Five More Steps with Jason W. Gallo

Transcript

A lot of leaders talk about resilience. Far fewer can explain how to turn resilience into something a whole team can actually use when the pressure is on. Grant McGaugh sits down with Jason Gallo to trace that shift from a “power through it” mindset to authentic leadership built on tools, trust, and empowerment, shaped by Jason’s Brooklyn upbringing and a Grand Canyon moment where the only goal was “five more steps.”

From there, we zoom out to the biggest workplace shift many of us will ever live through: artificial intelligence. Jason lays out why AI will surpass the impact of the internet and cloud, how agentic AI changes the way work gets done, and why trust infrastructure matters as much as technical infrastructure. We talk candidly about the anxiety people feel when new tools show up overnight, the adoption curve that follows every major platform change, and what leaders can do right now with training, communication, and the humility to say, “We don’t have all the answers.”

Jason also shares a practical story from inside Cisco: “corporate camouflage,” the stuffed elephant that gave a room full of executives permission to be heard, and how that kind of vulnerability can unlock real innovation. We dig into mentorship as a “board of directors” (including devil’s advocate mentors), representation in tech, and how Cisco is transforming its ecosystem through the Cisco 360 partner program using co-design with roughly 35,000 partners worldwide. We close with a personal reminder on prostate cancer awareness and prevention.

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