John's unconventional career path

Summary

In this episode, Andy talks with John Krewson, co-author of Pitch, Sketch, Launch: A Sketch Comedy Approach to Product Development. John's journey spans software development, acting, and even a stint with Saturday Night Live. He now leads Sketch Development, where he helps teams build products people actually want, faster and with more joy.

In this conversation, John explains why project teams should behave more like creative troupes than traditional org charts. You'll hear how laughter can be a feedback loop, why messy first drafts matter, and how simple tools like sticky notes, Elmo cards, and Lean Coffee can radically improve your team's collaboration. We also explore how sketch comedy's "test before polish" approach can transform how we ship ideas, and what that looks like on real-world teams.

From unblocking meetings to unleashing creativity, this episode is packed with practical tools and paradigm shifts. If you're looking to bring more energy, experimentation, and feedback into your team's workflow, this episode is for you!

Sound Bites

• "The best ideas often start as bad ones. The magic is in iteration."
• "You're not building a product. You're testing a hypothesis in the real world."
• "Sketch comedy taught me this: if the audience isn't laughing, it doesn't work. Product teams need that same feedback mindset."
• "You can't argue with the emotion of a dead silent audience when you think you've got gold."
• "We often equate busy with productive. But they're not the same thing."
• "A meeting isn't productive just because everyone showed up. Did it move ideas forward?"
• "Troupes thrive on trust and feedback. Traditional teams often operate on fear and approval."
• "I was a mediocre software developer, which made me well-suited for management."
• "You are sucking the fun out of this. We are building software here. We get to play on computers. Let's make this fun."
• "There's this ruthless search for feedback that we learn how not to take things personally."
• "Nowhere in that iron triangle does anybody talk about whether or not the customer said, 'I needed that thing in the first place.'"
• "We're not just cross-functional. We're cross-committed. That's what makes a team operate like a troupe."
• "If you're building something new, you need a mechanism to decide if it's valuable. And if it isn't, you toss it."
• "The law of averages will tell you: 80% of the ideas need to be tossed."

Chapters

• 00:00 Introduction
• 01:46 Start of Interview
• 01:57 Career Backstory
• 07:30 Acting Skills in Daily Work
• 12:00 Busy vs Productive
• 14:07 Project vs Product
• 17:20 Teams as Troupes
• 22:13 Meeting Tools and Techniques
• 27:37 Laugh Testability
• 33:35 Creative Mindsets at Work
• 35:21 Co-Authoring and Collaboration
• 38:00 Applying Ideas at Home
• 40:33 End of Interview
• 41:05 Andy Comments After the Interview
• 44:13 Outtakes

Learn More

You can learn more about John and the book at SketchDev.io/pitch-sketch-launch.

For more learning on this topic, check out:

• Episode 316 with Jennifer Aaker and Naomi Bagdonas. It's a conversation on humor as a secret weapon in business and life.
• Episode 109 with Peter McGraw. It's also about humor, a fun follow-up, even though John's book isn't just about comedy.
• Episode 469 with Phil Wilson. It's packed with great ideas for unleashing your team, which ties in beautifully with John's approach.

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Talent Triangle: Power Skills

Topics: Creativity, Feedback Loops, Team Collaboration, Agile Thinking, Innovation, Leadership, Project Management, Development, Meetings, Humor, Iteration, Trust, Team Culture, Psychological Safety, Growth Mindset

The following music was used for this episode:

Music: Tuesday by Sascha Ende License (CC BY 4.0): https://filmmusic.io/standard-license

Music: Brooklyn Nights by Tim Kulig License (CC BY 4.0): https://filmmusic.io/standard-license