Pitch, Sketch, Launch Your Team’s Creativity with John Krewson and Rob Kutner

Leaders know that keeping a team innovative is easier said than done. The pressure to deliver results, stick to timelines, and avoid mistakes can stifle the very creativity that sparks breakthrough ideas. But what if leaders could borrow a proven process from one of the most successful creative teams in entertainment history?

In a recent episode of The Leadership Habit Podcast, Rob Kutner and John Krewson shared how the Saturday Night Live (SNL) approach to creating sketches can inspire leaders to spark creativity, embrace iteration, and launch winning ideas.

Meet John Krewson and Rob Kutner

John Krewson is the founder and CEO of Sketch Development Services, a two-time member of the Inc. 5000 list, and a former comedian who even appeared on an episode of SNL in 1997. With a background in both entertainment and software development, John has a unique perspective on how to blend creativity and business strategy.

Rob Kutner is an award-winning comedy writer for The Daily Show with Jon Stewart, Conan, and more. For the past six years, he has taught sketch comedy writing at Loyola Marymount University’s School of Film and Television. Together, John and Rob co-authored Pitch, Sketch, Launch, a book that applies the principles of sketch comedy to team innovation.

1. Start with a Flood of Ideas

On SNL, the week kicks off with a high-energy pitch session where anything goes. As John described, “This is a no-holds-barred, no ideas are bad ideas brainstorming session.” Around 100 ideas are generated, knowing that only a handful will make it to air.

Leaders can use this approach by creating safe spaces for idea generation where quantity comes before quality. Removing judgment in the early stages gives your team the freedom to think bigger.

Try this: Schedule a weekly 30-minute “idea jam” with no evaluation—just contribution.

2. Iterate Quickly and Often

John emphasized that creativity is rarely instant perfection: “The best solutions do not emerge fully formed from the thigh of a great leader.” Instead, they’re the product of steady, incremental improvement.

In business, this is an essential creative leadership strategy. Keep projects small and self-contained so you can evaluate, adjust, and move forward without being bogged down by weeks of sunk effort.

Try this: Break projects into two-week sprints with a review session at the end of each cycle.

3. Create the Freedom to Fail

Rob pointed out that in comedy, mistakes are part of the process: “Freedom to make bad pitches” is a core value. Even seasoned professionals start with “not this, but something like it” ideas to spark the right solution.

For leaders, encouraging failure in early stages prevents fear from killing creativity. Make it clear that less-than-perfect ideas are stepping stones to the winning concept.

Try this: Reward contributions to the process, not just final results. Publicly acknowledge when a “bad” idea inspired a breakthrough.

4. Keep the Boss Out—At First

Reflecting on his own career, Rob shared that hierarchy can unintentionally stifle creativity: “We couldn’t really pitch when Conan was in the room.” Even with a supportive leader, the pressure to impress can limit bold thinking.

Leaders should step back in the early creative phases, then rejoin when ideas are ready for refinement and alignment with business goals.

Try this: Assign a peer facilitator for brainstorming sessions and review ideas as a group later.

5. Stay Anchored to End-User Value

Rob also stressed the importance of keeping the audience—or in business, the end user—front and center: “Is this enhancing the desired end user value?” On SNL, the metric is simple: did it make people laugh? In business, your “laugh” is the value your customer receives.

Try this: Define your team’s “end-user value” and revisit it during every project review.

Where to Find More From John and Rob

You can connect with John Krewson on LinkedIn, or learn more about John’s work at sketchdev.io and find Pitch, Sketch, Launch on Amazon in print, e-book, and audiobook formats. In the audiobook, you’ll hear sketches performed by a comedy team—bringing their concepts to life in a fun and memorable way. Rob can be found on LinkedIn and at robkutner.com, where he shares his comedy and writing projects.

Bring More Creativity to Your Leadership

Crestcom’s leadership training programs are designed to help leaders apply practical strategies—like the ones shared here—to inspire innovation, strengthen teams, and achieve results. In our interactive workshops, you’ll learn proven techniques to foster leadership and creativity, build trust, and adapt quickly to change. Discover how you and your team can unlock your creative potential—request a complimentary leadership skills workshop today.

 

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