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Teamwork: The Improv Approach

Updated: Nov 30, 2023


Teamwork: The Improv Approach - Featuring Caitlin Drago
Teamwork: The Improv Approach - Featuring Caitlin Drago

“If we could all slow down to truly absorb what someone else is saying, it doesn't necessarily mean agreeing with every word but instead seeking the humanity within their words. I'd encourage people to look for something they can affirm or partially agree with. Even if they don't ultimately act on it, their focus shifts towards the positive, allowing them to identify areas of agreement and connection with others.” Caitlin Drago

In her book, "Approaching Improv: Communication and Connection in Business and Beyond," Caitlin Drago shares that the principles of improv aren't just for the stage; they have a remarkable impact on improving communication, teamwork, and conflict resolution within organizations. Improvisation offers a unique, safe space for building trust and rapport, making it a valuable tool for fostering constructive conversations and creative problem-solving, even in challenging scenarios.


Stephen Matini: When did your interest in acting develop?


Caitlin Drago: The earliest memory that comes to mind is from when I was a child. I vividly recall my mom making me a peanut butter and jelly sandwich. I'm not sure if I actually vocalized this or just imagined it, but I would go through a little commercial for that sandwich, highlighting its various components and why it was so wonderful. 


I should probably ask my parents whether this was all in my head or if I was truly acting it out. So I think that's the earliest instance I can pinpoint as the start of my passion for theater.


SM: How did your parents react to your desire to pursue acting? Were they supportive?


CD: My parents were incredibly supportive of my interest in theater and acting throughout my school years. I wasn't heavily involved in school theater during elementary and high school; I was more into the Odyssey of the Mind program. 


This involved a small group of kids, usually around seven or eight, who were given a problem to solve. We would create a skit around it, adhering to specific parameters, timeframes, and budgets. Essentially, we were crafting our own eight-minute play to take to competitions. In high school, I did get more involved in theater, both in school and the community.


When I was deciding on my college major, my initial plan was to study music therapy because I had a strong interest in music and psychology. I thought it was a good blend of both. There was a lot of support for this choice. 


However, when I auditioned for various colleges, I received acceptances from most of the music programs. There was one school that had both a music theater program and a music therapy program, so I decided to pursue a double major. 


Unfortunately, I was not accepted into their music program, but I was accepted for acting. It was one of those moments where I knew I had to give it a try to see what could be. My parents were very supportive of my decision.


After I graduated, I worked in a few contracts with children's theaters. Eventually, I decided to settle down and chose California as my destination. I remember my mom jokingly saying, "You're seeing this through rose-tinted glasses." She's a kindergarten teacher and has those sayings. There was still support, but understandably, she had concerns because I didn't have a job lined up, just a plan to share an apartment with a couple of friends.


Overall, there has always been a lot of support for my various endeavors. When I made the decision to leave my full-time job and start my own business, which I imagine is a similar feeling to what parents experience when their child says, "I'm moving to LA, and I'm not entirely sure what will happen, but this is what I want to do," I was prepared for the typical parental reaction. 


At that time, I was also a parent with a 10-month-old, so I opened the conversation by saying, "What I need from you is your support and encouragement." I could sense my mom holding back all the concerns she probably had and instead providing the support and encouragement I asked for. I'm immensely grateful for that.


SM: So, if your kids decided to pursue acting, would your reaction be similar to your mom's?


CD: I hope I can react like my mom did in the second scenario. However, I also understand what it's like to be a mom, so I'm sure there would be some of that. Yes, I want you to do what makes you happy, but I also want you to comprehend the risks involved.


SM: Do you see yourself as more of an introvert or an extrovert?


CD: As I've grown older, I'd describe myself as an introverted extrovert. I gain energy from interacting with people. If I spend an entire day working from home without any human contact, I tend to feel drained. However, when I'm around a crowd or facilitating activities for a full day, I absolutely need some alone time afterward. Nobody talk to me; let me decompress and be on my own.


SM: I was surprised to discover that many actors in the theater industry are quite shy and introverted, despite the stereotype of them loving attention. What has been your experience working with other professionals and actors in this regard?


