Shannon Gallagher on Truth & Strategy

Shannon Gallagher is a brand strategist & writer based in the Hudson Valley.

I start all these conversations with the same question, which you know, of course. I borrowed it from a friend of mine because it’s such a big, beautiful question—but because it’s big, I tend to over-explain it, like I’m doing now. Before I ask it, I want you to know that you’re in total control. You can answer or not answer any way you want to, and it’s impossible to make a mistake. And the question is: Where do you come from?

Even knowing this is coming, there’s really no way to be prepared. Where do I come from? I come from here. I live in Red Hook.

I was born in Hudson, just up the river. I grew up in Tivoli, right in between. I’ve been here for most of my life and definitely feel very of this place. I imagine that happens when you spend so long in the same geographic area. This is where I’m from.

What does it feel like to be of this place? What does it mean to be from Tivoli?

There’s such a long tail of experience, and it’s changed so much. Now in my 40s, I see how much has shifted in the last five years, and even more in the decades before. So much of my life has happened here. It’s tied to this place.

My family is from here too. In a small town, that means something. You and I have had this experience: you run into someone on the sidewalk and they say, “Oh yeah, I know your mom, I went to high school with her.” It feels like we live in generational stories. My family’s story is here too.

What was it like growing up here?

It was great. Tivoli, which is well known now, was very different. My dad talked about how you couldn’t even get a loan from the bank to live there. There was a motorcycle gang safe house, drugs were dealt there. If you lived in Tivoli, you were probably an artist or some other unsavory character.

My parents bought their first house there for $25,000. It was small, on a dead-end road, and everybody knew everybody. You were a Tivoli kid. My older brother says we were the hippie white trash—which feels accurate.

We were bused to school in Red Hook, where most kids lived in developments and their parents worked for IBM. If you came from Tivoli, you were different.

It’s still very much that way. I lived there for quite some time when my daughter was young and raised her there for years. A lot was the same—the kids had free run of the place, even at a young age. It was safe, intimate. But now it’s definitely fancier.

Do you have a recollection—I'm dying to hear this—what did young Shannon want to be when she grew up?

Oh boy. I think it changed a lot. Still does.

I remember going through a phase where I wanted to be a doctor. A phase where I wanted to be a marine biologist—I think most kids go through that phase. I went through a phase of wanting to be a designer, a fashion designer.

But the most pervasive one, I think, was being a writer. I always kind of came back to that.

What did that mean to you, do you think? What was a writer to young Shannon?

Oh, I mean, I loved books. I read very early, and they were a real refuge for me growing up. My grandmother, who I was extremely close with, was a remedial reading teacher in Hudson.

So much of my childhood—so many moments of feeling connected, or inspired, or safe—really came from being read to or reading. Even at a young age, I used to drive my older brother nuts. My mom likes to tell this story, because I would be so excited about what I was reading—about the idea that a story could not just take you somewhere else, but really make you feel things.

I would get so excited about that. I’d want to share what I was feeling. I’d be like, “And then this happened, and then this happened, and then they said this…” and my older brother would get so annoyed. He’d say, “Enough, Shannon.”

But I just so badly wanted him to have the same experience I was having. So yeah, I think I was really enchanted by the power of language and storytelling at a very young age.

And to catch us up—what are you doing now? What are you up to? What’s your work?

What’s my work? Well, my work is evolving, let’s say that.

I got a degree in literature and creative writing. I did some postgraduate work in literary nonfiction at the Salt Institute for Documentary Studies in Maine. I intended to be a long-form journalist. I wanted to write for magazines.

Life had slightly other plans. I ended up—through someone I met… You know, if you live in the Hudson Valley, especially before COVID and remote work—if you worked here, you did a lot of different things. It wasn’t like now, where we have such a big creative community because people can work on Zoom or have hybrid schedules.

I freelanced for a couple of publications. I taught Pilates. I bartended. It was a real mixed bag.

