advertising drug
Rutherford requested, “What’s your favourite film that you simply’re embarrassed for anybody to learn about?”
Anna Engel and Nathaniel Gaynor, Director of brand name, content material and tradition; Sr. advertising supervisor, model partnerships at McDonald’s
Gaynor: Eurovision Music Contest: The Story of Hearth Saga
Engel: The Princess Diaries
Learn extra: Past the Golden Arches: How two McDonald’s entrepreneurs win Gen Z
Engel and Gaynor requested, “What model do you suppose is taking daring dangers to attach with Gen Z right now?”
Jeff Wirth, Co-founder of the Interactive PlayLab
“Occasion At Anna‘s is an organization pushing boundaries by creating interactive and immersive experiences that resonate with Gen Z’s love for storytelling and social engagement.
“Their tasks take daring dangers by incorporating real-time viewers participation, unconventional venues, and dynamic, unpredictable narratives. By embracing themes of id, group, and collective storytelling, they craft extremely shareable and deeply private experiences that redefine what theatre might be for a brand new technology.”
Learn extra: Marketing consultant behind Meow Wolf, Blue Man Group shares classes on pleasure, enjoying, and branded experiences
Wirth requested, “What’s a blind spot within the advertising world that, if addressed, would make folks’s lives higher?”
Eric Munn, Director of promoting at Chicago Transit Authority
“A significant blind spot within the advertising world is forgetting that most individuals aren’t as conscious of your model as you’re. Many manufacturers use messaging that already assumes folks know who you’re or what you supply. Be sure you’re clear about what your services or products goes to do to assist folks. Witty and crowd pleasing is enjoyable, however the conversion is in fixing folks’s issues.”
Learn extra: Advertising like a Castaway
Munn requested, “What’s a profession you’ve got all the time needed to get into however by no means have?”
Jennifer Waters, Co-founder of seven Determine Dojo and government sensei at Seigler’s Karate Middle
“Actually, I all the time needed to do what I am doing right now! No different careers I’d wish to have!”
Learn extra: Be a knockout in small and native enterprise advertising
Waters requested, “What’s one advertising mechanism that may generate essentially the most income rapidly for a startup?”
Erin Quinn, The Unique Pickle Shot
“I do know it‘s annoying to say ’it relies upon,’ however my advice for fast income progress would probably differ relying on the startup.
“For instance, paid social is more likely to be a cost-efficient and impactful selection for a budget-friendly DTC skincare model focused in the direction of Gen Z. (There is a purpose that paid social is the primary and solely paid media that many manufacturers spend money on!)
“Promo codes, rebates, and couponing might be an necessary add-on to mentioned marketing campaign, as these ways present an additional incentive for conversion and you should use redemption as a KPI.
“Irrespective of the enterprise mannequin, my most necessary ‘do that earlier than the rest’ advice can be to spend time in your client goal, positioning, and model id growth so that you’re concentrating on the appropriate folks in the appropriate place with the appropriate messaging and inventive. It will not drive income within the quick time period, however it would prevent cash and drive income in the long term.”
Learn extra: How this small startup outperformed a stalling business
Quinn requested, “What’s essentially the most memorable commercial (industrial, print advert, OOH, something!) you may bear in mind seeing, and why do you suppose it has caught with you?”
Alex Lieberman, Co-founder, Morning Brew
“The OG Greenback Shave Membership ‘Our Blades Are F*cking Nice’ industrial.
That spot hits on every little thing I search for in an excellent advert:
- It tells a narrative, which makes you FEEL earlier than you THINK.
- Its strategy is novel, which creates intrigue & makes you lean ahead (vs. lean again).
- It doesn‘t promote a product. It sells an emotion. And as soon as you’re feeling that emotion, you grow to be open to the product.It’s an advert disguised as leisure. One of the best advertisements make you’re feeling such as you‘re consuming ice cream, whenever you’re actually consuming cauliflower.
The spot drove 27 million YouTube views on a price range of $4,500, and I imagine is an enormous purpose why DSC in the end bought for $1 billion to Unilever.”
