John Krewson is the author, with Rob Kutner, of the new book Pitch, Sketch, Launch: What Sketch Comedy Can Teach Us About Product Development. Krewson is the founder and CEO of Sketch Development Services. He's based in St. Louis.
Q: What inspired you to write Pitch, Sketch, Launch?
A: I left the comedy/performance world for the software world. Early in my career, I felt like I had to play the part of the straight-laced corporate manager. But as I became more comfortable in management roles, I started to notice that I was relying more on my training as an actor and comedian than any corporate management training I received.
That led me to an insight: the teams that build the best products work a lot like the teams that write the best sketch comedy. They iterate fast, they don’t get too precious, and they rely on each other to take something half-baked and turn it into something remarkable.
I wrote Pitch, Sketch, Launch because I wanted to make that connection explicit—and to give people trying to manage the development of a software product a more human, creative way to think about how they build things.
Plus, it was a good excuse to tell a few stories about Saturday Night Live without seeming like I was just name-dropping.
Q: How did you and Rob Kutner collaborate on the project?
A: Rob brought true comedy credibility to the project: he wrote for Conan and the Daily Show, and he teaches sketch comedy writing at Loyola Marymount.
I knew enough about the inner workings of Saturday Night Live due to my short stint there and my independent research, but Rob was able to bring a wealth of additional insights about the business of creating sketches.
We collaborated with a highly collaborative and iterative approach (go figure), building in small batches, refining, expanding, and spending a lot of time exploring the overlaps together.
Q: What do you see as the connection between sketch comedy and software development?
A: Good sketch comedy and good software require the same ingredients:
A cross-disciplinary team of people who see the world in divergent ways.
The willingness to be vulnerable and offer ideas to the team that might be rejected.
A cadenced iterative structure that aims to achieve a goal whose end state isn’t clear at the outset.
A feedback mechanism that sends messages that the team is on the right track. In comedy, that mechanism is laughter. In software, that mechanism has to be coded into each feature.
Q: What do you hope readers take away from the book?
A: I hope readers realize that software is a creative endeavor, not a black-and-white, ones-and-zeroes activity. It helps to know that because it changes the way we interact with software development teams.
If we recognize that they’re crafting a work of art, we tend to give them the space to play and discover. If we don’t, we tend to box them into constraints that degrade the quality of the product.
Q: What are you working on now?
A: At Sketch Development, we’re helping companies figure out how to build faster and smarter—especially in a world where AI is changing the rules.
I believe the concepts in the book will become more applicable as people become more comfortable with AI tools: the feedback loop is speeding up, and the cost of experimentation is decreasing. How do you keep product development from speeding off into chaos in that world?
I’m also working on some talks and workshops that dig deeper into the themes from the book. And because I apparently hate free time, I’m exploring what this all means for leadership teams trying to scale their organizations without losing their soul.
Q: Anything else we should know?
A: Only that the best product insights often come from outside the product world. That’s why I wrote this book—not as a “how-to,” but as a “how-it-feels.” If it gets people to think differently about collaboration, creativity, or just makes them giggle a little, I’ll call it a win.
--Interview with Deborah Kalb
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