CD: I'd say the majority are probably leaning more towards the extroverted side. Nevertheless, there are introverts in the mix as well. I think the crucial skill for actors is the ability to be fully present and focus on the person in front of them. This is a skill that both introverts and extroverts can possess and excel in.


SM: When did you start doing improvisation?


CD: I believe I first dabbled in improvisation during my high school years, likely through a workshop or even during my summer camp experiences. I attended a camp called Theatrics, where we engaged in various theater games. While we were kids back then, I'm pretty sure improvisation was part of the mix, although it wasn't explicitly labeled as such.


I delved into formal improvisation when I lived in Los Angeles, where I grasped the fundamental principles, such as the importance of saying "yes" and building on what's offered, as opposed to shutting down ideas with a "no." 


I attended an audition for an improv character at Universal Studios theme park, where someone shouted, "Make each other look good." This phrase stuck with me, as it emphasized the concept of supporting your fellow performers rather than trying to hog the spotlight. 


This revelation was particularly crucial when auditioning for a job, where some individuals were vying for attention at the expense of their scene partners. Making each other look good made more sense and created a positive atmosphere.


This idea was reinforced when I began taking classes at the Upright Citizens Brigade in Los Angeles. The curriculum had four levels, and the first level introduced the fundamentals of improvisation, emphasizing the importance of "yes, and" and mutual support.


In the second level, we delved into the structure of the Herald, which somewhat resembles the format of a sitcom with interconnected storylines. Working as a team to achieve this without pausing to plan felt like attending a math class, given the formulaic nature of it. However, this structured approach suited me well, as I appreciate having defined boundaries and rules to work within. Just tell me where the box is and what the rules are, and I'm ready to go.


SM: If someone feels extremely anxious about trying improvisation, what advice would you give them?


CD: I would reassure them that improvisation isn't about being funny; it naturally happens because of the rules of improv. Ideally, if you have a great partner, they'll be there to support you. It's not solely on you; we're there to make each other look good. So the more we focus on our partner, the less self-conscious we become. 


Another important point is that we're already doing improv in our daily lives. None of us woke up with a script this morning. I always say it's like honing a tool you already possess.


SM: Could you provide an overview of the rules of improv? You've mentioned a couple of them, but could you summarize them for us?


CD: Certainly, there are two main rules in improv. Firstly, you always say "yes." This means that when someone introduces an idea or concept, you accept it as the idea of the moment and build upon it. For example, if I were to say, "Hey Stephen, I love your red hat," you would respond with, "Yes, I love my red hat, and I'm going to wear it to the picnic this afternoon."


Our natural human tendency is often to say "no," especially if an idea is unexpected or uncomfortable. In improv, this can lead to awkward situations. For instance, if I said, "Stephen, I love your red hat," and you replied, "I'm not wearing a red hat; I'm not wearing any hat at all," it creates discomfort for both of us and the audience. Improv challenges us to skip the "no" reflex and instead focus on "yes, and," looking for what can work rather than what can't. In regular conversation, this doesn't mean agreeing with everything, but rather being present, listening, and adding to the conversation.


The other significant rule is always looking to make each other look good. In improv, we aren't solely focused on being the one to say the funny thing and get all the laughs. A great improviser understands the strengths of their team members and sets them up for comedic moments. In an improv show, the person getting the laughs is a good improviser, but the one setting them up is the truly exceptional improviser. This is the kind of team player we aim to be.


Sometimes we mistakenly believe we have to handle everything ourselves, especially in leadership roles. However, there are people around us with unique skills, talents, and passions. Being mindful and recognizing their strengths and desires allows us to give them opportunities to shine and play a supportive role when needed. When we all adopt this approach, we can harness our creativity and passions with less pressure, more creativity, and a lot of fun.


SM: Why do you think people often appear so oppositional, leading to division and divisiveness? What's your perspective on this?


CD: I believe this behavior stems from our survival instincts, especially when we're faced with stress, which is all too common in today's world. In that state, particularly when our brains shift into "fight, flight, or fawn" mode, our natural inclination is to seek out threats. We might perceive even neutral things as potential dangers.


