Jason Trujillo: How Constraints and Frameworks Fuel Creative Problem Solving

Jason Trujillo, a transformational leader with a wide range of experiences, joined Jamie Flinchbaugh on the People Solve Problems podcast to share his unconventional path to becoming a transformational leader and his philosophy on structured problem-solving. With a career spanning companies like Stanley Black & Decker, IBM, Intel, and Harley-Davidson, Jason brings a unique perspective shaped by an unexpected beginning—art school.

Jason explained that his engineering studies actually started at the School of the Art Institute of Chicago, where he explored kinetic sculpture and human-machine interaction. This creative foundation became central to how he approaches problems today. He described problem-solving as fundamentally a creative process, always returning to questions like "What am I looking at? What does that mean? What can I do with it?" This artistic lens has stayed with him throughout his career, providing a unique vantage point for tackling complex business challenges.

A key insight Jason shared is his belief in the power of constraints to fuel creativity. He noted that while young artists often rebel against limitations, there's nothing harder than facing a blank canvas with no boundaries. Jason sees direct parallels between art and business problem solving—just as telling someone to "fix the company" is too broad to be actionable, asking an artist to "make something" without constraints can be paralyzing. He emphasized that frameworks, heuristics, and rubrics provide essential guide rails that allow creative thinking to flourish within defined boundaries.

When discussing his role as a transformation leader, Jason acknowledged the need to wear multiple hats depending on the situation. While he sometimes wishes he could simply fix a broken machine on his own, his current work requires shifting between being an accountable owner in executive meetings and a coach helping others develop their problem-solving capabilities. Jason finds the coaching role most rewarding because he gets to watch people learn, develop, and ultimately succeed—though he candidly admitted that winning doesn't happen as often as people assume, which makes success even sweeter.

Jason introduced a particularly helpful concept he calls "altitude" when working with teams. He explained that sometimes people are working on the right problem but viewing it at the wrong level of detail. Engineers, for instance, might get stuck in technical specifics that aren't relevant to the broader business challenge. By helping them adjust their altitude—lifting up to see the bigger picture—Jason can help technical minds engage with problems at a more appropriate scope.

On the topic of ideation and brainstorming, Jason admitted he used to be "triggered" by traditional brainstorming sessions that often devolved into appeasing the loudest voice or rushing to conclusions. Instead, he advocates for structured ideation using frameworks that make clear whether the group is trying to expand possibilities or converge on solutions. Jason stressed the importance of knowing what outcome to expect from an ideation session and preparing accordingly, transforming what could be an aimless discussion into a constructive planning session that leads to concrete action.

Throughout the conversation, Jason emphasized his core principle: don't solve general problems because nobody has a general problem. Success comes from getting specific, using frameworks intentionally, and helping others build their own problem-solving capabilities.

Connect with Jason Trujillo on LinkedIn to learn more about his approach to transformation and operational excellence.