In Conversation: Steve Kakos

Steve Kakos is the Vice-President of Second City Works, the B2B side of the famous improvisational theatre company. Pulling from the heritage of the stage that featured names like Aykroyd, Candy, and Belushi, Second City Works aims to improve businesses - their teams, their creative thinking, and their strategy. It's a mix of consumer insights, improvised play, and bringing yes, and to the workplace. It is effective, funny, and utterly unique. 

I spoke with Steve about improv and comedy as a learning tool, the story we tell ourselves about our organizations and consumers, and why it's so difficult to give up control. 


Second City Works has been one of my most interesting follows lately. Tell me why your organization has such a unique perspective on the workplace.

For us, improv and comedy are our superpowers. So we use those in the working world to great effect for our clients, knowing that the traditional or conventional way of doing things can feel, from a leadership or even a story standpoint, just absolutely done to death. Everyone is constantly trying to figure what the next thing is, and how to connect, and be in the moment, and lead more effectively. We find that comedy can break down a lot of those conventions. Even though we use it on stage for entertainment, at its heart improvisation is about listening, being in the moment, being other-focused, being part of an ensemble. Those are the things that the working world tends to struggle with, if left to their own devices.

From my perspective, it seems like your programs try to take people out of the traditional roles they play in the workplace and place them in situations they might never have imagined. 

We certainly try and help them give voice to their better angels, helping them lead people. It brings out the aspirational nature of what they want to accomplish at work, or what they want to bring to the world through their business. It’s about not being on autopilot. It’s so easy to stay within conventions, ways of doing things that are firmly rooted. Those conventions make it so easy to forget about why we went to work at our organizations. It can start to feel very familiar - we go back home for the holidays, we play a certain role, we leave. A lot of the roles we play at organizations are almost stock or archetypal characters, as opposed to being a part of more fluid or collegial or collaborative teams. 

"We can tailor all of our communications, all of our social feeds, all of our friendships so that the world starts to feel like everyone thinks and acts like we do."

At its heart, our approach is about really trying to listen to others and empathize with them. I think in the larger world, the research says that we’re just not very good at doing that. It’s the bubble phenomenon - we can tailor all of our communications, all of our social feeds, all of our friendships so that the world starts to feel like everyone thinks and acts like we do. We know that’s just not the case. There’s a bigger spectrum of belief systems and behaviour out there, and overcoming the bubble is going to be one of society’s biggest challenges. We can’t just intellectualize this, we have to really empathize with others. 

Improv seems like a great tool to try and get people to shake off some of that baggage - even if as a writer it seems like a terrifying experience

It certainly is, at least the first time. It gives you this visceral reaction. You’re scared, but all of a sudden you realize I get to play. That reduces a lot of tension, and you get more comfortable. One of the biggest benefits of the social learning we produce through improv is that you can fail over and over again without consequence. That becomes really empowering when you see that you can take chances and be rewarded. It’s a completely different structure for learning in the workplace. Back in our everyday working lives, we aren’t often as safe in that regard. You might be terrified to take risks at work, and you stay in that mode, and it really limits how far you can go.

Is the primary benefit of these programs inspiring people to be bolder, or is it about building up the relationships and teams themselves?

My cop-out answer is that it’s probably a bit of both both. There’s the bonding experience itself. Within the group of people you’ve done improv with, it’s like you’ve all gone off to a playful war together. There’s a lot of camaraderie there, and you’re truly playing together, which accelerates the relationships. That said there’s a huge benefit to trying to get people to be comfortable within an uncomfortable situation. It can be an uncomfortable world, and the truth is a lot of what we do is improvised. The Revolution Will Be Improvised - we talk about it all the time. We play with this theme a lot, about getting comfortable with the practice of being unpracticed in a world that is volatile and uncertain and really ambiguous. We try to diffuse some of that by encouraging the right mentality, instead of always being disappointed or always feeling caught off-guard. What if, instead, we could expect that things are going to get a little weird and uncomfortable and really lean into it?

We’re almost able to take people back to a more open and a more childlike mindset. If you see children taking improv classes, it’s just second nature to them. They’re used to being hyper-creative and playing together, and it’s really hilarious because they’re natural improvisors. We have so much structure and so many responsibilities that we often forget the nature of play, both for fun’s sake and for how much it can help us accomplish. 

I think when people are hesitant to really play it’s because of fear. Fear of looking stupid or not looking capable and confident. A lot of the roles we play at work are designed to make us big and important and smart. To strip all of that away can be scary. 

In our practice, we do see that structure and status and hierarchy can actually inhibit organizations. That’s changing slowly. We see more and more organizations wanting to be flatter, wanting to empower people to make decisions earlier and earlier. Lots of service-based companies want to empower employees to provide service to their customers without having to seek approval to take certain actions. It took a while, but generally organizations are better at it now than even five years ago. I wouldn’t say anyone is perfect - it gets all too easy to fall into the default where the structure is familiar and rigid. 

Why do you think that its difficult to break out of that default?

I think it’s conditioning. If just one business was doing it, it would be pretty easy to leave and go somewhere else. The language and mores of business suggest that you can go into one company and expect a certain thing, and to go into another and expect a certain thing. It’s too easy to tell the story of a big business without ever being human or vulnerable because we’re all trying to show that we’re successful. There’s a lack of genuine identity that makes the whole thing tricky. 

