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Steve Comstock  (LinkedIn, Twitter) went from simply wanting to be an “uber-engineer” to the role of CIO of CBS Interactive, where he managed the media conglomerate’s entire digital enterprise. After more than eight years with CBS, Steve recently left the company to pursue new opportunities.

On this special two-part episode of IT Visionaries, Steve generously shares all of his experiences working his way up the IT ladder, including how he first got into technology, what it’s like to be in charge of streaming multiple Super Bowls and other major events, the challenges of the role of CIO, the future of digital media and much more.

Key Takeaways:

Tough moments in Steve’s career — (1:30)

Bridging the gap between the digital and analog side of the business at CBS was a challenge. Because people were at such different spots on the maturity curve of the digital revolution, making change happen at any kind of accelerated pace was extremely difficult.

Another challenge is that because of his title, anything that went wrong ultimately was put on Steve’s shoulders. If a system went down, if an application failed, if any problem came up, Steve was on the hook. Figuring out the right way forward is about trial and error, though, so you have to be OK with failing every now and then.

“It’s a maturity curve thing in my mind of both the technology and the people using the technology to understand how to debug and move quicker.”

“A lot of the failures were misreading maturity, because sometimes you want to be at Spot D but really you’re at Spot A and you think you’re at Spot C. It’s like, oh wait, we skipped over B and C but really we needed to do B and C to get the D to do it right.”

“One of the things that’s really cool about the CIO role is you see everything. There’s probably nothing you could throw at me that I haven’t already failed at.”

Understanding the scope of what going digital means to a business — (19:20)

In media, digital is becoming a much bigger piece of that pie than ever before. As the younger generation moves toward digital-only viewing, the digital departments of media companies are going to be responsible for 80% or more of the business. While this is a relatively new phenomenon, Steve knew right away that his role on the digital side of CBS was going to be an important one. And his prediction came true. Today, when analysts do presentations about the business, the majority of their reports focus on the digital side of the business, how the subscriptions are doing and what to do to optimize the digital strategy.

“I could see it a million miles away. Advertising revenue is going to get soft at some point. Subscriptions are going to be solid. …I always really thought in the back of my head that this is the real deal.”

How digital media has changed the way television is made — (23:15)

Because of the advent of things like Netflix, Amazon and on-demand streaming, consumers are in control of what they watch and when. And because of the freedom that streaming-only platforms enjoy, those companies can take more risks, deliver a ton more pilots or show ideas than you can on traditional media, and just wait and see what sticks. Then they can pour resources into that show and take the data from everything else to come up with a strategy for the next round.

The danger here is what Steve calls “content fatigue,” which happens when there are so many options and too many choices that it overwhelms you.

“You have that whole breadth of content now that is so accessible to everyone.”

Employee productivity — (29:15)

Steve explains that employees are always striving to be more efficient. Technology today, such as voice recognition, auto-logging, and other A.I. is making employees more productive than ever, but it’s also allowing them to be more engaged on a human level. When you’re not worried about taking notes and missing action items because you know your voice A.I. is recording it all for you, it frees you up to have a more engaged and active conversation and actually build relationships with the people you’re working with.

As the next generation enters the workforce, there will be even more technology that needs to be integrated into the system, though. So if Snapchat becomes a business tool, there will need to be advances that allow the interactions that happen on that platform to be logged and have that data analyzed in a way it isn’t right now.

One of the responsibilities you have as a leader is making sure that all of your employees have everything they need or want in order to be as productive as possible from the moment they join the company. There shouldn’t have to be a period of time when they are getting used to new systems or applications. Give them the tools they want and will work for them, and then let them do the jobs they were hired to do.

“From a consumer perspective, we want you to be able to watch the show you want to watch when you want to watch it, where you want to watch it, how you want to watch it. I think employee productivity is the same in that employees are striving to find ways to be more efficient. They want to work in the medium they want to work in. Whether it’s Slack, whether that’s texting, whether it’s email, whether it’s directly on the app, they want to get the information they need at their fingertips.”

“My personal belief is that my job is that when you hire that rockstar marketing person, the first thing they do is start marketing, not figuring how to use the expense system. The salesperson should be out there making calls and calling prospects and qualifying prospects right away and have all the tools they need to get their job done, whatever that looks like.”

Steve’s greatest success: “I think my greatest success was I was just learning from failures and really pivoting and moving quickly and transforming the organization to, to really embrace what we need to do next”

For Part One of this interview, click here.

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