How Improv Transforms Teaching, Learning, and Parenting with Will Dennis

Hello parents and teenagers, this is Shellee Howard, the founder and CEO of College Ready, and today I have a wonderful guest, Mr. Will Dennis. Welcome to the show.

Thank you so much for having me, Shellee. I'm so excited.

You got it. Well, can you introduce yourself, give our listeners a little bit of your background, and, uh, what we'll be talking about today?

Yeah, for sure. So as Shellee Howard mentioned, my name is Will Dennis and I am, I'm a 12th grade teacher at a private all-girls school and I'm also the owner of an improv company, Unscripted Productions, that specializes in applied improvisation. So while we teach the skills of improv, we really focus on how you can transfer those skills into whatever you do in life. So we work with companies, we work with teams, and we work with students and educators to help parlay the value of improv into the educational setting.

Oh, that just unpacked a zillion questions for me. Listeners, I hope you're with me. So the first question I want to know is, when you were in high school, did you think you would go into improv and be a teacher?

Uh, no. I think, you know, when I was in high school, I didn't know what I was going to do, and I, I benefited The high school I went to was incredibly good at developing character and character development and critical thinking so that when I left high school, I didn't feel like I needed to have the answer of what I was going to do. I was confident that I would be able to figure out whatever it is that I did, uh, ultimately. So that was a real gift for me. So I was always involved in the theater program at high school, and we had a top-notch theater program. It was one of the best in the area, and that sparked my interest in improv. Of course, it's sort of like a natural— it's like a cousin of theater and musical theater. And I think I probably became a teacher because of the teachers that I had. So I didn't set out to become a teacher, but when I got to college, I still didn't really know what I wanted to do. I was undecided, and I got to a point where I had to decide, and I looked around, and all the most influential people in my life were educators. And I went, okay, well, I wanna emulate the people that I love and that I adore. So let's see if this thing works out. And it did.

Outstanding. So next question is, how did you choose, or did improv choose you?

Yeah, so I guess, uh, the short version of this story is that it was a circuitous route to the classroom, and I was doing a number of other things. And I worked as a professional actor for a period of time. And the thing about that is it's similar to teaching where it's hard to make a living on just that. So there is a theater that I was performing at a lot, and they had reached out to me and said, would you be interested in teaching a class? So they're trying to create new revenue, find new patrons. I'm trying to make some more money. So I was like, yeah, sure. Why don't we do it on improv? It had been at that point the nature of most of the performance that I was doing. So we taught that, and that's when I started to go, oh, okay, there's something different here. This isn't just fun. This isn't just performance. This is changing me. And as I teach it, it's changing the people who are taking this class. They're starting to see the world a different way. They're rediscovering themselves. They're rediscovering their self-confidence. They're rediscovering all of that. And so I fell in love again with that. And I, you know, I say it sounds dramatic or it sounds, you know, a little pie in the sky, but it was through that experience that I understand my own personal mission was that I believe that improv can change the world. And then I set out to start changing it however I could.

Okay. So how did you connect the dots between 12th grade all-girls classroom and improv. How did that come together?

Yeah, I think, I mean, part by accident and part intentional. But it was, you know, when I, when I arrived at the school where I am now, all-girls school in Bucks County, Pennsylvania, Villa Gessmer High School, if anyone's interested, it's phenomenal, phenomenal school if you're on the East Coast. And when I arrived there, I had not been in the classroom for a little bit of time. I had worked in fundraising, and then I was working as a professional actor, and then Circuitous Route landed me there, and I didn't know how to do anything else. I just leaned into what I, what I knew how to do. I leaned into my authentic self, and it had always been my educational philosophy to be as much who I was as a human being and to show that to my students. So it just started to make sense. It became my classroom management practices because the beauty of improv is that it levels a playing field so that in a classroom where you might have students who are high achieving and then students who learn a little bit differently in the same room. Improv's an equalizer so that everyone has a safe space to be who they are and to grow the way that they grow. Like, nobody is rewarded for being a really good test taker in improv. Nobody is rewarded for being able to memorize in improv. Nobody is rewarded for how fast they read in improv. So all of a sudden, all of my students were feeling safe in my classroom. And I went, this is great for classroom management. And then we started flexing into some other ideas and really building, you know, the real connection is between— there's a lot of energy around social-emotional learning and growth mindset right now, as there should be. And like, that's where the connection is because improv teaches us to understand that our mistakes are opportunities for growth. It teaches us to be willing to support the people around us and not always to have to be in the spotlight. It teaches us to be radically accepting of one another as human beings and then contribute something to every community that we're a part of. And it teaches us that we don't have to have all of the answers. And this is the one, Shellee Howard, that I love the most when it, when it comes to working with 12th graders, is that oftentimes schools can be really high-pressure situations and spaces. And students think that they need to know everything the minute they walk into a classroom and that they have to have all of the answers and they have to know exactly what they're going to do at every given point in time. And they know their future and they know it and they know it and they know it and they know it and they know it. And it becomes this powder keg and it's just a recipe for a breakdown. And what improv teaches us is we have a phrase, bring a brick, we'll build the cathedral together. And it gives young people the permission to just be who they are and what they do well and contribute that and recognize that if they can do that, then it makes space for the people around them to also be their authentic selves and build upon the foundation that they've helped create. And then that foundation gets stronger and then they get to build upon that. And like everybody ends up being okay and being better off if we just give ourselves permission to not have to have all the answers and just to do the thing that we do and do it really, really well.