Through someone I met teaching Pilates—who then joined a writer’s group I had—I got my first copywriting job. She had an agency. I didn’t even know that was a career.

That’s what brought me into the world of branding and advertising. I worked as a copywriter doing comms, and then got into strategy. For the last six years or so, that’s been my job—working at an agency, copywriting, brand strategy.

I was recently the head of strategy at a B2B agency in the city, and left that job in mid-June to work with you.

That’s right. Congratulations on both counts. I always congratulate people on departures and transformations—good or bad, all big changes deserve it. Congratulations on that. And of course, this is the official announcement of Gallagher Spear. What do you love about your work? Where’s the joy in it for you?

Oh man. Where is the joy in it for me? You and I have talked a lot about this.

The joy is in the work itself. Talking about the work—great. But it’s doing the work. It’s having a problem to solve. Figuring out what that problem is. Figuring out what questions to ask. All of the research. Gathering all of the information. Talking about it. Hashing it out, like we do—even when we fight.

Absolutely.

And starting to make sense of things in a way that—yeah, in a way that makes sense. And then translating that into work that makes sense to other people, and that people can do things with. That whole process—I just find it so fun and exhilarating. Sort of the discovery, the act of discovery.

Yeah. I'm curious—I really identified with the way you described that. I don't know if I'd heard that story before, that you were doing all these different jobs in Red Hook and Tivoli and then sort of got plucked—or invited—into this world. I identified with that. I mean, I wrote a very arrogant cover letter to a brand consultancy in San Francisco—that was my beginning. And I didn’t really know. I had no idea what I was doing or what I was applying for, really. But I feel like I found a mentor there—this guy, Mark. So I’m curious: can you tell me more about that story? About being pulled into the industry as a copywriter? What that was like, and that relationship?

Oh yeah. It was Alicia Johnson, who you’ve now met—Johnson & Wolverton. She had a boutique branding and creative agency. It was complete happenstance that I met her. She went to the Pilates studio in Hudson where I taught. Her teacher was out of town, and I was covering for her.

Alicia and I just instantly hit it off and stayed in contact. She had been working on a book, and I had started a writer’s group—just because I was feeling, you know, I had a toddler, I was a single mom, I was doing all these various jobs, but really starving for creative connection and an outlet.

So I started this writer’s group. She came, and I ended up editing her book. It was in that relationship—and I guess you'd have to ask her what it was she saw in me—but yeah, it was a project for Food Network. And I just remember being a little gobsmacked, like, I get to play with words? Come up with ideas? The assignment seemed so fun.

She still remains my mentor to this day. And she has this gift—I’ve seen it with her and other creatives—she knows exactly what to ask of you, exactly how to give you the assignment in a way that gets all your synapses firing. She teaches you to get comfortable with the idea that you can’t get it wrong.

She kept seeing things in me and kind of threw me in the deep end—so I could see what I was capable of. I loved collaborating with her. I loved working with the other creatives. It was this idea that we were taking human insights and cultural insights and translating them into—objects, if you will.

That whole process was just... yeah, it was fun. Just like when you and I work together—it’s so fun. And I think that’s where the best work comes from—that chemistry. Between the makers, but also with clients.

Yeah. I’m really connecting two things you said. One—well, I guess it was an idea that came to me as you were describing something earlier, about words. You talked about playing with words, and how much of this work is that—just diving into language, moving around in it, seeing what happens, paying attention. So much of it is about words.

Mm-hmm.

It’s an odd observation, but it’s viscerally true.

Yeah. When we used to joke about doing this together, and then we actually started working together—we were on a project, and the client, in one of the early meetings, said they wanted to do some qualitative research. And they said, “We want to be saying things that no one else is saying.”

You and I had that conversation—well, if you want to say things no one else is saying, you have to know things no one else knows. And that starts with asking the right questions.