Learn extra: Morning Brew’s co-founder on the three channels that may win 2025 (plus, find out how to craft a voice that stands out)
Lieberman requested, “What are your ideas on the continued ‘attribution’ hoopla? And what’s the correct amount of attribution with out getting overly scientific/metrics-focused together with your advertising technique?”
Jackie Widmann, VP of promoting at Bero Brewing
“If you‘re constructing a brand new model from the ground-up, you don’t have historic knowledge to have a look at as you consider efficiency. We‘re doing every little thing that we are able to to mix a mixture of extra tactical metrics (i.e., gross sales of our merchandise throughout channels as we spend money on numerous advertising ways, how rapidly we’re rising our group and the way engaged they’re with the data we’re sharing with them, and naturally monitoring sentiment round every little thing that we are saying and do).
“One of the best factor manufacturers can do proper now could be to function with a linked technique and have a look at each second as a chance to be 360 – and actually analyze your leads to the identical manner.”
Learn extra: Be an addition, not a substitution: Classes from Tom Holland’s NA beer model
Widmann requested, “Proper now, it looks like so many manufacturers are investing in superbly produced, curated, experiential moments which might be meant to drive consciousness and shareability (and sure very costly). How do you suppose new manufacturers with restricted budgets ought to strategy this tactic and nonetheless handle to chop by way of the litter?”
Kevin Indig, Progress advisor for Hims, Reddit, Toast, Dropbox & extra
“In my expertise, the extremely produced moments matter at sure moments, like when clients think about a purchase order, however what usually catches their consideration is the extremely genuine, unpolished second.
“That is why influencer advertising works. So, as a model with a restricted price range, I might focus my price range on just a few well-produced advertising property (like movies of product photographs) and the remainder on genuine, uncooked moments that construct belief and curiosity.”
Learn extra: Reddit’s progress advisor on discovering your vertical-specific search engine optimisation technique
Indig requested, “What’s essentially the most underrated advertising channel proper now, and why do you suppose it deserves extra consideration?”
Lisa Lozelle, Sr. director of state communications & engagement at Greatest Buddies Worldwide
“For me, the present most underrated advertising channel is unsolicited mail. A well-designed print piece can break by way of the litter and make an influence.
“Folks save postcards from favourite non-profits that seize a mission second, connecting them to the trigger. They earmark pages in a well-designed catalog of merchandise they covet and are incentivized to buy with unsolicited mail items that really feel curated and private.
“Professional Tip: Mail is not useless — ask Gen Z. In accordance with a USPS survey, 72% of digital natives get enthusiastic about good old school mail. Give them one thing to carry on to.”
Learn extra: Model-building brilliance from Greatest Buddies
Lozelle requested, “As a advertising thought chief, how do you see AI influencing strategic considering and the artistic course of in model constructing?”
Heike Younger, Head of content material, social, & built-in advertising at Microsoft
“AI is efficient as a thought associate. Ask it to poke holes in your technique and play satan‘s advocate. Additionally ask it to seek out further analysis and knowledge factors you haven’t thought of. These workflows could make your authentic concepts even stronger.
“All of that being mentioned, I imagine human creativity is extra vital than ever, and I really like seeing human fingerprints on the content material I personally eat. For example, I’ve lately been swooning over all of the tiny artistic particulars in Severance.
“I imagine some AI-related adjustments in advertising will occur quicker than we anticipate, and others will occur extra slowly. Solely time will inform what falls into which class. So I am leaning into AI the place it is helpful for me, and never forcing it the place it does not appear useful.”
Learn extra: How Heike Younger makes use of humor to rework B2B advertising
Younger requested, “What’s a chunk of promoting recommendation you’d have given earlier in your profession, however you’d not give, as a result of how advertising has modified?”
Sonia Thompson, Founding father of Inclusion & Advertising
“Early in my profession, I’d have suggested entrepreneurs to spend time specializing in a singular model and actually investing in what you may do to ship a outstanding buyer expertise.
