Guy Kawasaki: ‘You Had To Prove Yourself Every Day With Steve Jobs’

Guy Kawasaki, one of Apple’s earliest employees, recalls vividly the day he “passed the Steve Jobs test.” Sitting in his cubicle, Kawasaki was startled when Jobs walked in with an unfamiliar man and asked his opinion on a particular company and product.

“I gave him this whole diatribe,” Kawasaki shared on the podcast. “I said, it’s a mediocre company, mediocre product. It doesn’t really take advantage of the Macintosh graphical user interface. It’s not a strategic product or strategic company for us, Steve.”

Jobs then introduced Kawasaki to the stranger—he was the CEO of that very company. By being bluntly honest, Kawasaki learned he had done exactly what Jobs expected.

“That’s what it was like,” he explained. “You had to prove yourself every day with Steve Jobs.”

This moment taught Kawasaki the value of truth over flattery, especially with a leader as mission-driven as Jobs. “[This CEO] met with Steve, and he told him, ‘Yeah, my company’s doing so well. We’re selling thousands of copies of software every month. We have a revolutionary patent-pending, curve-jumping, and paradigm-shifting educational software.’ And Steve would have said, ‘No, you’re full of shit. Your product is shit.’ If I had said it was great, and Steve thought it was shit, I might have been fired on the spot. So I passed the Steve Jobs test that day, and I lived to work another day,” Kawasaki recalled.

He didn’t just work another day—Kawasaki went on to play a major role in Apple’s legendary launch of the Macintosh in 1984. As Chief Evangelist at Apple, and now in the same role at Canva, he’s dedicated his career to promoting products that genuinely impact people’s lives.

In our conversation, Kawasaki reflected on how Jobs’ unwavering mission-driven approach taught him to push aside style and focus on impact. “Steve Jobs was on this mission to create the world’s greatest computer, and if you were incompetent, or even just kind of so-so, he had very little tolerance for that.”

In this episode, Kawasaki dives deep into the leadership lessons he’s applied throughout his career, including:

• The key differences between mission-driven and ego-driven leaders.
• The contrast between Chief Marketing Officers (CMOs) and Chief Evangelist Officers (CEOs).
• Why he’s committed to lifelong learning, from picking up hockey at 44 to surfing at 60.

Kawasaki also compared working for Jobs to playing for some of the toughest coaches in sports. “Working for Steve Jobs is probably like playing for Bobby Knight or Vince Lombardi,” he said. “They demanded perfection, but if you were part of the team, you loved them.”