What Improv Comedy Taught Me About Building Products 🎭

My improv-inspired mental models for product management, start-ups, and life.

What’s poppin’? A warm welcome to all the new subscribers that have joined Sam’s Sandbox since the last issue. Astute readers might notice that this topic is a departure from the typical wellness content. My intent with this longform piece is to invite you into the universe of my favourite creative passion, and reveal the associated principles that have changed my life.

I often get asked about my improv background during icebreakers, one-on-ones, and interviews. It’s not a common hobby among business and tech folks in my immediate environment — I tend to gloss over the details to avoid unleashing an unsolicited technical comedy meta-analysis. If I sense continued curiosity, I point to my favourite metaphors curated from my past instructors and domain experts:

Improv is group mindfulness. Improv is yoga for your social skills. Improv is practice in being a better human being.

A continuous stream of high-fidelity conversations sparked my willingness to bring these airy-fairy claims to life. At the tail-end of March, I ran my last workshop of a three-part improv comedy series for On Deck’s (OD50-1) world-class operators and tech superstars. My ultimate goal was to create a lasting impression and appreciation for the broader discipline of improv.

I decided to integrate a systems thinking approach to my teaching, connecting the disparate themes learned through years of training at The Second City and exposing these models into the air. If I could strike the sweet spot of presenting lighthearted, yet stimulating exercises, the real gratification would come from pooling everyone’s collective energy and releasing it.

For me, the biggest dragon to slay in this creative process was: How could I coordinate improv to contain the chaos, while retaining the primary goal of just saying yes to play?

Inspired by Lenny Rachitsky’s inventive piece on “What Buddhism Taught Me About Product Management”, I’ve reflected on my workshop content and the transferable elements of my improv training that have explicitly enhanced my life. This piece is organized by a theatrical classic: the three-act structure that dives into the anatomy of a scene, stretches these first principles into product building blocks, and reveals how to live mindfully through an improviser’s vantage point. Let's start our performance!

I. The Operating System of an Improv Scene

The general flow of an improv performance follows a simple pattern: the performers ask the audience for a suggestion (a word, prompt, topic, theme) and the troupe constructs a series of scenes over the next ~60 minutes. What ensues is a fast-moving conveyor belt that converts dynamic inputs from the actors — anything from lines of dialogue, body language shifts, character behaviours — to outputs dressed up as coherent live-action stories. You might even be treated to song or dance! This form of comedy encourages suspension of disbelief with a healthy dose of relatable realism, as the improvisers strive to provide a mirror reflecting everyday human interactions.

Countering Comedy Clichés

Improv is not about making people laugh. Improv is not just for loud, extroverted personalities. Improv is indeed spontaneous, but not at the expense of its systematic nature. In many ways, you don’t even need to think quickly to become a truly skilled improviser. As eloquently expressed by blockbuster comedian Keegan-Michael Key:

People think that improvisation is moving forward. What improvisation really is, it’s walking backwards. It’s backing up that gives you discovery. People always go: “I can’t think that fast!” No no no — don’t think that fast. Just listen to the last thing they said.

Key flips the conventional thinking of improv comedy on its head and carves out an opportunity for the average layperson to pick up the ball and just play. There’s a sense of immediate intimacy that you feel by being part of this ecosystem. The feeling that everyone has the potential to be a world-class listener. To improvise is to listen. These observations suggest that improv is nuanced: an intricate web of well-documented, on-stage rituals hidden underneath the clutter of slapstick bits and artificial plot twists.

Systematizing Improv

Making sense of this wacky world involves recognizing the breadth of technical tools available to the seasoned comedy practitioner. Before we can boldly assert that these skillsets are highly applicable to our personal and professional lives, we need to understand the foundational building blocks that underlie improv comedy at its core. To give you a taste of the on-stage magic, I’ve outlined six of the most salient features:

At a basic level, the concept feels obvious but the practice seems dubious. Improv is fleeting, messy, chaotic. How might we systematize such a thorny transient activity? My scientific scholar mindset yearned to create order from the chaos, resulting in the above improv mental models. These frameworks provide the interactive infrastructure and constraints to anchor this artform.

Embracing “Yes, And”

The principle of ‘Yes And’ is considered by many as the ethos of the improv manifesto. The root: I accept your offer, and here’s how I’m adding to your thought or idea. The elegance is literally baked into its powerful simplicity — I consider this model as the lifeblood that flows into and adds strength to the other five mental models.