And you always say—and I’ve told you this before—I love what you say about how research starts at the invitation. The words really do matter. From the questions you ask to get the information, to the way you then communicate those ideas back to the client so that they really understand. It’s so much about communication and relationship.

And then, of course, the final product—saying things that make people think, feel, and do what you want them to do, or what will serve your objectives.

That relationship piece—and the clarity of communication—is so important. And it gets lost, right? It gets lost a little in the traditional agency structure. Or maybe not lost, but deprioritized. Stymied.

Can you say more? What are you pointing at? What have you learned about how to make that kind of work in an agency structure?

Well, I think it can be really challenging, right? Because you're doing a lot of stuff not because it serves what you’re trying to achieve, but because it’s what needs to get done.

We’re at a moment—so many people are talking about this—where the agency landscape is changing. There’s this essentialism happening. Clients don’t want big, bloated processes. They have a problem to solve, and they need to solve it. It needs to be effective. It needs to happen quickly and efficiently. There’s not a lot of time for the rest.

So, as I said, chemistry really matters. When you have, in my experience—and I think most people in this industry would agree—when you have a strong rapport with the client, when they trust you, when they feel heard, when you understand what they’re trying to do, the work turns out so well. And it’s usually really effective.

It becomes a very co-creative process. And you also get to be trusted to be the expert. That’s so much better than when it’s transactional—agency as vendor. A lot of assumptions about what the problem is. A default to recycled, surface-level insights. Everyone kind of doing the same things.

That’s part of what excited us about Gallagher Spear. Working the way we want to—just you and me and a client—you get to have that intimacy. I hesitate to use the word collaborative because it’s overused, but it’s really about...

It’s not about having a set process. I mean, obviously there are steps. But it’s more about having an opportunity. An opportunity to learn something. To make something. To do something. Again—to play.

Yeah. The word that came to me before you said “opportunity” was relationship. That’s what I’ve observed in working with you. You listen unbelievably well to the client, and you build that rapport almost naturally. It makes the work better. And selfishly—it creates a better environment for me.

You know, as a researcher, out there talking to people and trying to translate that back into the organization—I don’t always have a safe space. And I’m not always good at that. But you’ve always really understood what I was trying to say. I don’t know if that’s an asset or what, but it’s made our collaboration really fun.

That’s how I came up, really. I was told at the beginning to just follow my curiosity—that was the only thing I needed to listen to. And that means sometimes saying things that don’t always make sense to people. I’ve had to learn to be a better communicator. Which is a long-winded way of saying that the bridge you and I provide is really powerful. And we don’t see that much anymore.

The last thought in this pile of thoughts coming out of my mouth is this: for so long, as an independent—because I’ve been independent a long time—hearing you talk about agency structure can feel like an alien world. But for a long time, I wanted to appear to be a company. Do you know what I mean? Like, over the last 15, 20 years, the last thing you wanted to be was some jackass out on your own. You wanted to look like a company.

But now, on a meaningful level, that’s not the case anymore. You want to appear to be a human being. A person someone can have a relationship with. So you can—like you said—get into that playful space, get creative. That seems to be what people are really hungering for.

Yeah. That idea—I can’t remember where I read this—but as we turn more toward things like AI, the thing that becomes scarce is connection. Intimacy. Human-to-human interaction. So being able to offer that has real value.

I love that both clients and creatives—designers, account directors—we’ve worked with, when we told them we were doing this, they said, “I want to come work with you.” They enjoy it as much as we do. And I think that says something.

You’re right—once upon a time, you couldn’t say, “Well, we’re a lot of fun to work with.” But now, it works. Or at least, we hope it does.

Yeah, we hope it does. Yes. So, I’m curious—two things I always circle around. I’m always curious: when did you first encounter the idea of brand? The concept of brand? And then also qualitative research—those are two big buckets for me. So let’s start with brand. When did you first encounter it?

Oh, geez. Honestly, I think it was when I started working with Alicia. It was never something I had thought about before. But also, I think brand has really changed—what it is has changed.

