Second City’s Andy Eninger On What Separates The Content Greats From The Jesters

Published: December 13, 2016

Much like aspiring comedians have to stand out among the competition in order to catch their big break, marketers have to make sure their content trumps others’ for clicks and engagement. With a sea of content out there in the B2B marketing space, buyers have no shortage of information to help them make their decisions. That’s all the more reason to not just create batch-and-blast content, but instead give current and potential customers a unique story to remember.

This was the key topic discussed during our YouTube Live session with Andy Eninger, Lead Designer, Facilitator and Head of the Writing Program at The Second City. For those of you who may not know Second City, you’re sure to know the talent that has sprung from the premiere comedy theatre and school of improvisation. Famous comedians and actors such as Tina Fey, Steve Carrell and Bill Murray have all started their careers at Second City.

Second City has a division, called Second City Works, to help corporations generate content and discover insights on connecting with customers, other companies and clients. Eninger will be taking his knowledge of the space to the big stage next February at the Content2Conversion Conference — now a part of the B2B Marketing Exchange — on behalf of Second City Works for a keynote session called “Collaborating With Your Customers To Create B2B Messaging That’s Not 2Boring2Care.”

This week, Eninger sat down with Alicia Esposito, Content Strategist at Demand Gen Report’s parent, G3 Communications, to learn more about what separates the content marketing greats from the jesters.

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Discover Appropriate Humor With Trial And Error

Eninger said companies come to Second City Works for the comedy, but humor isn’t always right for everything. Companies have to adhere to a style and tone, and humor carries both risk and opportunities, he added. Those risks are what tend to make people hesitant about using humor in their work.

“You can have all the book learning and technical skills in the world, but you don’t know what the connection is going to be between two comedians until they start working together,” said Eninger. “For brands, you’re not going to know what’s acceptable to your client until you start putting some things out there.”

Eninger recommends bringing some of your clients into a room to talk through some ideas and see what resonates with them and “where their eyes light up.” You also have to work through a few “misses” to really discover that territory. He referred to this ideation phase as “low stakes.” if you put something out there and it fails, seeing the audience’s (or client’s) reaction can help put the pieces together.

“I think we end up with a lot of high stakes by trying something out and it fails and misses,” Eninger said. At Second City, those misses are such a huge piece of [getting to] know the guardrails. We will know what doesn’t work. That’s as important for us as the things that do work.” 

The Principles Of Great Storytelling

Storytelling is a significant aspect of great content. It’s no longer about delivering the content as a whole, packaged piece,” Eninger said. “It’s about letting the person complete the story.”

He explained: “I think really engaging content marketing is the kind where the person on other side is able to complete the story, or there’s a piece that requires their engagement.”

That content is built gradually, with input and interaction from the audience. “For us on stage, we have the audience shout things out for our sketch. That keeps the audience listening. Don’t deliver the whole thing as a packaged piece; give a portion so the audience can build on it. We always say, ‘Bring a brick, not a cathedral.’ How do you find that brick that people can build upon?”

Eninger advised steering away from simply proving your own point of view. Instead, consider a “hero” when you have an idea. “We have a tendency to share things from our point of view. [You should] be able to talk about the experience with your customers as the hero.”


Want more? Check out the full conversation on YouTube here, and don’t miss Second City Works at #B2BMX this coming February. 

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