“It‘s not that outstanding experiences and powerful manufacturers aren’t wanted, however I discover spending an excessive amount of time there — particularly up entrance — prevents manufacturers from displaying up constantly. Right this moment’s world and customers transfer quick — and fairly frankly, customers would be the ones that information you on what makes a outstanding expertise.
“So, it‘s extra necessary now to point out up and let your voice, viewpoint, and what you stand for be identified. Refine your expertise over time, primarily based on suggestions out of your clients and the group you construct. That group and the belief they should have with you is difficult to construct should you don’t present up constantly. Do not fall into the entice of research paralysis.
“This is not a case for delivering poor high quality, however quite a case for manufacturers and entrepreneurs to do a greater job of being lively shapers and members of tradition as it’s occurring. Be related and memorable to customers in a manner that’s most valued and related to them. Your advertising and influence might be way more efficient because of this.”
Learn extra: Foremost character vitality: What Black Panther can educate you about inclusive advertising
Thompson requested, “How have you ever seen inclusion form the way in which advertising has been accomplished over the past 5 years, and the way do you’re feeling it would form (if in any respect) the subsequent 5 years of promoting?”
Jay Schwedelson, Founding father of SubjectLine.com and host of Strive This, Not That! For Entrepreneurs Solely!
“Over the previous 5 years, inclusion has shifted from a company checkbox to an important a part of how we strategy advertising and enterprise total (or a minimum of, it must be!).
“It‘s not nearly who seems in inventory images; it’s about who’s growing the technique, writing the copy, and making the choices.
“In our personal work, from digital occasions to newsletters to company providers, we have seen that when folks really feel seen, they have interaction extra, share extra, and keep loyal longer.
“Trying forward, inclusion will not simply form advertising, will probably be advertising. As AI continues to dominate content material creation, the power so as to add a human contact, making each particular person really feel acknowledged, revered, and understood would be the final differentiator.”
Learn extra: Attribution is rubbish, says this e mail knowledgeable. (Plus, 3 causes Jay’s a loser)
Schwedelson requested, “What’s one advertising perception you held 5 years in the past that you have utterly modified your thoughts about?”
Brian Morrissey, Founding father of The Rebooting and former editor-in-chief of Digiday
“That in-person occasions would grow to be much less necessary. 100% incorrect. In-person occasions are extra necessary than ever.
“People are social animals and can all the time congregate. It doesn’t matter what comes with AI, I don’t imagine the human species will throw within the towel on congregation.”
Learn extra: The expansion hack period is ending, in response to Digiday’s former editor-in-chief
Morrissey requested, “Will search engine optimisation be out of date in three to 5 years?”
Shelagh Dolan, Content material advertising lead at Quora for Enterprise
“Actually? Sure.
“Conventional, natural search engine optimisation has all the time been a problem — it required fixed analysis and upkeep with no assured returns, to not point out being beholden to an algorithm that might tank your technique at any second.
“AI Overviews and zero-click search have made it 10 instances more durable to drive natural visitors, and in three to 5 years, there might be no purpose for anybody to ever scroll by way of pages of outcomes to seek out themselves on a company-sponsored weblog publish studying a long-winded, H2-clad overview of an business subject — and I say this as a long-time content material marketer.
“I take into consideration how my very own information-seeking habits has utterly modified over the past 12 months with AI, from discovering fast solutions and technical troubleshooting at work to creating recipes and getting TV/film suggestions at dwelling.
“I don‘t have a technical background however I get a each day behind-the-scenes have a look at the AI product the Quora crew is constructing (it’s known as Poe, and it is a central place to entry each AI mannequin and create your individual custom-made bots). The most important shock has been how rapidly new fashions and capabilities roll out — bulletins and launches virtually each day.
“I feel entrepreneurs — most likely particularly B2B entrepreneurs — are hyper conscious of AI‘s capabilities and its influence on search engine optimisation, amongst different elements of promoting, but it surely gained’t be lengthy earlier than most of the people catches up and turns into accustomed to the deeply personalised experiences doable by way of AI.
