In the first episode of Message Received, host Jennifer Madigan speaks with Jennifer Stewart, Founder and CEO of Syntax, about how communications has evolved over the past decade and what that shift demands of leaders today. They explore the move from traditional media to fragmented digital channels, why communications must be treated as a C-suite function, and how over-caution, over-approval, and the pursuit of perfection can slow progress and weaken impact. Stewart shares practical insights on originality, leadership visibility, and why momentum and clarity matter more than flawless execution. The conversation ultimately makes the case that in today’s environment, playing it safe often carries more risk than moving with intention and that credibility is built by showing up, not waiting.
Jennifer Madigan.
MESSAGE RECEIVED — EPISODE 1 TRANSCRIPT (WITH TIMESTAMPS)
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Hello and welcome to
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Message Received, a podcast by Syntax. I’m Jennifer Madigan.
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On this show we talk about how messages actually land, how strategy, storytelling and audience
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insight comes together, and why some ideas cut through while others don’t.
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Each episode, I’ll sit down with people who shape narratives for a living.
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Leaders, builders and communicators who understand
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what you say and how you say it really matters.
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Let’s get into it.
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Today I’m joined by Jennifer Stewart, founder and CEO of Syntax Strategic.
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Jen’s a strategist, a builder, and one of those leaders who really understands
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how messages land not just inside organizations, but out in the world.
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She’s also a strong public voice.
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People know her in Ottawa and far beyond.
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And that didn’t happen by accident.
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Jen, happy to have you here.
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This is exciting getting this new podcast up and running.
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This is so fun.
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I’m so glad we’re doing this.
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And for those that don’t know, Jenny and I have worked together now for nine years,
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so this just feels like another one of our many conversations that we have during the day.
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So I’m excited.
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Yeah, it’s so funny you posted the other day about, you know, I really first met
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you just to pick your brain on what is this world of communications, public relations?
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I had no idea. And I walked out with a job offer,
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which is
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I’ve told people I have put out official
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job postings, rather,
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but I’ve actually never hired somebody from a job posting.
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It’s always been a gut.
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I remember you walked in there, you had little Griffin in tow, so he would have been about like six or seven months.
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And you just had such creativity.
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And you really, it’s rare for a journalist
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to understand the news side of the media,
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but then to be able to at least even have the curiosity
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in terms of how does that translate strategically to, you know, what many call
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the dark side, but the world of public relations and public affairs and strategic communications.
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So, I would say that was one of the,
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if not the best professional decisions, that I made.
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And there we are nine years later. Yeah. It’s incredible.
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I have to say, I remember I had started doing a little bit of work with a diaper company, if you remember.
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Yeah. Yes.
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To try to learn this side of things.
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And then obviously I did with you and.
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Yeah.
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Yeah, completely different turn in my career, but one that I, I’m really happy that I made.
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So Syntax has been around for 15 years.
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And I’m wondering how has that communication shifted over that time?
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I think it’s shifted significantly.
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You know, when I started in the agency world, which was, you know, nearly 20 years ago, right.
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Syntax has existed for 15.
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And I had a few years of experience before I started the company.
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It was really like you.
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You were watching the news.
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There were official channels to disseminate information to people, and it’s like the 6 p.m.
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and the 11 p.m. news.
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Those were your gospels.
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And if you got a client on the news, you were reaching your audience.
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For the most part. And we have seen things drastically change.
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You know, when we started Syntax, I didn’t have social media, and I’m a communicator.
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Like, it was just coming on the scene.
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And you see the shift where people get information so instantly from their phone
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and you can’t pinpoint exactly where they’re going to be getting that information.
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You need to understand their psyche,
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their interests, what they’re looking for in terms of their feed, and then try to unpack that algorithm
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so you understand their echo chamber and then crosswalk that with audience segmentation,
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because communications is not throwing something on the wall and hoping it sticks
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is how do you target your audience
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so that your message lands with your desired, your desired end state.
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So it’s really shifted.
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It’s become a lot more complex.
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It’s become a lot more nimble and a lot more agile.
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But it’s also, I think, become a lot more fun because now it’s just hyper, hyper strategic.
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So you get to be creative, you think outside of the box and you always have to be thinking about, you know,
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how am I staying on top of these trends while also mirroring what is the the weight?
