From SNL to software

John Krewson is the founder and CEO of Sketch Development Services, a St. Louis-based consultancy known for helping companies simplify the complex process of delivering software. With a background that spans software development, project management, and leadership, plus a surprising past in entertainment, including a brief appearance on Saturday Night Live, Krewson brings a unique perspective to the world of product development. He’s the author of Pitch, Sketch, Launch: What Sketch Comedy Can Teach Us About Product Development, where he draws parallels between the fast-paced, iterative world of sketch comedy and the demands of modern software teams.

From SNL to software: Tech CEO on what Sketch Comedy can teach us about product development

Below, Krewson shares how principles like experimentation, feedback, adaptability, and even humor can help engineering teams break out of rigid routines and rediscover their creative energy. His focus is on helping leaders balance innovation with execution, navigate the challenges of human-AI collaboration, and avoid the traps of “feature factory” culture. In this Q&A, Krewson also offers fresh insights into how companies can build environments where bold ideas thrive and teams stay nimble in an ever-changing landscape.

ADM: You’ve talked about using sketch comedy as a model for software development, can you unpack how this approach translates into concrete practices that developers can adopt in their day-to-day coding or team rituals?

Krewson: It comes down to empirical process control, favoring transparency, inspection, and adaptability over rigid project management. Give your people room to not shine, to be creative and try new things. Then make sure they’re coming up for air and getting feedback on a regular schedule. This makes it safe for your employees (and the organization) to try new things, because you can correct course often. This is a lot like the way SNL produces a new television show every single week during the season.

ADM: Engineering teams often struggle with burnout and “feature factory” syndrome. How can leaders create a culture where developers feel inspired and empowered to innovate?

Krewson: The “factory” analogy is right on the money in my opinion. Assembly lines are great for products that are complicated, but not complex. For example, an airplane is complicated because it has lots of parts, but it’s not complex because putting the same parts in the same places in the same order will get you the same outcome every time. Software development is extremely complex, which means you have to accept, even embrace, the fact that there will be false starts and missteps on the way to your goal. If you can’t navigate VUCA (volatility, uncertainty, complexity, and ambiguity) with confidence, you’re not ready to lead a software team.

ADM: Many developers miss the early, scrappy energy of startup environments. How can principles from sketch comedy help recapture that spirit, even in mature engineering teams?

Krewson: It’s funny because startups seem to fall into good habits naturally. Then, as companies grow, it’s like they forget how to operate. They turn into those feature factories. You can recapture that bold energy by operating more like SNL. Every sprint (a week at SNL, two weeks for us at Sketch) is a fresh start. You examine all types of ideas: good, bad, and ugly, with an open mind and a willingness to give and receive tough feedback. The top ideas get sketched out (a script at SNL, a POC or MVP in software). The very best ideas go into production (airing in the live show at SNL, or becoming enterprise software for us and our clients). Everything else is eliminated.

ADM: With AI becoming a core part of modern development workflows, how does your team dynamic model adapt to hybrid human-AI collaboration?

Krewson: This hasn’t felt like a big transformation for us, just the natural next step in a state of constant evolution. We built this company on our ability to help human teams build better software together. Now we’re helping them make AI part of the team, and part of the software. We’re not panicking about the “human vs. AI” debate because we see how productive humans and AI can be together. Trying to “vibe code” an enterprise app is begging for a data breach and poor scalability. We need smart humans to design systems the right way, and AI is helpful when it's time to do some of the rote tasks (with oversight).

ADM: You draw parallels between product managers and showrunners. What can engineering leads and senior developers learn from showrunning when it comes to guiding product vision and technical execution?

Krewson: A showrunner is responsible for providing a lot of the driving force behind a TV show. They’re stewards of both the creative vision and have a lot of say in what makes it to air. But they’re not often the ones writing the scripts, and they’re not in front of the camera. They affect what the show will look like, but they have to trust the cast to execute (and remove obstacles as needed). The best product leaders are like that, too. They set the direction, provide feedback, and remove obstacles without micromanaging the details.

ADM: Collaboration breakdowns are a major pain point for dev teams. How can sketch comedy’s iterative, “yes, and” mindset reshape how cross-functional product teams design and ship software?

Krewson: Bad collaboration happens for a lot of reasons, and a big one is that people are forced into roles or onto tasks that don’t suit them. When teams are allowed to self-organize around a shared goal or problem, collaboration comes much more naturally. A leader’s job is to assemble the team and point them toward the desired outcome, without assigning specific tasks to specific people. Now you’ve enabled a “yes, and” mindset because everyone contributes to the effort in a way that aligns with their strengths and interests, rather than being forced into a rigid way of doing things and arguing over what that way should be. It should be pointed out that “yes, and” is a principle from the world of improvisation. While related, it’s not the same as sketch comedy. Think of sketch comedy as polished iterations of improvised comedy. The “yes, and” was the spark of innovation; the iteration makes it industrial grade.

ADM: Software used to be a hotbed of creative experimentation. Why do you think some of today’s most innovative companies are losing that edge, and what can developers do to reverse this trend?

Krewson: Again, it’s because they become feature factories, trying to gold plate their existing success. They have more to lose, so they try to protect that with a “that’s how we’ve always done it” mindset. Building great software takes a sort of wild west bravado, though, and you can’t have that when you’re playing not to lose. When it no longer feels safe to try new things that will sometimes fail, you’re about to get passed by the bolder, faster competitor.

ADM: You’ve warned about the dark side of “efficiency obsession.” How can teams strike a balance between optimizing processes and preserving space for creative problem-solving?

Krewson: Efficiency is all about doing something faster and with fewer resources. But building the wrong thing at high speed will only take you further away from where you want to be. SNL’s process is objectively very inefficient, but it’s extremely productive. You can optimize for productivity over efficiency by focusing on delivering value in smaller increments but on a more regular basis. That leaves room for experimentation without slowing you down.

ADM: The term “transformation constipation” is intriguing. Can you explain what it looks like from a developer’s perspective, and how engineering teams can “unblock” themselves to stay nimble?

Krewson: Signs of transformation constipation include organizational irritability, finger pointing, an annoyance with repeated “transformations,” and a search for a magic elixir that will fix everything. You can prevent this if you stop chasing a series of huge transformations and adopt a mindset of constant evolution. This allows you to make small, tolerable changes without getting overwhelmed by a massive scope. Start small by looking for an easy way to make a positive impact, even if the positive outcome is also small. This gives the team energy to tackle the next change, which yields another improvement, and so on.

About John Krewson

John Krewson is the founder and CEO of Sketch Development Services, a St. Louis based consultancy that focuses on helping companies simplify the complex process of delivering software. Founded in 2015, Sketch is a two-time member of the Inc 5000. Sketch has worked with dozens of companies from startups to the Fortune 50 to help them learn, adopt, and apply new ways of working to match an ever-changing work environment. 

Prior to establishing Sketch, John's career path encompassed various roles, including software developer, project manager, technology leader, and consultant. In addition to his professional endeavors, John has a unique past in the entertainment industry. In 1997, he made a brief appearance on Saturday Night Live. He is also author of Pitch, Sketch, Launch: What Sketch Comedy Can Teach Us About Product Development.