“Quickly everybody will gravitate to their most well-liked technique of discovering and consuming info, whether or not it is scanning an AI Overview, messaging a chat app (which might already accomplish that way more than chat), conversing out loud with AI, or referencing a handful of trusted sources.
“In three to 5 years I feel we’ll be far-off from scrolling by way of SERPs and far nearer to a Her [the 2013 sci-fi movie in which a man falls in love with his AI] state of affairs.”
Learn extra: Does Quora work for advertising?
Dolan requested, “In addition to AI, what advertising tendencies or applied sciences are you retaining your eye on or planning to do this 12 months?”
Katie Parkes, Director of social, group, and buyer advertising for Apollo.io
“I am paying shut consideration to how knowledge storytelling is evolving, particularly as belief in conventional advertising claims continues to erode.
“The manufacturers standing out proper now aren‘t simply publishing content material — they’re displaying receipts. Buyer influence. Product utilization. Clear benchmarks. As social algorithms proceed to reward who’s getting essentially the most consideration, credibility is the brand new forex.
“However right here‘s the factor: credibility can’t simply be manufactured and is not all about numbers. It must be earned in artistic, human methods, so you might want to depend on actual voices.
“That‘s why I’m enthusiastic about creator-led and community-first B2B advertising — tapping into your energy customers, inside consultants, and group members to share the story in their very own phrases. We’re transferring away from polished model narratives and towards trusted people who deliver each experience and authenticity.
“It is not about saying extra, it is about being believed.”
Learn extra: Flip your energy customers into creators (and vice versa)
Parkes requested, “What’s one ‘boring’ advertising channel or tactic that is working manner higher than anticipated for you proper now, and why do you suppose that’s?”
Jay Schwedelson, Founding father of SubjectLine.com and host of Strive This, Not That! For Entrepreneurs Solely!
“Weekend e mail sends! E mail campaigns concentrating on director-level and above contacts are producing a 40% 12 months over 12 months improve in click-through charges. Not testing Sunday sends is leaving a brilliant invaluable alternative to interact with key folks after they have the time to actually dig into what you’re sharing.”
Learn extra: What you’re doing incorrect in your advertising emails (in response to an e mail knowledgeable)
Schwedelson requested, “You all the time say ‘create as soon as, distribute perpetually’ — what’s one piece of content material you’ve got milked longer than anybody ought to fairly admit? And why that one?”
Ross Simmonds, Founder and CEO of Basis Advertising
“One piece of content material I‘ve completely milked? A tweet I wrote in 2019 merely mentioned ’Create As soon as, Distribute Ceaselessly‘ and it was successful… It wasn’t even meant to be a flagship thought again then… Only a mind dump about repurposing technique. However I saved referencing it in talks, turning it right into a slide, a workshop, a tweet thread, the title of my ebook, a core framework for Basis.
“Why that one? As a result of the idea resonated deeply not simply with entrepreneurs, however with entrepreneurs, creators, and executives who realized they have been sitting on gold with out mining it. It gave folks permission to cease chasing new and begin maximizing what they already had. That message caught, and I have been doubling down ever since.”
Learn extra: Trash AI content, experimental budgets, and TikTok for B2B: Ross Simmonds unfiltered
Simmonds asked, “What’s one marketing hill you’ll die on… Even if the data or the trends say otherwise?”
Grace Wells, Creative director
“It‘s not about how big you are, it’s about how connected your audience feels.
“Buying followers is worse for your credibility than a small organic following. Avoiding events because they cost money robs you of essential customer interaction. Organic content and brand storytelling are what make conversion content work. I see so many brands get caught up in chasing an immediate conversion to scale as fast as possible.
“To get big you have to get connected to an audience that will champion your growth, and that takes soft skills.”
Read more: Make space for customers to see their business as part of yours
Wells asked, “What’s one thing you learned in your first-ever job that remains core to the businessperson you are today?”
Joy Gendusa, Founder and CEO of PostcardMania
“I learned that most people give 80% to their work and some give 100%. If you give 110%, you’ll be the best.”