That was when I really started to understand it as kind of a living, breathing thing. And over the years, it feels like it’s become more malleable. Things change so much faster. Brands need to be everywhere and able to adapt much more quickly than even ten years ago.

And that, if I may segue to the qualitative piece—that’s why it’s so important to base your brand work and communications on a real understanding of what’s happening in culture, and with the people you’re trying to connect with.

So much of the packaged process—the agency promises we’re trying to get out from under—they perpetuate the idea that we know something, without actually knowing anything. We make assumptions based on what other people are assuming. But when you sit down and talk with people, and listen—and I’ve said this before, but it’s 100% your superpower—you hear things. You learn something.

That somehow gets skipped over. We see it all the time. Clients just want to skip the research. “Can’t we just go straight into brand development?” It’s such a missed opportunity.

My first exposure—not necessarily to qualitative, but to ethnography—was at school, at SALT. We studied fieldwork, ethics of fieldwork. We spent three months out in the field, working on a story. That’s where I learned about observing, watching, listening—letting stories reveal themselves.

And I feel a kind of relief now, in what we’re doing. One thing that was always a bit of a tough fit for me in agency life, especially in strategy—there are a lot of big personalities. People talk a lot, talk fast. It’s very extroverted.

I’ve always been quieter. I listen more than I speak. And I’ve gotten feedback in my career that that’s a weakness. But I actually think it’s part of what makes me good at my job.

Yeah, 100%. I mean, I feel like, more than ever before, I'm finding myself really articulate—maybe just because I'm old and thinking about this too much—about really championing the value of qualitative, and what it does.

You know what I mean? I don't think we're always told—unless you go to school and study this stuff—I don't think the business world tells you, "Hey, you know what? You can get all that quantitative data, and that's great, but there's also this other form of data that gives you a totally different, but absolutely necessary and complementary kind of understanding."

It’s the kind of understanding that’s going to make you feel so much better about the decisions you make—and probably allow you to make better decisions—because you’re going to consider things you wouldn’t have considered before.

It’s everything you talked about. I think about intuition. This is how I think about it: quantitative is the science of measurement. It gathers big data and gives you an analytical understanding of what’s happening. But qualitative is the science of description. It produces thick data, using that Geertz definition, and gives you an intuitive understanding of what’s happening—why people are doing what they’re doing.

And putting intuition at the center of everything—especially in this moment where, like you said, we’re entering this synthetic madness with AI, where we’re so removed from everything—I think that’s actually kind of exciting.

Yeah, well, especially too when you're talking to—especially in B2B—where there’s not as much understanding of what brand actually is and how it works. Definitely a gap, in my experience, between B2C and B2B clients.

This idea that brand is essentially emotional, right? It’s intangible. It’s a perception. It’s how you make people feel. Yes, it’s communicated through tangible things, but the brand itself is a feeling. So qualitative is critical to that understanding.

And I also think it sets brands up for success—especially because of the demand to be adaptable. Quant is a snapshot. It gives you a view of a moment in time—very useful for understanding a situation at scale in that moment—but it doesn’t necessarily tell you where things are going.

That’s why I’ve always been amazed by forecasters—people who can see around corners culturally. But that ability is based on what you’re saying: watching, listening, intuition. Making space for that—that’s everything.

I feel like I’m being a little indulgent here, talking—but teams are making decisions using an analytical understanding from their big data. But they’re also already making decisions with an intuitive understanding that’s probably not being nurtured or informed.

If you’re not working in an organization that has a qualitative practice, then you're still making intuitive decisions—you just don’t know it. You haven’t gone out of your way to inform your intuition through qualitative research.

So there’s this kind of blindness, honestly, where quant feels like the “right” thing because it’s correct, it’s mathematical, it’s the lingua franca. It’s numerical. All that. And somehow, it makes you feel like you’re standing on an island of certainty because you're dealing with numbers.