It's easier to identify what won't work and say, "No, I'm not comfortable with this." It takes conscious effort to bypass that initial "no" response or acknowledge it and let it pass. Instead, we can choose to explore what might work and approach things with curiosity rather than dismissing them immediately.


What's intriguing is that by being the person who genuinely listens to others, even if you don't agree with their ideas, you build trust. You become a reliable source for feedback, helping others identify potential flaws and find solutions. This openness encourages people to approach you with both great and not-so-great ideas.


The added benefit is that they're more likely to come to you sooner when there's a problem, allowing for timely intervention, rather than delaying until the situation becomes unmanageable because of fear of your reaction.


SM: How do managers typically respond to using improvisation as a tool for innovation and collaboration in organizations?


CD: Initially, when I introduce improv, people aren't typically jumping for joy. So, I begin by clearly stating our purpose and setting the boundaries. I emphasize that our goal is to learn, connect, and enhance our communication skills. It's essential to understand that we're not here to be comedians, and there are rules in place. It won't be a chaotic free-for-all. I won't suddenly ask someone to come up and perform without warning.


To alleviate any anxiety, I make it a rule that nobody has to perform on the spot unless I specifically request volunteers to help demonstrate a game or exercise. We conduct activities in small groups or pairs simultaneously, so there's no fear of being unexpectedly called upon to perform without a script.


Once everyone knows what to expect, understands the rules, and grasps our shared purpose, my next step is to introduce laughter. Laughter has a remarkable ability to reduce stress, connect people, activate the learning centers in our brains, and make trying new things easier. It's a vital aspect of improv that continues throughout the entire experience.


Even when we explore situations that hit close to home and have real-world relevance, participants get to practice these concepts in an exaggerated way, which often leads to moments of silliness. They can choose what they want to take away and scale it back to suit their needs. The ongoing laughter keeps our minds open, facilitating learning, connection, and trust-building—valuable byproducts of laughter in a learning environment.


SM: You've trained and worked as an actress for a long time, which makes you a master in emotional intelligence. Acting involves embodying characters and understanding people deeply. If someone lacks emotional intelligence, perhaps due to a lack of self-awareness or difficulty connecting with others, can they still succeed in an improv exercise?


CD: I believe they can. Improv exercises offer a way to increase self-awareness without feeling singled out or attacked. 


For instance, consider the one-word story exercise. Participants stand in a circle and collectively tell a story, each person contributing one word at a time. It's a simple yet engaging game. They can have fun with it, and things might go off the rails, leading to laughter. 


Afterward, we can discuss their experience—what was interesting, fun, and challenging about it. This process allows them to notice aspects of themselves, such as thinking ahead or not paying enough attention to the person before them as they plan their word.


It serves as an entry point to empathy and, by extension, emotional intelligence. Participants learn through their experiences and self-discovery.


SM: How about using improv with a team that needs to improve teamwork and has trust issues? Can you effectively use improv with people you don't trust?


CD: In the context of a workshop, yes, because I ensure everyone follows the rules. We push everything to the extreme, allowing participants to see how the rules work. I emphasize that we are there to make each other look good and to say "yes." 


Even when working with someone they don't fully trust, they can still experiment with these principles. Through the experience of connecting with each other, being present, and adhering to the idea of listening, accepting, and adding to each other's ideas, they have a training ground to begin building trust.


SM: Have you ever used improv with kids?


CD: Oh, absolutely! I have two kids. My son once asked me, "What do you do?" So, I introduced him to one-word story, and he really enjoyed it. Now, when we're in the car, he says, "Mom, can we play one-word story?" We play it together. But aside from the overt practices, kids often come up with their own creative ideas. My eight-year-old, in particular, is full of ideas. I want to nurture his creativity, curiosity, and problem-solving skills.


There are times when he suggests something, and my initial reaction is, "Absolutely not!"However, I've learned to step back and consider, "What part of this idea could work? Can we find a piece we both agree on and build from there? How can I challenge myself to avoid defaulting to 'no' and instead explore possibilities?" I don't want him to think, "Every time I ask Mom, she'll say no, so I'll just stop asking." That would erode trust in our relationship. I seek opportunities to discover where the potential lies so we can collaborate on ideas we both agree upon.