Read more: 239% growth from… print mail?! Why you shouldn’t sleep on direct mail
Gendusa asked, “What’s one marketing strategy you think will be obsolete in five years?”
Maya Grossman, Executive career coach and CEO of Maya Grossman Group
“In 5 years content won’t be king.
“We‘re already seeing AI can generate ’good‘ content on demand (just spend 5 minutes on LinkedIn). What breaks through won’t be quality alone but distribution strategy, speed of iteration, strategic positioning and relevance. Your brilliant thought leadership won‘t matter if your buyer’s AI skips it for something faster, easier, or more emotionally compelling.
“Marketers’ jobs will revolve less around creating and more around matchmaking.”
Grossman asked, “What’s a trend everyone’s excited about that you think is overhyped or completely misunderstood?”
Brenna Loury, CMO of Doist
“Adding AI chatbots everywhere. *ducks for cover*
“Unless there is a very obvious use case, I feel that this is a lazy implementation of AI. Most companies need to think much harder about their users’ pain points before just slapping a chatbot onto their UI.”
Read more: Memorable marketing, visible mistakes, and a faster horse
Loury asked, “What is your favorite thing about marketing that can’t be easily measured?”
MacKenzie Kassab, Director of creative strategy at Rare Beauty
“The emotional connection. I love the way marketing can make people feel something. It could be inspiration, motivation, curiosity, nostalgia, or just a moment of joy. For us it comes down to self-acceptance and belonging. That connection drives everything we do, no matter how impossible it is to quantify (although I’m sure AI is trying).
“Helping even one person in our community feel seen and comfortable in their skin—I love so much about my work, but that’s really what gives it all meaning.”
Read more: Rare Beauty’s “anonymous insider” spills the tea on their new Substack
Kassab asked, “What’s your least favorite part of your job, and how do you motivate yourself to get through it?”
Max Miller, Founder and host of Tasting History
“My least favorite part of the job is the constant need for growth and more content. Whenever a video drops, YouTube gives me a ranking of how the video is performing in comparison with the last 10 videos. If it‘s a 1 out of 10, it’s a good day; if it‘s a 10 out of 10, my whole day is spent asking why people didn’t like it as much.
“The best way to motivate myself through that is remembering that I get to do what I love for a living — even on the tough days, that perspective keeps me going.”
Read more: Tasting marketing: What a viral YouTube star wishes marketers knew
Miller asked, “Have you found AI making an impact on your work at Condé Nast? If so, has it been a net positive or net negative? In many ways, the proliferation of AI content is making creating quality content, especially educational content, more difficult so I’m always curious how this new technology is affecting other fields.”
Sheena Hakimian, Senior director of digital consumer marketing at Condé Nast
“From a marketing and subscription standpoint, we’re excited to explore how AI can help us deliver more dynamic, personalized experiences on our sites. That said, the human touch is still the heart of our strategy, especially when it comes to brand voice and creative direction.
“The rise of AI-generated content has actually made high-quality, thoughtful content even more valuable. It’s easier than ever to pump out content, but much harder to build trust, credibility, and originality.
“At Condé Nast, our unique edge is still our storytelling and editorial integrity. AI, to us, is a tool to scale our voices around that, not replace it. So overall, I’d say it can be a net positive when used with intention. But like anything, it depends on how thoughtfully it’s integrated.”
Read more: Condé Nast marketing leader shares her framework for destroying your imposter syndrome
Hakimian asked, “You’ve built an incredible reputation for understanding Gen Z behavior and creating authentic, community-first content. In a world that’s constantly chasing virality, how do you balance consistency with creativity, and what advice would you give to brands trying to build genuine relationships over time, not JUST reach?”
Jayde Powell, Founder and head of creative at The Em Dash Co.
“Remember that there‘s a difference between consistency and cadence. Oftentimes I feel, especially as it relates to building community on social, that there’s this mentality that the more content you pump out, the more you engage with people — and the more beneficial it is for your brand. And I disagree.
“I think what people are looking for is a sense of comfort, a sense of home, a sense of familiarity. And that‘s what you can accomplish through consistency. Consistency is less about how much and how often you’re putting content out and more about the feelings that your audience will associate with your brand.
