Bruce Chizen has the kind of unique executive experience that would fill a book of business school case studies.  

As the CEO of Adobe Systems – the company that makes Photoshop, Premiere and more – Bruce mentored his replacement, Shantanu Narayen. He got mentored by the company's co-founder and original CEO, John Warnock. And he often sat across the bargaining table from Apple CEO Steve Jobs. 

I first met Bruce when I was a young reporter in Silicon Valley, nearly 20 years ago now.   

Today, Bruce sits on many boards of directors, most notably the board of Oracle – run by the one and only Larry Ellison. 

At the same time, Bruce is executive chairman at Informatica. Informatica works with businesses to manage the trove of data they store in the cloud. There, he's working with new CEO Anil Chakravarthy on navigating a tricky job. Not only does Chakravarthy have to inspire the rank and file, he's got to develop his lieutenants and manage a board of directors stacked with impatient private equity investors. 

Here are some highlights of the conversation with Bruce and Anil:

Values Aren't Always Obvious

Living in Silicon Valley (as I did for 14 years), you get to hear a lot about the reputations of different companies. Adobe was founded by two friends who were brilliant engineers, and also really nice guys. It developed a kind culture. Apple and Oracle? Let's just say their founders were a little more colorful.

Chizen, who led Adobe and has gotten an up-close look at Oracle and Apple, says there's not a single right way to do it.

"Steve [Jobs] was impossible many times to be around. I remember showing up at meetings with him, and none of his staff would say anything. It would be Steve, and if Steve wanted somebody to talk, he would to them. It was just a different environment. It worked," Chizen says. "The CEO sets the tone of the company, it's their values, they surround themselves with people who complement their value structure and complement their style. And then it works."

Many people think values work only when they're warm and fuzzy. Not necessarily.

The Stretch

Chakravarthy says it was a decade ago when he first realized we wanted to be a CEO. He was an engineering leader at Symantec, and then-CEO John Thompson (now chairman of Microsoft) placed him in a role managing services to see if he could do it. That moment – stretching him outside of his comfort zone – became a defining one.

"Folks like that started to give me confidence to say, sure, you should aspire to that," Chakravarthy says. "That's when I started to say, I should get a variety of different types of experiences. One thing led to another – that's how I ended up at Informatica as chief product officer."

Mentors sometimes push you into uncomfortable situations that give you a fresh take on what you're capable of.

Fortt Knox is a weekly podcast from CNBC anchor Jon Fortt. Previous episodes of the program can be found here.

Originally published on Linkedin Pulse.