Oh, there was a lot in there. Sorry, powerful. Well, you know, I, I work with teenagers all day long. That's what I get to do as well. Um, minor, male and female, um, from middle school all the way through college transfer students. And the one thing I will— I have recognized is these kids come very full of pressure. Like, their pressure is so insane. Some of it's internal, like they just expect themselves. Others external, like the expectations. I'm guessing that improv almost allows the, the lid to just be just tilted enough to be like, I'm gonna be okay.

Yeah. Yes, absolutely. Yes. And what it does really really well is that it kind of celebrates the opposite, right? It celebrates mistakes. It celebrates imperfection that becomes gold in improv. And when you do it over and over again, when you build it in as a practice, it allows you to recognize that so much of your success can come from outside of those expectations or pressure to be perfect. So yeah, it it opens that lid a little bit and just lets the steam out in a way that, look, at the very least, if you can laugh, you're doing something for your own psychology and physiology, right? And like oftentimes improv lends itself to laughter. So like that is a gift and you get to laugh at yourself, which young people don't really get to do anymore, right? Like, oh my gosh, we live in the world of social media. So it, it, you can only not laugh at yourself. You can't put yourself out there anymore. So there's these pressures that are external and internal, and then there's this fear of judgment. And that's another thing that improv just completely dismantles, because one of the things we talk about is being willing to make everyone else look good instead of make yourself look good. And if you do that, I promise you, this is like— this has been my own best therapy, is if I focus on making everyone else look good, I don't have time to be worn down by my own insecurities. I at least get a break. You know, I often, when I teach an improv class, I joke that, you know, for 2 hours I'm focused on making everyone in this room look good. So I'm not thinking about my insecurities. Now I'll get in the car and drive home and, you know, they're waiting for me and I'll, you know, cry my way home. But nonetheless, like, just to get that break because young people don't get a break. It's a different world. It's constant. We're connected and that break doesn't exist. And there's just a series of reminders. Of that expectation we're talking about. So yes, you're absolutely spot on on your instinct that improv helps by being a release valve, but also helps build the habits of understanding that imperfection is the expectation, right? It's progress. We're talking about progress, not perfection.

Yeah. I'm an entrepreneur, and our mantra is fail forward.

Right?

It's gonna happen regardless if you want it or not. So how, how are you going to learn from it and move on? Um, and I often help my students understand, but they're like, but I don't even wanna fail. And then I, and I'm like, well, you are alive and it's gonna happen at some point. And so you might wanna practice what's gonna happen when you do fail. So In our program, we do something really unique. Where you use improv, we use community service. We take the focus off of the student and we put it on somebody they want to help, somebody they want to make their life better. So interesting enough, I see a parallel. We use community service to take that pressure off because they don't have to be perfect to serve their community because they were no better off prior to that student getting there. So I love how the two really support each other. And what we're trying to do is allow that, that child, that teenager to, to be okay with being okay.

Yeah.

And it's really interesting that you've been able— so what does it look like in your classroom is what I wanna know. Like, are you standing up with a microphone and you're just having a good old time and, and making jokes? Or what, what does improv look like in, in the classroom?

