Leadership, AI, and Building High-Performing Teams with Rich Cannon

What does it really take to build genuinely connected teams in today's technology-driven world? Rich Cannon brings extraordinary perspective as someone who's lived in all three worlds of business leadership—founder, senior executive at Microsoft, and "hired gun" CEO.

The revelation at the heart of this conversation might surprise you: despite all our technological advancement, the fundamental challenge facing organizations today is human disconnection. "People really are disconnected at the senior levels of many companies," Rich explains, "which impacts people's ability to change together." In a refreshingly honest moment, he shares how being identified as "the highest ranking yellow energy person" at Microsoft brought him to tears, validating his struggle of leading with relational energy in an environment that prized different qualities.

Rich takes us through his practical approach to transforming team dynamics, starting with self-awareness and creating shared language through personality assessment tools like Insights Discovery. Unlike conventional wisdom that minimizes conflict, Rich advocates for healthy confrontation: "Conflict in a team is healthy," he asserts, explaining how constructive tension ultimately creates stronger connections when teams work through it together.

Perhaps most compelling is Rich's counter-intuitive perspective on remote teambuilding. Having transformed an entire company culture during COVID without meeting his team for five months, he firmly believes connection doesn't require physical presence—it requires intentionality and the right framework. His formula? Combine growth mindset with connected mindset: "We first, me second."

Looking toward our AI-driven future, Rich offers an optimistic view that technology can actually enhance rather than diminish our humanity. Connect with Rich on LinkedIn to continue the conversation about creating more connected, high-performing teams in your organization.