The Art of Storytelling with Terry O’Reilly


This is the first of a two-part interview with Terry O’Reilly, interviewed by Emily Gilbert

Terry O’Reilly always starts with the end in mind. For any great story, he says, a satisfying ending is absolutely critical.

And he should know. A renowned ad man and award-winning commercial director, he’s the author of several books and the host of his own CBC radio show, Under The Influence. To add further to his list of accolades, he even co-founded his own company, Pirate Radio, when he was just 29 years old.

His creativity and entrepreneurial experiences have resulted in countless tales of the advertising industry that are as much entertaining as they are inspiring. Our conversation with Terry covered everything from the digital revolution to the trials and tribulations of starting your own business – but it begin with his story about a group of ad-savvy nuns.

On your website, you mention that you created an ad campaign for a group of nuns. How did that come about?

It all started one day when I got a phone call from a nun. She said the convent was a big fan of the radio show, and that they had a branding problem they wanted to chat with me about.

“We don’t wear our habits any more,” they told me. Nowadays, nuns dress like everyone else – so they had, in effect, lost their branding. They said that if women feel a spiritual calling, they often don’t know where to turn today. The nuns and the convent needed awareness.

They told me that they had struck a deal with the transit company in Sault Ste. Marie, where they were based. The company had given the nuns a huge discount on interior bus advertising, and they wanted a creative approach.

I called the transit company and asked them if they had ever put an ad on the inside ceiling of their buses before. They said they hadn’t. So, we that’s where we put the ad.

The copy said, “If you’re looking for answers, you’re looking in the right direction,” with the logo of the convent, and a link to their website. No one had ever seen an ad on the ceiling of the bus before, but for this client, it was the perfect place. When someone is standing on the bus in the minutiae of their daily commute, and looks up in a period of introspection – that’s the first thing they will see.

The response was incredible. The nuns got press right across the country. The Globe & Mail did a half-page story. The nuns were very happy with the result. It’s proof that it’s not just creativity of the message that matters. It’s also the creativity of the media.

How do you think that’s evolved over the years, the relationship between creative and media?

The digital revolution has played a huge role. There are a lot more channels available to advertisers than ever before, and while you can buy ads on social media, you don’t have to. All you have to do is spend time.

When I worked agency side in the 80’s, media was considered more of an entry-level job. They were isolated, they weren’t really a part of the meetings we had. But now, media are super stars. They have a big seat at the table.

The best agency I worked at was the one that had the most collaboration between the departments. There’s a different kind of camaraderie when everyone works together instead of in silos. The work is infinitely better.

And when you’re getting to work on a new brief, is there any one thing you do to kick start the creative process?

I don’t think I had any real formula for that. But at Pirate, we would start playing some “What If” games.

The culture I tried to create at Pirate, which came from agency life, was a culture where everyone felt safe to stick their hand up with a kooky idea. No judgement. I always wanted to hear everything that was on my writer’s minds.

Why? Because in my career, the biggest ideas came directly from the silliest idea of the day. They were either brilliant ideas in disguise – or at least the stepping-stone to a huge idea.

And at the very least, we’d have a lot of laughs.

Another key thing for me is making sure I understood the brief inside and out. One of my former clients was Nissan, and I was briefed on a campaign for their top-of-the-line, very expensive 7-series sedan, I insisted that I get to drive the car. Clients didn’t like that idea, but I had to know what it was like to drive it. So I got to take it for a test drive. And when I did, I remember noticing these little footstools in the backseat of the car. It was a tiny detail that wasn’t anywhere in the brief, but an unexpected surprise that I was able to weave into my writing.

I always believe that no copywriter should ever write a campaign if they haven’t held the product in their hands. It’s the tiny touch or smallest of details that can make all the difference when telling that product’s story.

What is the defining thing in your mind that makes a story successful?

To be honest, there’s no sure-fire formula. It’s not easy, creating a great story. It takes crafting, structure and wordsmithing.

I tell a lot of stories on my radio show, and to me, a great story is kind of like a great dinner. You have this wonderful, teasing little appetizer, a satisfying main course, and a delicious dessert. That to me is the structure of a great story. It starts with a compelling intro, so you’re intrigued. The meat of the story is revealed in the main course – you’re immersed. And the end is an indulgent dessert that leaves you feeling thoroughly fulfilled.

Endings are the toughest part of storytelling. You’ll often hear people say that they liked a book or a movie, but “didn’t really love the ending.”

As a writer, I would start with the ending. When you know the ending, the middle part is easy. If writing a script, I would always try to figure out how it would end before I would begin to write.

I’ve heard that Stephen King often just starts writing, with no clear plan or end in mind. But novels are an entirely different medium, with no length constraints!

With book writing, you have so much more freedom. You’re not confined to thirty seconds or one page of a magazine. In many ways, a commercial or ad needs more discipline. But interestingly, some famous novelists honed their craft by getting their start in advertising.

Salmon Rushdie once said that the early days working as a copywriter at Ogilvy & Mather really helped him form his craft as a writer. He learned not to waste words. And mega-author James Patterson used to be creative director at JWT. There’s a discipline to being concise that you learn when you’re a copywriter.

And certainly when it comes to advertising, you have to be able to tell your story quickly and grab your audience at the same time. You’ve said yourself that ‘persuasion is an art’. What’s the secret to getting an audience’s attention?

Surprising creativity rooted in insightful strategy. If the strategy contains an insight that is meaningful, the creativity becomes an expression of that. If an ad has great strategic underpinning, it’s a powerful piece of communication. And both elements together position your product against the competition.

What happens to the creative if the strategy is off?

When there’s a weak strategy, there’s probably no persuasion. The strategic element in advertising is everything. We have lot of great creative people. We desperately need strategists.

A commercial without a great strategy is like a beautifully wrapped birthday gift without anything inside. A lot of ads fall into that category.

See, in my view, an ad does one of two things. It attracts a new customer, or it convinces an existing customer to use product more often. The new customer is ground zero. The existing customer already has some loyalty to the brand – but both still require persuasion. Smart marketers are always aware of persuasion. Making an ad is not just an exercise in comedy. There has to be persuasion. There has to be a sale at the end of the day.

How do you implement the strategic side of things into your work now?

It’s interesting, because my whole radio show has evolved into strategy. It’s a distinct evolution for me, because I’m a creative guy. When I revamped the show to become Under The Influence in 2012, I opened it up to marketing, not just advertising. So it’s interesting that the show has completely evolved from a study in creativity to an analysis of strategy. I’ve come to believe that strategy is the key differentiator, more so than creativity.


Thank you to our guest interviewer Emily Gilbert. Emily is freelance writer with a background in advertising and communications. Fuelled by caffeine and curiosity, her love of travel has brought her to all seven continents.

Stay tuned for the second part of this interview where Terry shares his single biggest piece of advice for succeeding in the advertising world.