Yeah, no. So no microphones whatsoever. But it's actually a tough question to answer, believe it or not, because it looks so different as sort of a year goes on. So in the beginning of the year, it's really, really, really small opportunities to take risk, to fumble, and then to succeed. So it's trust building in the beginning because you can imagine a group of 17-year-old girls coming into my classroom like, cool, now we're going to do improv. Like, no, no. Who's this dude? This is not going to happen. So it's things that don't even look like improv. So it's, you know, here's a classic example. So this is an exercise that we do in the classroom. My school actually has me do it with every first year that comes in. So every 9th grader. And it is something we do with every single corporation we work with. So like Fortune 500s, organizations, nonprofits, teams. And it's a simple round of what we call Epic Rock Paper Scissors.. And it's just you square off against a partner in that game. But the minute that you lose, if it's— if you don't win, you need to become the other person's hype person or cheerleader. And then now as a team of 2, you need to find another team of 2 and you square off against them. And now one person is going to win. And now 3 people have formed a hype team for that person, and then they find another team of 4 and it keeps compounding. Until at the end of it, there is one person who won and everyone else ended up on the winning team because they were willing to shift into a role of support. So, like, it's just setting that as base level. Like, hey, this is how we're going to proceed this year, is like, we're going to support one another, and when we do, we end up on the winning team. And then it starts looking like some silly exercises, like warm-up games where you got to yeehaw and send a lasso around a circle. So, like, they're starting to do these things that are slightly outside their comfort zone. They have permission to be as big or as reserved as possible, but they're just seeing continuously, okay, I just acted like a cowboy or cowgirl sending a lasso, and I'm okay. Like, we're all okay. We're all still here. We laughed together. I did not feel humiliated. I did not feel embarrassed. If anything, I'm starting to feel more connected to the people around me. So it looks like these small incremental things. And then by this point in the year, we've started to introduce like games, right? And sometimes it's just a brain break. It is just that opportunity to decompress because they need that in their day. It's go, go, go, go, go, go, go. And then the other times, believe it or not, like you use it for content. There are games that we use in for review all the time. So for, there's another quick one. It's a game that we play often where you get 3 students up, they stand side by side and they need to be an expert in something. Okay. But they're one expert, so they need to formulate sentences just one word at a time as 3 people. And then we, we turn it into a game show so that I'll be the host of the game show. If we're reviewing, then they're gonna be an expert in whatever the content area is we're trying to learn. And it's impossible. It is almost impossible for them to answer every question correctly because it's 3 people trying to do it. So the minute you think of a word, it disappears because someone said something else. So it celebrates the mistakes in learning because we get to laugh at the fact that it's really not even possible to be successful. And then as the rest of the class is the studio audience who's asking questions, so they get the chance to redirect and try to make correct the mistakes that the players were happening. And then all of a sudden an entire group is learning together instead of this sort of isolated, siloed, individualized learning.

I'm thinking when I was in college, I was on the speech and debate team and we did a lot of similar things because we had to be ready to think on our feet. And so I do— this is all coming back to me. And at the time I really disliked it because it was uncomfortable, right? It's uncomfortable to do something out of your comfort zone, but that's what speech and debate is. That's, you know, that rhetoric, that competition. How might a parent who's listening to this podcast take something from you and be able to share it with their student to help them get there? Not every child can go to your college, especially on the East Coast. So what else— what can you give them as an opportunity to tap into their child?

Yeah, so, so much is the answer, but I'll give you one thing. So the golden rule of improv is a phrase, yes, and. The way that we define it at Unscripted Productions is radical acceptance and contribution. And it means acceptance of one another as human beings with dignity, but it also means acceptance of our given circumstances and our realities. And it is a phrase that can absolutely change your life if you start using it. And so for parents, my recommendation— I'm a parent as well. My children are younger, 5 and 3. But yes and has been the best gift for me as a parent. And I think especially with teenagers who are 16, 17 years old trying to start this process, a process that is so overwhelming and daunting, is to— if you can adapt a yes and mindset and start by just using the phrase yes and, and then I'll give you an exercise. But if you're able to accept the given circumstances of your teenager and you're able to yes them and then add and contribute to their reality or their perspective, you're gonna do, you know, communication crisis management 101 is validate somebody's concern and make sure that they feel seen and heard. And teenagers need this more than anything. It's just so hard to do it with them. Because as parents, we're going like, wait, but like, we know, like, we've been here, like, we're trying to help. And they don't want our help, because they're trying to figure out what does it even mean to be like my own self in this world? And like, I think I want this, but I actually don't really know who I am yet. I'm still figuring that out. And like, what So a real quick exercise, and this will be uncomfortable to do with your teenager, especially if it's like out of the blue, right? You go home, you're like, all right, we're gonna do an improv exercise. But it is such a helpful exercise to understand the value of the phrase yes, and. So real quick, it is a 3-round exercise. You can do it however you want, but each round, as a team of 2, you need to create something that has never existed before. So you can pick, it can be a kitchen appliance, it can be a bicycle, it can be, uh, you know, an iPhone app. It doesn't matter. Just pick a thing to create 3 different things for each round. The first round, give yourself 60 seconds. Somebody has the first idea and then every response needs to begin with the word no. Okay, so you have 60 seconds to come up with an app together, but every response needs to begin with the word no. Spoiler alert, it's not possible. You're gonna end up with about 16 first ideas. You can't move forward if you keep saying no to one another. Second round, same thing, new thing that you're creating. Give yourselves 50 seconds. Every response begins with the phrase, yes, but. Yes, but. And you start unraveling just how dismissive and negating that phrase can be. Right? So, like, we think that we're offering some level of acceptance, but the minute we say, but it's that old adage, right? When there's a but in a sentence, you don't hear anything that came before it. You only hear what came after it. And how we use that when we are trying to help someone because we think we know what's best, right? But it ends up shutting down the other person's given circumstances. Third, pick whatever you want to create. Oftentimes I do a roller coaster because It's fun roller coaster that never existed before. Back and forth. Every response after the first idea begins with the phrase yes, and, and here's what's gonna happen. You're gonna end up with the most unique, creative, innovative, wildly fun, ridiculous roller coaster that has ever existed. And if you look back, you go, okay, great. When I entered into a process of discovery, a process of creation with another person, and the rules were that whatever we say is going to be accepted, and then I'm going to try to make it better. Completely changes perspective and mindset, and it gives young people who are filled with angst and uncertainty and confusion and trying to figure out their place— it gives them permission to have ideas without them being rejected. And then you'll get to a no at some point. Like, you're going to say no at some point, right? It's going to happen. It won't happen in the exercise, but in life it's going to happen. But we've given space and we've given opportunity for people to feel seen and heard. And I think, look, I don't know, but I think that's what teens are really craving more than anything at that point in their lives because of the dynamic of burgeoning adulthood, is to be seen and heard as a young adult and to have their opinions validated, even if they don't ultimately come to fruition. So yes, parents, that was a really long example of telling you, like, If you adopt the phrase yes and and the mindset of acceptance and contribution into your conversations with your teens around college, it will improve the process.

