The Space Between Curiosity and Structure: Jonathan Tennis on Learning, Leading, and Staying Human
Learning | Leadership | Curiosity

Introduction
Some people build their careers by climbing a single ladder. Others, like Jonathan Tennis, build by following questions. His journey spans technology, leadership, and systems thinking, all underpinned by a fascination with how people and processes fit together. This is a story about staying curious in structured environments and what that means for modern leadership.

Finding a Home in Complexity
From early roles in technical environments to later positions with broader responsibility, Jonathan gravitated toward the messy middle where business goals, human behavior, and technology meet. He learned how often a problem labeled as “technical” actually began with misaligned expectations, missing communication, or unclear ownership. Instead of turning away from that complexity, he leaned into it.

Balancing Rules and Imagination
Jonathan’s work placed him in organizations that valued control, predictability, and compliance. At the same time, his natural instincts pulled him toward exploration and experimentation. Over time, he developed a quiet craft. He learned to respect necessary rules while still asking “What if” and “Why” at the right moments. That balance helped him build trust with conservative stakeholders without letting curiosity die.

Learning as a Way of Leading
One of Jonathan’s core beliefs is that leaders should model the learning they want to see in their teams. That means admitting when they do not know something, asking for help, and actively seeking new perspectives. In his own career, he made a habit of crossing boundaries between disciplines, listening deeply to subject matter experts, and translating insights across domains.

Paying Attention to the Human Layer
Whether the task involved data, systems, or strategy, Jonathan noticed that outcomes often depended on how people felt and how safe they perceived themselves to be. Were they free to speak up. Did they believe their input mattered. He grew increasingly interested in psychological safety, quiet signals in meetings, and the kinds of questions that encourage reflection instead of defensiveness.

Curiosity as a Long Term Practice
Jonathan does not treat curiosity as a trendy slogan. For him it is a discipline. It requires patience, humility, and sometimes the courage to ask questions that might slow things down in the short term in order to prevent larger problems later. Over the years he found that this steady, thoughtful approach built a reputation for reliability and depth, even in environments that did not always celebrate experimentation.

Key Takeaways

• Many technical problems are rooted in human and structural issues, not just tools

• Effective leaders balance respect for constraints with a commitment to ongoing inquiry

• Modeling learning and humility creates permission for teams to do the same

• Psychological safety and careful listening are critical to good decisions

• Curiosity is not a one time spark but a habit that can be practiced across an entire career