As he was once called the most experienced CIO in the world, Mark Settle (formerly of Okta and author of the book Truth from the Trenches: A Practical Guide to the Art of IT Management) may know a thing or two about what it takes to occupy the role. Outside of being in charge of IT strategy and the systems required to support the organization’s objectives and goals, Settle says every CIO depends on their business systems teams to “create the perceptions around the credibility and competence of the IT organization” due to their constant socialization with both executives and stakeholders to ensure that the business goals surrounding technology are met. It is because of this socialization that IT (whom Systems leaders work parallel with) can focus on building an infrastructure surrounding connectivity, security and operational efficiency – one department cannot exist without the other, or else, they’re bogged down.

Having inhabited some Systems roles (before “business systems” had a name) prior to becoming a CIO, Settle makes a great candidate for narrating the journey. In our new series How to Become a CIO, current and former executives like Settle will share insights from positions before obtaining their biggest roles, things they wish they’d learned, different resources that helped them along the way, and steps you can take if you’re currently a Systems leader wishing to ascend to C-suite. Both challenges and opportunities, pain points and possible resolutions will be addressed in this series, all with the aim of helping people with a Business Technology mindset grow to oversee those strategies at companies in the future.        

In our sitdown, the 7-time CIO shares how he began tackling project management as a director at a research lab, as well as visualization technology, database systems, and other new tech in the years that followed. While he’s always had a love for technology, the path wasn’t always clear for him.

The Evolution of a CIO 

What sort of roles did you take before becoming a CIO and why did that trajectory make sense at the time?

When I left college, I didn’t even know what a CIO was and like I always tell people, ‘Nobody goes to college to become a CIO.’ So I came up through the ranks. I went to a research lab where a lot of technology was involved and I was a director/project manager for some big projects. Those are where I cut my teeth in management and one thing led to another. I also worked at an oil and gas company for 10 years with a lot of technology focused on oil and gas. I was in the exploration and production division, so we made extensive use of computers and visualization technologies and database systems. We processed seismic data, so a lot of the daily activities were computer-mediated. I also did a 4-year stint at NASA as a program scientist. It was almost like getting a master’s degree in computer science with experiential learning, so a lot came from that. 

That’s certainly an illustrious start. In your experience across 7 CIO roles, how has the role of a CIO and the roles of those who report to them changed? Is it mostly job duties that have changed? Have team dynamics changed? What’s your take on that?

It depends on the situation. Every company may divide those things up a little differently, but almost every IT group has got sort of applications team and an infrastructure team. Sometimes there’s a separate team for customer-facing websites, that’s a whole other line of business with its own technologies. 

Prepping for a CIO Role

When you think about entering the role, are there certain things people should look out for, or expertise they should have prior?

So actually, starting with small projects is a good thing because you get to test your sea legs and figure out how this system or process actually works and what your role is from these different perspectives. Let’s say you are a team lead, then you’re a manager, senior manager, director, senior director, VP, etc. Even though you may not formally be a project manager, you still have a leadership role around almost every major initiative that’s going on within the organization.

For example, you could be a senior director on the applications team and let’s say, you came up through NetSuite and that was your sweet spot. Well, there could be a major overhaul going on in the Workday platform or maybe your marketing automation platform is being replaced with something else. Still, your experience in NetSuite and projects in NetSuite give you the ability to ask a lot of the right questions about what your team is doing in that other project.

But after a while, your experience reaches a point where you can make a lot of decisions pretty intuitively and that’s something I remember, in my own career – realizing that I just didn’t need to waste a lot of organizational time on certain things because I could just see that the way we’re doing it today is wrong and needs to be course corrected.

Breaking Down the Roles of a CIO 

At Biz Systems Magic, you talk about project management and how that plays a big part in a CIO’s role. Can you talk a little bit more about that?