We develop a platform of a scene through repeated application of Yes And. We reinvest into each other’s choices, creating a virtuous cycle of ideas. We discover the unique patterns and games to play by using these two words, often not said outwardly. Yes And provokes the exploration of human behaviour and shows the subtext of the characters’ motivations from each back-and-forth conversation.

The comedic construct of Yes And stretches beyond the performance stage and seeps into our everyday interactions and relationships. In typical systems fashion, I argue that this pervasive phenomenon can be visualized through a theoretical 2x2 matrix:

Getting caught in the minutiae and mundane within our busy worklives muddles the immediate benefits of adopting the Yes And mentality. In my view, we tend to oscillate between being a passenger and a driver in the long-tail of our decisions. Worse yet, moments of pressure often strain us to become a blocker unconsciously. To work out our builder muscles, we can consider actively embedding generative practices into our daily flow, which can consist of writing, debating, pitching, or meditating.

Advancing the Story

If Yes And represents the units of comedy creation at an atomic level, then the sum of the parts naturally flow into a full-fledged story. The last step in our analysis is mapping the chronology of a scene and sequencing each mental model as appropriate.

We can think of improv platforms as a diving board that submerges us into different swimlanes comprised of three fundamental questions: what, who, and where. While the conventional mode of thinking stresses spontaneity and randomness, establishing a robust platform helps contain the scene with constraints. In other words, while there seems to be boundless possibilities of ideas at the outset, improvisers can only build based on all available information accumulated at the current moment.

If you have a background in data science, you’ll recognize this concept: this is a decision tree. Each subsequent node represents a singular unit of information presented as a gift to the other person. But just like statistical decision trees, there is a risk of “overfitting” an improv scene. Imagine one improviser compromising the character discovery with a misaligned reaction, or attacking the integrity of an established relationship by aiming too tightly or boldly at an over-the-top gag.

Structure is king, and the most memorable stories in life always bring us along for the ride — making us feel something. This is an improviser’s ultimate superpower.

The main takeaway about this operating system is that top-level improv encourages open-ended storytelling between scene partners in the frontend, while facilitated by microscopic observations, choices, and connections running in the backend.

II. The Scenework Principles for Products

By pushing improv to its logical extreme and the highest level of abstraction, we can start to appreciate its value when applied to disciplines like product management and start-up strategy. According to Bob Kulhan, a business professor at Duke University:

Improvisation is being super-pliable. Entrepreneurs and product leaders need to get out of their own way and adopt a fail early, fail often mentality.

Almost counterintuitively, improv teaches us to impose limits on our innovations as we wade through the neverending downpour of pending tasks and unbuilt features. It acts as a forcing function for creativity and serendipity. For product leaders, the improv mind can be applied to mimic customer experiences and pain points to better empathize with how the end-product will be touched, felt, and perceived in the wild.

One question that both budding entrepreneurs and technologists commonly face in developing cutting-edge solutions today: How do we build a creativity engine that enables consistent imagination and invention? I’ve explored this space in specific contexts of three builders: product designers, user researchers, and software engineers.

Design thinking

Design thinking is an ideation approach that emphasizes human-centered, creative problem-solving through making connected choices. The illustrious Creativity and Innovation Management journal published a model in 2018 called design improv, a methodology for operationalizing improv principles in early product development:

The emergence of an innovative product design can be compared to the telling of a funny joke: both combine seemingly unconnected ideas in a way that is both surprising and satisfying.

Humour is directly integrated at the heart of this unorthodox process, formalized through a set of workshops. Researchers and designers apply comedic devices to the initial discovery phase, such as stitching together visual comic strips for product use cases and playing short-form improv games as fuel for inventive stimulus.

The most important callout is the heightening step, my all-time favourite tactic to apply. The premise is elegantly simple. Once you’ve noticed what stands out as being unusual (an atypical customer pain, a reconfigured feature, a branding preference), candidly ask yourself: “if this is true, then what else is true?” This prompt pushes us to be possibility thinkers and inflate what is already absurd to drive out-of-the-box outcomes. It’s this exact transition between expansion of thought and recursion of technique that grants us the liberty to build even bigger and bolder.

Further literature also validates these parallels between performative improv and product management, specifically cultivating active listening to empathize with human needs. Cedric Chin contends in this blog post that Amazon’s Working Backwards method quickly allows the company to rapidly bet on and validate new products. The technique tells team members to visualize the ideal customer experience by fleshing out a future-facing press release and drafting a mock FAQs page.