We really want to make work better. We believe that all of the things that individuals can experience in our workshops or classes can be applied at a larger business level to get underneath the aspects of a business that determine who is successful and who isn’t. 

Think about how organizations talk about what they do. Typically it’s some variant of we’re large, we’re successful, we have this geographic footprint, we make these things and they’re always the best. As a consumer we don’t know how much of that is genuine and how much is just spin. From an organizational level, there’s a big desire from the clients we work with - marketing and leadership teams - to understand what their story is and how they can use that story to connect with audiences in more meaningful ways. It’s about making the audience feel like they’re a part of something more like a relationship than a traditional one-way brand impression. 

I empathize with marketers and marketing leaders, because it’s really difficult to do it well. It’s exhausting. You have more channels than ever before. You have so much more content being published - and some of it’s actually being consumed. It’s just so crowded out there, and it’s almost a case of less is more, where you have to look at the big things you want to communicate and how to accomplish that. How do we do that? 

 "It gets very easy to say this is the demographic we’re going after, this is what they look likemaking them an abstraction."

I think of Hollywood. Hollywood is really amazing at recycling ideas and rebooting things. It’s a lot easier - we know what to expect, and we understand story structure, and as an audience they can meet our expectations. Original storytelling is a lot harder, and there’s something a lot like that going on in the business world. Originating something new can be terrifying and risky, but I think that is where more and more of the reward will be. We see that in social and branded content, where it’s the brand that is trying to make wholesale changes that is rewarded for it, rather than just trying to stick with what they know, or think they know, about their consumers. You can’t treat your consumer like they’re in a bubble. It gets very easy to say this is the demographic we’re going after, this is what they look like, making them an abstraction. They’re an audience, and audiences like to be entertained, they like to play. We’ve found that treating the audience as a creative collaborator can help get organizations to that sweet spot, rather than just sticking with the status quo. 

That can be a tough sell to organizations, because collaboration requires giving up some measure of control.

It certainly is. To me, it becomes a question of when you want to give up control. Do you want to give up control now, or do you want to do it later? With our practice, we have an offering we call Brand Stage. It allows a group to try lots of ideas in front of an audience and rapidly prototype how they want to communicate ideas and products with their own community and get real time feedback before they have to commit to it. We find that it’s a very liberating experience for our clients, because they get to try lots of things and fail without consequence, and taking those learnings to improve their work. That’s usually less terrifying than the classic process of strategizing and planning and then presenting it to a world that has never seen it and hoping that it works. I’d rather give up control early if it means I’m getting better information and then have a little bit more control later, because things have been vetted at that point, making the whole process less risky. 

Going back to abstracting your audience, why do you think there is a backlash from audiences or consumers against being categorized into demographic segments?

It’s a tough one, isn’t it? We all feel like we’re distinct, that we’re individuals, that the choices we make are of consequence. When you’re treated just like everyone else, then it feels bad and the whole thing breaks down. The millennial tag has a lot of backlash, which is something I experienced too as a Gen Xer, because it doesn’t feel like you brand yourself with it. I don’t think a lot of folks in that generation use that word in that particular way. I think a lot of them hate that tag. People don’t think that they can paint with that broad of a brush stroke and say that what they’re describing is really grounded in reality. At a certain point it becomes stereotypical, and stereotypes, at best are lazy, and at worst are actually pretty terrible. They simplify and reduce things to the point where they’re not accurate, and that can be hurtful. With the ability to meet people at an individual level and learn a lot about them, we’re being lazy as marketers and people when we do and just try and oversimplify. 

It really conflicts with the idea of who you think you are, the story you tell yourself. I experience my own life very vividly and personally, and being reduced to a category as large as a generation rudely removes that individual identity. 

It’s almost like hazing from generation to generation, isn’t it? Every generation gets stuck with a tag from the previous one, who is in control, who sells the products, who runs the company. It happened to us so now it's happening to you. We never quite get out of that business.I think a positive attribute of “Millennials” is that they’ll call that out. I think that Baby Boomers and Gen Xers are more willing to use those labels. With Millennials and Gen Z, they’re just not using it. They don’t think in terms of the mores of other generations.

It’s so strange because if you look at who controls the conversation online, there’s an argument to be made that many of those conversations are dominated by “Millennials” or “Gen Z”, but those labels still seem to persist anyways. 

I think with a lot of those social platforms, there’s a natural audience of people who go there. Then there’s all of the interlopers who try too hard, who go there but don’t really fit in, that aren’t terribly cool, that think the experience is something that it really isn't. When we do insights work with different audiences, everyone can kind of tell when mom or dad are around and they’re not being cool but they’re trying really hard. There are a lot of brands that are really messing that up right now. There are some that are doing it really well, that are giving control to people who are natural participants for those platforms or communities. You can’t just wander into these things saying Hey isn’t this rad and think that you’re killing it. You’re probably better off not trying, you’re better off staying away and figuring out who you’re really for and what you can do for them. Once you take a step back it’s much better to come back with a bit of humility than just to try and do something that everyone else is doing.

It’s almost better to try and pull of the Jim Gaffigan, self-aware, self-professed lame dad thing that he has going on. 

That’s exactly it. 


You can follow Steve Kakos on twitter @stevekakos

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