I think practical experience is incredibly important around project management. You can get certified through PMI: Project Management Institute. That’s not a bad thing to do, but I’ve also seen people that have the certification but don’t have the aptitude for the role.

The really good leaders align the team around clear objectives, impart a sense of urgency, and set an example to everyone else with their organizational skills, dedication, and enthusiasm for the project.

I wanted to switch to IT governance and risk management. That, of course, also plays a factor, but how much would you say prior experience plays when it comes to those areas in a CIO role?

There is no one-size-fits-all governance model or framework for IT because something that works in one company may not work for another. What influences it is the personalities of the executives that are going to take part in the oversight. So you have to be very conscious of staying within what’s possible within your company so it’s useful. You’ve got to have a real sense of purpose of why we put this group together. You’ve got to try to keep the meetings short and engagement at the highest possible level, and as you build trust over time, it should become simpler, take less time and involve fewer people.

So you really have to see the value in IT governance for your organization or it can become too big of an undertaking where you may lose sight of the goal?

Yes, and really one of the first things you have to do is ask yourself, ‘Is this an investment committee, where we’re trying to spend money, or is this an information-sharing committee, where you want to socialize information about what’s going on in IT?’ Because we can do either one, but let’s not fool ourselves as to why we are here at the end of the day.

We talked a bit about project management and other skills that are more technical. Do you think there’s a really important skill a CIO should have that’s not technical?

Vendor management is very important, right, because your vendors are very important. A lot of your cost issues are going to revolve around your vendors and it’s not just software and hardware – you’re going to have service vendors as well. So those are pretty strategic relationships to have. The more insight you have on your vendors and their objectives, the better you’ll be at handling those relationships and making decisions accordingly.

CIO Best Practices to Follow

Did you find any particular resources useful as you were going up the ladder? 

The best relationships with bosses, for me, were ones where they really kept pushing more responsibilities on me at the time. What was really important was keeping so busy that I had a lot of freedom of action to try to take on as much as I could.

In my new book called Truth from the Valley, I talk about how there’s never enough people or hours in the day to do everything. So one of the things you need continually ask yourself is whether you are performing duties or activities that could be easily shared or delegated to others. 

Be very conscious of things that you should stop doing and things you should try to get rid of. I think that’s a hard thing for people to do. They want to do everything they did before and they’ll take on every new opportunity that shows up.

There’s a great Steve Job’s quote that says, ‘It doesn’t make sense to hire smart people and tell them what to do; we hire smart people so they can tell us what to do.’ Embody that.

A Note to Future CIOs 

Is there any final advice you’d give someone hoping to become a CIO one day, whether they’re coming from a business systems background or just overall?

Every employee should conduct an annual performance review on their own time and ask themselves three questions regarding their technical, business, and people management experience: 

  1. Was my technical knowledge, skills or expertise enhanced in some way?
  2. Did I work on some business problems where I obtained more insight into how our business actually works, or how we make money? 
  3. Was I put into situations where I had to manage virtual teams, international teams, or get contractors to work productively with full-time employees?

IT professionals tend to prioritize their technical knowledge very high, but over the course of a career, those other two dimensions, your business knowledge and people management skills, become increasingly important. You can’t be the head of IT without managing people that do the work.

Alongside that, be prepared. Advancement only happens when hard work and preparation meet opportunity, and you can only control the former two. You’ve got to proactively start managing your career and searching for other opportunities if none present themselves. 

For aspiring CIOs, track how you’re investing your time in activities that will help you reach your goal. Be very conscious of where your comfort zone is, and don’t be afraid to break boundaries. No one wants a scared or timid CIO.

Learn more about Settle and his thoughts on IT management at CIO.com.

Stay tuned for our upcoming CIO newsletter on information and technology trends in 2020 and beyond. Request to Join Our Community to learn how Systems leaders and CIOs build successful relationships.

Pamela Seaton
About Pamela Seaton

Pamela is a journalist and technology enthusiast writing for the growing business systems community.