“So it could literally be something as simple as the style and the tone in which you communicate or create your content. It could be the visuals you use. It can be how you greet your audience when you post — those are the things that really build community.
“Think of it as like a relationship. You’re not in a relationship with someone just because of the amount of things that they do for you, it’s how they do it for you. That’s the same way it should be for your community as it relates to brands.”
Read more: Marketing without the cringe: Jayde Powell on Gen Z audiences
Powell asked, “What sparks joy for you?”
Ryan Atkinson, Founder and CEO of Spacebar Visuals
“Professionally, when you take a bet on something and it works.
“Personally, being with family, friends, working out, and reading books.”
Read more: Don’t just grow to grow: Real talk from a serial founder
Atkinson asked, “If you could only invest in one tool to help your company grow for the next three years, what tool would it be?”
Al Iverson, Industry research and community engagement lead at Valimail and deliverability consultant and publisher at Spam Resource
“Email deliverability is a land of best practices. Do’s and don’ts that we collectively tell people to stick to, but we can potentially become too complacent to stay within our lane, not challenge the status quo of how best to do something, whether it be connect with our audience or market a new product.”
Read more: Here’s why your next newsletter isn’t going to spam
Iverson asked, “What’s one email-sending habit or best practice you think we should collectively leave behind, and what would you replace it with?”
Lindsey Gamble, Creator economy consultant and creator of the Lindsey Gamble newsletter
“Relying solely on last-click attribution for measuring the success of influencer marketing is a mistake. Sure, tracking links and promo codes show direct sales, but creators play a much bigger role in awareness, brand building, consideration, traffic, and more, all of which leads to purchases down the line, even if the link or code isn’t used.
“We need to measure the impact of creators more creatively and look at the full picture, including content performance, website traffic, brand follower growth, search lift, share of voice, brand and sales lift studies, post-campaign surveys, and other methods to capture the true impact of influencer campaigns, otherwise you’re likely missing a ton.”
Read more: Why creator marketing works for any business
Gamble asked, “What’s a marketing strategy or trend that you think is widely overlooked but has high potential for impact right now?”
Brandon Smithwrick, Founder of Content to Commas
“One strategy I think is often overlooked is using social media to drive exclusive offers directly within the community you’ve already built. For example, teasing a promotion through Instagram Close Friends can give you a sense of traction before launch. Tools like ManyChat also make it easy to create DM-only offers that feel special and personal.”
Read more: “You can make money doing this?!”
Smithwrick asked, “What’s a creative hot take that will make a marketer second guess how they work with creatives?”
Alicia Mickes, Senior creative director at Magic: The Gathering
“In my experience, the business side (i.e. product strategists, sales and marketing managers) bring in Creative too late…often treating creative as the shiny gift wrap around the product strategy—but in reality, the creative is the product strategy.
“If you involve us only at the end, you‘re not getting design, you’re just getting decoration. Every time you hand us a baked plan and ask us to ‘make it pop,’ you’ve already cut the legs out from under what could have been a more powerful marketing campaign.
“Let creatives lead earlier! I always encourage working in groups: have early holistic campaign development conversations with key stakeholders from media, strategy, product, and creative. The future of marketing is all about experiences where creative execution is indistinguishable from brand strategy. If you still think of Creative as just a service department, you’re already behind.”
Read more: Why creative teams need the safety to fail, according to a senior director for Magic: The Gathering
Mickes 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
“At Clutch, we‘re making sure every content piece is supported by creative that feels rooted in real-life experiences. That means weaving in authentic perspectives from influencers and providers we quote, so the stories aren’t just polished narratives, they‘re reflections of what’s actually happening in the market.
“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.”
Read more: Why you should build relationships backward (and how)
Laxsav asked, “When it comes to building partnerships for CultureCon, how do you decide which people to collaborate with — whether that’s speakers, creators, or community leaders — to make sure they authentically represent CultureCon’s mission and resonate with your audience?”