But you forget that you’re a human being who’s making all sorts of emotional and imaginative interpretations of what you’re looking at. It’s unbelievable.

Now I’m ranting, but it also occurred to me—there’s a difference between an organization understanding the emotion that a brand or category represents, and its decision-makers actually feeling that emotion.

You can know the feeling—or you can feel the feeling.

And that’s something I’ve enjoyed with you, especially in B2B: using imaginative exercises in a B2B context, and blowing people’s minds with the power of imagination. Helping them unlock the emotional experience of the customer—which isn’t always allowed. Does that feel like a fair description?

No, 100%. That’s the thing. And I’ve said this many times, but people—like leadership clients in the B2B world—they’re people. They have imaginations and emotions. We all work more or less the same.

But it’s such a human impulse—certainty. We want to feel certain. You're making big, expensive decisions. You want to say, “This is going to work,” or, “This is the right thing.” And numbers give that false sense of certainty.

But I’d argue—and I think you’d agree—that having a deep, human understanding of the people you’re serving and trying to reach is a much more stable and secure position.

Even in personal relationships, right? Understanding the person you’re in relationship with allows you to navigate all kinds of experiences—good, bad, neutral. You don’t always need to know the right thing to do or say. You just need to be able to show up, be present, and deal with what’s in front of you.

So it creates more presence, I think—for a brand and for an organization. It allows them to be in dialogue with the people they’re serving.

And like we said earlier, that’s paramount right now. People are super distrusting of brands and institutions.

I remember doing a presentation earlier this year for a client’s marketing summit. They wanted to talk about the “state of brand.” And I talked about how Gen Z is super distrusting of brands. They’re like, “Forget all your super polished, cohesive, coordinated communications. We want authenticity. We want to know your people. Who are your leaders? Who works there?”

They want it to be messy. They want it to feel real.

So there’s this diminishing trust in brand, while also brands still need to be sewn up—organized around an idea. There needs to be a thread. Some consistency.

It’s about balancing those two things. Trusting your audience—and also trusting your people. Helping them develop their intuition. Helping them assess their intuition.

Beautiful.

Well, listen, we’re near the end of our time. What are you most excited about when it comes to Gallagher Spear?

What am I most excited about? All of it.

The kit and the caboodle?

Yes. I’m excited about doing the work with my best friend. I’m excited about doing the work in a way where it can be about the work. And doing it with someone where there’s shared values. I think that’s really it.

Yeah. What are you most excited about?

Oh, yeah. I mean—working with you. Having fun doing work with my best friend. Enjoying the hell out of it.

I’ve been a solo operator for a really long time. So finding someone to collaborate with—and translate the stuff I enjoy into stuff that’s useful for clients—that’s huge. It’s always been a hand-off process for me. So I’m excited to have more contact with the final product.

And what occurred to me was truth. You know what I mean? I think you and I share this—and maybe it’s the journalism part of you—but I’m just fascinated by people. No matter the category, I’m dying to know: what’s the truth of the situation?

Trying to uncover it. Discover it. Articulate it. And then, with your ability to build relationships, to write and communicate—just excited about all of that. About doing good work. Real understanding of what’s going on.

Yeah. And I think too, as we’ve talked about—staying in that space where, you know, especially in my last role, I had a pretty large remit. I was overseeing brand strategy, brand communications, and culture—employer branding. It was broad.

But my favorite part is always the research. Translating that research into big ideas. Outlining the implications. Figuring out what to do with them.

That’s the sweet spot for both of us. And getting to stay in that space—it’s still fairly broad—but getting to go deep is what delights my cat-like brain.

Beautiful. Well, thank you so much for accepting my invitation. I know this was not something you were excited to do, so I appreciate you being vulnerable and joining me here to launch Gallagher Spear.

Yeah, thank you.

And to everybody listening—you’ll find the link. Come say hello if you have a big problem that needs solving.

All right. Bye, buddy.

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