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And, you know, the consistency of my message with the trends.
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Because at the end of the day, what hasn’t changed is the strength of a message.
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And there still needs to be, you know, frankly, as solid as ever before.
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So what do you think?
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Most organizations are getting right and wrong these days?
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I think a lot of organizations are understanding
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the need to communicate, and that it’s not just a
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nice to have, but communicating well
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and effectively and frankly, creatively.
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And breaking through the noise.
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Not to talk in cliches is essential to your brand,
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which is essential to making money and driving revenue and staying in the game.
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So I think people are finally correlating the fact that communications
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needs to be treated as a C-suite function, and it’s highly strategic.
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And if it’s not strategic, you’re selling yourself short.
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I think that a lot of
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organizations are still imitating and playing it safe.
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My goal for 26, I want a highly creative, unsafe campaign for an organization
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that’s going to hit the mark, right, and make them stand out.
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Like, I think a lot of organizations see a campaign.
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You know what lands, it’s safe.
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I’m still a little punchy.
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So they emulate it versus, you know, frankly, having the corporate guts.
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And I understand why it’s difficult, the corporate guts to think outside the box and try something new
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and to stand apart from the crowd.
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And as it gets busier and online becomes even more prevalent,
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which is crazy to think that it can be even more prevalent than it is today.
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People are going to have to be really, really creative without being crass and without being attention seeking.
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But they need to be innovative and they need to be a mode of yeah, I think of a lot of times
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when people ask, you know, should we go on TikTok for instance?
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Right, right.
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And it’s like, that’s not a space where you can go and do the same thing.
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You’re doing everything else, or play it really safe. Right.
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The exact accounts you see on TikTok are doing TikTok,
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and they’re throwing a bit of that caution to the wind.
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And really, they’re leaning into the trend, they’re creating the trends.
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Exactly.
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And I think, too, I read this article about Instagram and TikTok, where, you know, a
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trend starts or there’s, you know, a trending audio,
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and then everybody jumps on the bandwagon and,
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you know, essentially copies that original reel or that original TikTok.
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You know, I don’t think that is going to be the case in 26.
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I think it’s going to be original content. Original content.
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The original content is you’re actually going to break through the noise, and that’s going to create a bit of a race
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in terms of, you know, pushing boundaries and what people are willing to put on the internet.
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And mixing the, the kind of
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sometimes needed corporate caution in terms of reputation and brand with,
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you know, pushing the boundary and pushing the edge and having strategic communicators
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where they can not be risk averse but advise you like,
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how do we push this in a way that still aligns with your brand without being shocking
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for the sake of being shocking but still getting attention?
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It’s going to take a lot of thought.
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And these things look so like knee jerk,
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but they’re not. The ones that are done well, often are thought out and strategized.
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Second guess, what advice would you give to leaders who, you know, want to do this?
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But it does require allowing some leeway
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in the language or in the things that you want to do.
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So how do you set a boundary, that you can have a bit of that,
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brand safety maybe, but allow people to be really creative and do that unique content.
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I think you just need to understand that
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in today’s era, you need to let go of kind of this sense of control.
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You know, me, Jen.
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I’m a recovered control micromanager. Right.
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You need to understand that to stay in the game and to play in the game, that you need to take some risks.
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And they can be really intentional, calculated risks, but you can’t play it
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safe, and brands can’t play it safe and continue to evolve and continue to have a presence.
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I mean, you know, this was a matter of technology,
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but if you look at the Blockbusters and the others, like brands will die as technology evolves and you have to stay relevant,
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you have to evolve your service offering, which in turn, you know, evolves your communication.
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And you need to be thinking about your business as a whole, not just how you communicate as a whole.
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In the world of AI.
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Like, is my product going to be relevant in five years?
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If it’s not, I don’t want this business to sink.
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The best businesses iterate and change.
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You know, I worked with gasoline retailers for many years,
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so I’ve got the utmost respect for them because they’re business people, and they were always looking at, okay,
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what do I need to bring in from a convenience side, if people are buying less gas, do I integrate EV charging stations?
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Do I integrate restaurants like the best?
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Businesses aren’t going to die with the change in technology.
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They’re going to adapt and they’re going to pivot.
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And that’s what I think businesses need to do.