User testing

As we learned earlier from Keegan-Michael Key’s analogy, improv is all about walking backwards to drive discovery. We willingly flip the script and reverse engineer from the aspirational end state. In this case, product management is not approached with the classical blue-sky, blank-canvas, feature-driven approach. Instead, user obsession takes precedence and every decision is laced with feedback and hyper-observation.

By a former Intercom ex-product manager and fellow improviser:

Don’t just listen and act quick. Try and digest the motivations behind what you’re hearing - the pain behind a customer’s feature request, the rationale behind UX changes a designer is sharing, or the new technology that inspired a feature suggestion from engineering.

This layers the improv models of discovery and subtext into the fundamental activity of user testing. By diving into human motivations beyond what is stated, you can create a new sense of clarity and convert constraining conversations (“No it’s not possible - the tech stack doesn’t support it!”) into value-enhancing dialogues (“Great point - how might we prioritize these pain points and requests in our issues backlog?”)

Even with these proactive principles in mind, product managers should not say yes to every single idea, feature request, or piece of user feedback. Capacity, cost, and culture still constrict what is actionable. Similarly in improv, agreement is not the same as acceptance — we don’t have to blindly say “yes” to candidly accept a point-of-view. As banal as it sounds, the most important highlight is to never let go of an empathetic and experimental mindset when building products to delight and excite eager customers.

Extreme programming

The last unconventional connection we can bridge is the overlap between improv and software engineering. In any common-day tech hub, you’ll hear the words agile development being thrown around, whereby moving fast and shipping small reign supreme. Extreme programming (XP) is a variation that emphasizes responsive rapid releases to customer needs, governed by several stage-gated feedback loops.

Just like a performance starts vague and high-level, XP works down from a macro monthly release plan down to micro hourly testing. One software principle that perfectly fits the improv system is pair programming, where two engineers work jointly on the same code. While the first developer focuses on building the code base, the other reviews it, suggests improvements, and debugs mistakes throughout.

The spirit of continuous integration and continuous delivery from two developers constantly committing code is akin to the dynamic nature of two on-stage actors developing deeper dialogues.

If we really wanted to get programmatically-philosophical, we can argue that improv choices are a series of algorithms. We imagine an infinite game of constant learning, where scene partners work together to gradually figure out the branching logic of characters and environments. For those intrigued about this extra technical territory, the application of Markov chains in probability theory deserves specific attention.

III. The Improviser’s Lens to Living Life

As a huge proponent of finding unconventional ways to live mindfully, improv principles fit snugly into various applications. Within three core themes of wellness, empathy, and play, I’ve curated a list of resources that echo the various use cases:

🔑 For you: Improv as a wellness modality

  • A form of therapy: By creating a space free of judgment and free of failure, the stage can offer a collaborative catharsis for people struggling with anxiety.

  • A form of uncertainty management: By assembling a scaffold of workflow adaptations and personal practices, improv principles act as reassurance.

  • A form of addiction treatment: By actively fostering unrehearsed interactions, improv exercises boost self-awareness and addiction recovery rates.

💛 For others: Improv as an empathy catalyst

  • Empathy within interpersonal relationships: Whether in the workplace or in romantic endeavours, improv finds a place in positive psychology relating to expanded empathy, immersive mindfulness, and constructive responding.

  • Empathy in the age of virtual meetings: Social organizational psychologists at the Kellogg School of Management explore the hurdles of cross-talk and low empathy on Zoom calls with six improv devices.

  • Empathy for essential service occupations: Particularly in the medicine realm, there has been extensive research into improv’s role in augmenting soft skills like empathy for doctors and medical practitioners.

👶 For all: Improv as a formal license to play

  • On laughter and learning: “The key is using humour to enhance otherwise dull statistical methodology by tapping into students’ multiple intelligences…”

  • On permissionless living: “Play gives us permission to be other than who we are in ‘real life’. It allows us to imagine ourselves as being, feeling, and doing different...”

  • On playfulness: “It’s time we stop seeing play as subordinate, and start getting serious about living a playful life. Playing opens up a new time and space…”

If you’ve stuck around to the end, I really appreciate you letting me gush about improv! Feel free to shoot me a message if you ever want to talk performing arts or products :)

To end with a comforting philosophy from a budding improviser to all of you: “I got your back!”