Shareese Bembury-Coakley, VP of business development and partnerships at CultureCon
“At CultureCon, data is paramount to everything we do. So, we‘re not making assumptions about our audience, we’re not just coming up with ideas. We’re really letting that [data] inform everything that you see.
“So, the programming that you see being hyper-relevant? Our communities told us what they wanted, the brands that they like to engage with, the speakers they wanted to hear from, and we listened to them.
“I think a lot of brands and communities are sometimes trying to go against the grain, trying to push something on their audience, and it’s not what they want. We evolve and iterate [based on data], and that’s why the brands and the community and the speakers can come out and have a great time.”
Read more: It’s all about you
Bembury-Coakley 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
“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.”
Calloway asked, “As marketers, we often talk about authenticity and alignment but those words can become buzzwords fast. How do you ensure your team stays connected to real people and not just the performance of connection?”
Katie Miserany, Chief communications officer and SVP of marketing at SurveyMonkey
“You absolutely must know what your customers care about and want from you. I think a lot of brands today want to be “cool” and that’s contributing to the great flattening of brands and content across the ecosystem right now.
“At SurveyMonkey, we don’t aspire to be cool. We want to be the lovable nerd who you want to partner with in your high school chem lab because you know we’ll do all the work and make you look smart. This is how you differentiate today: know the value you provide in your customers’ eyes and maximize it in everything you do.”
Read more: Why SurveyMonkey’s marketing leader says your foundation is broken
Miserany asked, “Every leader must justify marketing and brand investment with hard numbers. How do you functionally bridge the gap between creative, intangible brand value and tangible financial outcomes, and how do you justify that brand investment to key stakeholders?”
Ashley Judge, Executive director at Destination Salem
“In destination marketing, our work sits between numbers and imagination. We’re here to drive economic value for residents and small businesses, so we measure everything: visitation, spending, seasonality, excise tax. But the way we get there is by creating a bit of fantasy. People don’t visit because of data; they visit because they’ve been pulled into a story about a place. Our creative work builds that story, and when it works, you can see it in the numbers that follow.”
Read more: Marketing is removing barriers: Lessons from a destination marketing expert
Judge asked, “What’s something your team does purely out of love for the user — not metrics, not growth, just because it feels right?”
Ashley Faus, Head of lifecycle marketing, portfolio, at Atlassian
“We offer the Atlassian Team Playbook, available free and un-gated, to make it easier for teams to collaborate. It’s full of practical advice, exercises, and templates to help teams discover dependencies, run retros, and define roles and responsibilities.
“We’ve also added some whimsical experiences to the product, like a Halloween-themed animation, or confetti when you move a task to ‘done’. These make the day a little brighter for our users!”
Faus 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
“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.”
“Make sure you have the best, most welcoming representatives at your booth. That means standing outside of the booth sometimes, making it clear to attendees passing by that you want to speak with them. Don’t wait for them to come to you. 85% of consumers are likely to purchase from a brand that creates a positive, memorable experience.
“Make sure your booth‘s messaging is very clear. Not just your company’s name and logo — but what your company can help people with.
“Incorporate play/experiential into your booth. Schedule live talks for attendees to stop by the booth and chat with an expert. Give intentional and meaningful swag. Not everything needs your logo blasted on it.”
Moni Oyolede, Founder of MoMartech
Read: 3 bitter truths all marketers need to hear right now
Oyolede asked, “If you could redesign the way creatives and marketing professionals work, what non-negotiables would you include?”
Cristina Jerome, Founder of Off Worque
“First, I‘d make work/life balance a structural expectation and not a personal responsibility. After working in marketing for ten years, I’ve seen the best output from every team not only when we‘re well rested, but we don’t feel anxious to ask for rest and use our PTO.
“Structurally, I‘d include flexible work blocks, projected no-meeting windows, and half days on Fridays all year round. Additionally, I’d prioritize mental health literacy for managers. If marketing is an always-on industry, we need leaders who know how to recognize burnout, support employees through high-pressure seasons, and model boundaries themselves.”
Read more: Use the ick to create better marketing