So powerful. I'm going to share another one, parents, just real quick. And Will, you may— you, you can borrow this one.

Love it.

We, we play a game to help students understand financial literacy because many students will say, I want to go to UC Santa Barbara, and I'm like, Awesome. Why? And they said, have you seen the view? It's amazing. And I'm like, yes, but why do you want to go to UC Santa Barbara? And they go, I just told you. And so there's no connection between college and getting accepted and paying for it and graduating and so on. So we play this game with them to help them get clarity about themselves. It's called the Millionaire Game. You have parents. The only rule is you cannot talk during this time or answer for them because you're like, oh, there's— it's devastating sometimes what they say. So I say to them, if I give you $1 million cash, and if they're not smiling, I'm like, whoa, this is a lot of work coming up here, right? Because they're not impressed with $1 million. Um, but I, I'm like, for the ease of this game, let's go with $1 million. If I gave you $1 million and you had 24 hours to spend it, or you had to give it all back to me, what would you do with it? And you're, you're watching, it's processing. I said this last night to a student and he said, well, I buy 3 cars. I'm like, 3 cars, okay, what kind of car? And right, we just started, we just started kind of I said, okay, right? That was my— I'm affirming you. Let's do this. And he went on and on and on about the color and the make and the da da da. And I— and he was going to spend the whole million dollars on 3 cars. And at the end, I said, so which one are you going to live in? And he's like, ah. So it was a really nice way of opening up their mind and accepting what they're saying. Without shutting them down or saying, you don't need 3 cars, right? As a parent, I would have said, you don't— you can't drive 3 cars. What are you gonna do with— like, right? I would have shut them down. But instead, I affirm them and just play right into it.

Yes, yes.

And that is a beautiful thing, as you just showed. And you could do this— I always say it's a very fun— when you sit down at dinner And the younger kids are listening to that. You're so a little young, but the younger ones are listening to it. And then parents, you really find out, are they financially literate? Do they understand, um, you know, going into $300,000, $400,000 in debt for a botany degree? Like, sometimes you're like, whoa. And so it's, it's a, it's a good barometer to use because our goal here is, right, to prepare them for life, as you stated. And if they can't answer how they would use a million dollars, imagine what it's going to be like when they leave for college and they have a budget. And that's really scary. So I love what you're doing. If somebody, a young adult, a corporation needed this kind of support, how could they reach you?

Yeah, for sure. So you can connect with me through our website, which is www.unscriptedproductions.com. We have a number of forms that you can reach us through there, like any website, or you can email me directly. And my email is will@unscriptedproductions.com. And yeah, we'd be— we travel, we're happy to help. You know, we're happy to be a resource. It's my two worlds collide between improv and education.

So Wow. I, I just have to say I'm a little jealous of the, the girls in your classroom because none of my teachers were that cool. So, Will, thank you so much for being on this show.

Thank you. You're so kind.