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So it’s not just how you communicate, it’s what’s our core service offering.
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What are we communicating?
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Is it sustainable?
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And if it’s not sustainable, how do we iterate so the audience can adapt to it.
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And then how do we communicate that iteration.
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Yeah. So we’re talking about brands.
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But you personally are very strong,
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online, you know, in media and on social media with your own personal brand.
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Why has that been important for you?
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So it’s really funny because I think you will get this because,
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you know me, I’m actually an introvert.
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I can turn it on.
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I’m not socially anxious, but it doesn’t fill my cup.
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And if you actually know me, you know that to be true.
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I made a conscious decision that at 29, when Syntax was still in its infancy, I think it was just communications at the time,
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that I remember I was waiting to go live on TV
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and it just clicked that, you know, this isn’t about you.
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This isn’t about, you know, the Jen Stewart Show.
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This is a means, by profile, whether that’s television or social.
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It’s a means to drive awareness, a means to drive credibility, to drive brand.
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And in turn, that’s revenue.
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So it sounds really crass to say, but I’m going to own it.
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I have an online presence that’s authentic and genuine, because I want to build
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a brand for my company, for my team members, and it builds credibility and trust.
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And I’m practicing what I tell my clients to practice, which is put yourself out there
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with authority, credibility and confidence and do it often.
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And don’t second guess everything.
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Not every post needs to go through ten layers of approval.
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Not every word needs to be nuanced,
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and the more you do it, the more comfortable you make doing it.
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I’m going to say a lot of leaders are anxious, though, right?
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We do have a lot of clients that recognize the importance of this, but come to us and say, you know, how do I do it?
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Help me, you know, so what do you think that fear is about?
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First of all, I think there’s a lot of insecurity
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about how you’re perceived, and I’ve had to compartmentalize that.
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As long as, you know, the content is somewhat either really authentically me or,
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you know, very serving in terms of the ideas and the recommendations for my industry,
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you have to stop caring about people liking you
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and understand that the 30,000 ft perspective is brand awareness.
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Awareness for your organization, awareness for your expertise.
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And essentially, at the end of the day, a funnel to drive clients because they know who you are and you’ve become a trusted voice.
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You know, I always say to my kids, when you learn a new word, it feels like you hear it ten times in the same week.
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And they’re like, how have I never heard this word before?
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It’s kind of the same thing about an online presence.
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You can’t just do it once.
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You’ve got to reinforce it and reinforce it,
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and then it just seems like a norm.
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It seems like a comfort and a trusted space.
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So stop caring what people think.
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You’re going to mess up sometimes.
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And again, no one really thinks about you that much anyways,
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so they’re not sitting thinking
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about Jennifer Madigan’s post from a week ago,
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and so it was perfect.
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And just put yourself out there.
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Yeah.
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What would you say to leaders, though, who feel like they don’t know what they have to say when they go on social media?
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I don’t know.
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This would be a sales pitch for genuinely hire a firm, hire a firm.
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But it’s true.
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I don’t mean that in a salesy way.
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Hire a firm who exemplifies that type of vision, which is frankly why I do it.
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And I encourage the whole team to do it.
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Because if you can demonstrate that you can do this in a way that’s nuanced,
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so personal, so authentic, but it’s also credible, then you can do that for other people.
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And a really strong communicator can navigate different sectors.
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So I always say, you know, people ask what does Syntax specialize in?
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We kind of specialize in everything.
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So we don’t need to be the experts in an industry.
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We need to be where expertise marries industry knowledge,
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because we’ve got former journalists and political staffers, they know how to cut through the noise.
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So I would say hire somebody that’s
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actually going to take the time and has the expertise to understand your voice
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and not just have, you know, ChatGPT generated posts.
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And I find too, if you can at least have someone get you started or give you a couple of things,
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the good thing is that habit of just going online and hitting post.
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Suddenly your brain starts to look for things in that vein as well.
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Like, oh, I could also do this while I’m here,
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or I could repost that.
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And so I always say to our clients too, let’s aim
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for something small at the start, one to four posts a month,
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and you’re going to find that the more you get there and you just hit that button that you’re afraid to hit,
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the easier it gets, and then it just becomes habit.
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I think that’s it.
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I think it’s to also, you know, trust your gut.