SM: Can improv be applied to address specific team issues or dynamics that the team is struggling with, such as interpersonal conflicts or other challenges?


CD: Yes, it is possible. In my program, we start with the fundamentals of improv, and then we build on that foundation by incorporating skills people might already have, like handling difficult conversations or giving and receiving feedback. We explore how the improv approach can enhance the effectiveness of these conversations.


Regarding conflict resolution, I typically ask participants to share their experiences with conflicts, whether within the team or with external parties. We then use improv to define mutual goals and practice the "yes and" approach during the conversation. What's exciting about addressing conflicts this way is that it encourages people to actively listen, understand each other's perspectives, and work collaboratively toward a solution. This approach often bypasses finger-pointing and fosters a more cooperative dialogue.


Another method I use is a game called "worst idea." When there's an interpersonal conflict or a complex issue, people often feel pressure to come up with the best solution immediately. By asking them to share the worst idea they can think of – something so out of the box it might get them kicked out of the company, for example – it shifts their thinking. The challenge then becomes identifying a tiny spark of an idea within that worst idea and building on it to gradually develop a feasible solution. This approach eases the pressure of needing to come up with a brilliant solution right away and encourages exploring unconventional solutions to sticky problems.


SM: How did you come up with the idea for the title of your book, "Approaching Improv: Communication and Connection in Business and Beyond"?


CD: I've wanted to write a book for a while, but I wasn't sure what it should be about. I felt pressured because there were already books about using improv for communication and its application in business. I thought I had to come up with something entirely new. 


However, during a conversation with a friend about writing a book, I shared my dilemma. My friend gave me the permission to write from my own perspective, with my stories and insights, tailored to the people drawn to my teaching style and approach.


Once I had that permission to write something in a similar vein to existing books but with my unique perspective, I felt liberated and enjoyed the writing process. While many people find writing to be a drag, I personally liked it.


SM: You focused on enjoying the learning process rather than fixating on the final outcome, which is a great approach to any project.


CD: Absolutely. Once I shifted my perspective to think about who this is for and how I can help them, it became less about creating something brilliant and more about creating something helpful.


SM: If I were to read your book, what do you want me to gain from it?


CD: I hope you can gain an understanding of the basics of improv. This involves grasping the significance of leading with a "yes and" mindset and the concept of making each other look good. What are the implications of this approach, and how can you implement it? Putting it into practice has various ripple effects.


As I mentioned earlier, I want you to apply your existing knowledge of communication skills such as giving and receiving feedback, handling difficult conversations, and navigating change, and use the principles of improv to enhance the effectiveness of these interactions. Additionally, I'd like you to consider the broader cultural impact. How might this approach be applied on a wider scale, either within a specific culture or across an entire company?


I also want to provide you with some encouragement because I understand that this isn't always an easy endeavor. In improv, we have a concept called "follow the fear." It means that if you have an idea that feels a bit daunting, instead of letting fear paralyze you, you step into it and share it because it's necessary.


I titled this discussion "Approaching Improv" because I acknowledge that it may not be the simplest task. My aim is to make it accessible, something that anyone can grasp and apply immediately.


SM: What's the key message or insight that you'd like our listeners to take away from our improv podcast episode?


CD: I believe that, especially when it comes to something dear to me, the essence lies in people connecting through active listening. If we could all slow down to truly absorb what someone else is saying, it doesn't necessarily mean agreeing with every word but instead seeking the humanity within their words


We should employ our empathy to comprehend their perspective and search for common ground, even if it's hidden beneath the surface. This way, we can foster connections through listening. An actionable step for those listening to this is to consider that you can't genuinely say "yes" to something you didn't really hear.


I'd encourage people to look for something they can affirm or partially agree with. Even if they don't ultimately act on it, their focus shifts towards the positive, allowing them to identify areas of agreement and connection with others. That's the practical step they can take today.


SM: I hope your book finds tremendous success with its readers. Thank you very much for sharing this important conversation with me.


CD: Thank you for having me.


🎧 Listen to the episode on Spotify, Apple Podcasts, Amazon Music, Podbean, or your favorite podcast platform.



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