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You know, I’ll post, you know, at least one or two times a day.
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And I’m probably spending no more than 20 minutes on it a day. Right.
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But that’s evolved with time. It’s a muscle.
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It’s a continued sense of confidence.
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And this is where I need to slow down. Sometimes it’s not overthinking.
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You know, I did a series on LinkedIn of men who’ve been supportive of my career.
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I’ve had a ton of male mentors, and I’ve been really fortunate to have a ton of male mentors.
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And I think I thought about that’s a great idea for about a second,
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wrote my first one and had it up in two minutes.
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And it’s not to pat myself on the back and be like, oh wow, you’re so fast.
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It’s just I knew it was a good idea,
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and I knew that I wanted to recognize these individuals,
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and I knew also it’s important to the conversation that women aren’t here and men are here.
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And I didn’t overthink it.
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Whereas I’ve seen in some organizations, and this is where I do think,
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to answer your question from a few questions back, what are some mistakes?
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They overthink it.
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They take it to the board table, you know, think about it for a month,
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and then it also gets written in the plan and then it won’t get done.
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You just have to move.
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And that’s my biggest piece of advice.
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With how fast the world goes right now,
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you need to have somebody that has a really good strategic gut
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and you just need to move because it’s way better to,
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you know, die from movement than it is from sitting still.
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Yeah, absolutely.
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I love that.
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So this has been a big year for Syntax already.
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First of all it was the 50th anniversary.
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Opened the Vancouver office.
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So a lot of things have happened this year.
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But I want to also look ahead to next year because 2025 is almost done.
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I don’t know how time goes as quickly as it does,
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but what are you looking forward
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to most as we head into 2026?
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I really feel like 2026 is going to be a year of growth.
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You know, I did post about this
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and I didn’t intend to talk about this,
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but I think it’s actually really important to understand our mindset.
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We were approached by two companies in the last year or two to be sold,
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and I went through the process because it was an interesting process.
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I learned a lot.
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But I made a very conscious decision that, like, we’re just getting started.
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You know, I think we’re pretty successful in the communication space,
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but why can’t we be even bigger and do even more impactful things?
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So I really want 2026 to be a stretch year
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for our team in terms of the work we do, the quality of the work, and frankly,
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you know, the size of the work in terms of the audience it reaches.
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And I think there’s a lot of opportunity in the defence space,
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and certainly, Jennifer, I know that’s something that you have expertise
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and we’re bringing in two incredible associates,
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one by the name of Adam Thompson, who was in the military himself
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and worked as a communications officer in the military.
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And then former Senator Vern White,
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who was also the chief of police for the Ottawa Police Service.
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So I think, you know, we’re really going to bolster that team.
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And you were also an embedded reporter
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in Afghanistan and bring that defence expertise as well.
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Yeah, it’s true.
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Obviously, one of the most exciting things I did in my career included covering the military.
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I remember when I was first a videographer in London, Ontario,
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and the assignment editor there saying, be very careful about where you take your next job.
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Think about, you know, even if you’re going to be in a small office somewhere
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when you’re starting as a reporter, pick an office where it’s a national interest.
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And so I took a job in Pembroke, and I covered
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the military up there, and it led me to follow a platoon for a full year.
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And then I got to go over to Afghanistan as an embedded reporter
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So yeah, I’m looking forward to this work as well.
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I think the fact that you, as a reporter,
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have been able to tell the story of Canada’s military through the lens of a journalist is incredibly important.
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And that’s exactly what I want to do.
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I want to tell the stories of our military and of our defence sector and also help,
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when it comes to communicating any types of change management or recruitment.
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And I think there’s a lot of potential there.
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Yeah, there’s a lot going on for sure.
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All right.
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Well, thank you so much, Jen, for being here and being part of the first podcast.
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And I’m really excited to keep this moving and talking to some really interesting voices over the next set.
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Yeah. Thanks for having me. I think it’s going to be great.
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We’ll do a recap in a year from now and talk about all the exciting things we did.
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Let’s do it.
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That’s it for today’s episode of Message Received.
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If you enjoyed listening, follow or subscribe wherever you listen to podcasts,
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and you can find more from Syntax Strategic on LinkedIn and at Syntax Strategic Dossier.
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Jennifer Madigan.