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Technology Executives Share Advice for Up And Coming CIOs

As the role of the CIO shifts towards the core of the business, technology thought-leaders share their best words of advice for new and aspiring CIOs.
Catherine Pyle
Contributing Writer

Leadership opportunities come with a progression of new responsibilities at every level on the career ladder, and the top spot is no different. As CIOs become more and more integral to the core of business, up-and-comers are turning to seasoned executives for advice to weather the chaos on their professional journey.

The National CIO Review asked industry-leading technology executives at the top of their game to provide advice to aspiring technology leaders on their path to the CIO suite.

Karen Bird, CIO at Hooters of America (Retired)

It’s important to build strong relationships between your peer group and even outside your organization. Honestly, if you want a CIO role, then go out and get it. It’s also important to prepare yourself with the business side of operations. I often refer to my accounting days, and that experience helps me even now. Leaders need to be able to prepare business plans and know how to construct a proposal. A CIO needs to learn a little of everything to do this job well.

Marcus Wasdin, Chief Information Officer at Atlanta Hawks (Former)

My first item of advice – and this is for any business professional – is you’ve got to be curious. Think about how things work and how constituent pieces work together to make your overall business successful. Don’t get into this business unless you are curious about how things work.

My second item of advice is to try to be well-rounded. As you’ve heard, my path to the CIO position was a little bit different. I didn’t start in an IT shop. I started my path as a consultant and more in sales, albeit at a technology company, and then kind of worked my way back into tech. Try to get some external experiences outside of technology to round you out a little bit better. Understand how the finance and accounting part of your organization works. Understand how the sales part of your organization works and how the marketing parts of your organization work, because every single part of the business now is touched in some shape, form, or fashion by technology or data. The more you can understand those different aspects of the business, the better off you’ll be.

My third item of advice would just be to be fired up about it. Do something that you’re excited about.

Michael McCalmont, Vice President of IT at AtriCure

Always take the difficult assignments when offered. You’ll learn something as a result of it. Aspiring CIOs should also be curious about technology and its applications. Good leaders learn how to translate technology into business-friendly terms because that’s the key to influencing people and leadership. It’s also important to build a high-performing team: you’re only as good as your people. Lastly, I would say try to be diverse in your technical background so that you can understand as much as possible about your profession.

Mike Nettles, Chief Digital and Technology Officer at Zaxby’s

First and foremost, recognize that today’s world is not just about technology, but in being a trusted adviser to senior management. For example, you have to fully understand the operation you are trying to support and get involved in cross-functional activities before preaching from the technology side.

Most businesses will value you even more if you have practical observational skills across all functions, including operational, legal, and supply-chain processes.

Jodi Eddy, Chief Information and Digital Officer at Boston Scientific

First, I would say only strive to be a CIO if you love the field as it requires a lot of effort, dedication and trade-offs.   Next, developing people skills are as important as technical skills.  You have to gain the respect of others and surround yourself with smart and dedicated people.  A strong team is essential to success.

Dennis Yang, Chief Information Officer at Motion Picture Association

First, think like a businessperson and learn about the business. Your C-level peers really don’t care about things like AWS, Google, or Azure, they are more focused on the business outcomes. They rely on you to help them make decisions about software. Secondly, it’s important to put yourself in their shoes to understand the situation and make the best possible recommendation for a solution or outcome. Technical skill is the foundation, you have to know about computers and IT and security, but I think people skills are much more important.

Gene Berry, Chief Information Officer at OneAmerica (Former)

I think it is critical for today’s CIO to be less of a technologist and more of a business strategist. During my early years in IT, there was more focus on technology and less focus on business. Today, the CIO must know where the business is heading and figure out ways to create the capabilities they require.

What you are going to see, and it’s already happening, is that CIOs are starting to become chief digital officers and chief data officers. Companies are amassing huge amounts of data but the key to success is figuring out how to manage the data securely and use it for real-time decision-making.

Phil Crawford, Chief Technology Officer at CKE Restaurants

First and foremost, be humble and always remember your roots and where you come from. Second, continue to educate yourself outside of traditional schooling.  Keep up with trends. Read. Go to seminars. Never stop learning. Finally, remember that is ok to fail as long as you learn from it and don’t make the same mistakes again. 

Dave Roberts, Chief Information Officer at CiCis

Don’t be afraid to reach out to somebody who has been there and done that. Try to get some of their time. People are a lot more open to giving you feedback than you might think. I was in that seat before. The other thing I’d say is to maintain a level of humility within your role. No matter how good you are, you can always challenge yourself to be better. There will always be new challenges and you’ve got to be able to step up to that. As I started to become a leader in technology, that drive never left me.

Secondly, there are a lot more networking opportunities due to LinkedIn, SEO professionals, and partner networks like the CIO Professional Network. These groups are now more prevalent and mainstream versus how they may have just met at a coffee shop 10 years ago. These things are so important to the overall growth of the technology sector, especially because things change so rapidly. I’m having the chance to tell my story here and I wouldn’t have had that opportunity if I had not become a part of the CIO Professional Network.

Kevin Blanchard, Chief Information Officer at SVP Worldwide

Think about why you want to be a CIO. Identify and secure a senior technology mentor. Put yourself out there in terms of tackling challenging initiatives and opportunities. Push yourself to continually learn via academic programs, technical training, and personal study. Do what you must to remain current, technically and operationally.

Importantly, don’t be afraid to fail. And when you do, pick yourself up and identify the learning opportunities. Keep pushing because the CIO seat can one day be yours.

Tim Ryan, Chief Information Officer at Aegis Sciences Corporation

People often have the perception that to grow your career, you need to be promoted to achieve that growth. Sometimes taking on new roles exposes us to new technologies and new businesses. Even if it’s a lateral move or a step backward from a job title perspective, it will actually give you more learnings, increasing your opportunities going forward. Sometimes you must take a step back. Speaking from my own experience, taking on new roles has exposed me to new opportunities and enabled me to grow more rapidly. I think that’s hard for some people to understand, but I do think that’s a key to learning.

Bill Fortwangler, Chief Information Officer at Dollar Bank

I say this to those who I mentor: “Do you really want this?” I say this to my successors as well. It is constant stress and constant problem-solving. There’s rarely a day when everything’s just great. As CIO I still may be on an overnight call to ensure our services are available to our customers.

As CIO, you will have to interact with people and win over their confidence at every level. There’s always someone who isn’t going to be in your court. And when something goes wrong, you’re going to have to explain, in layman’s terms, why it happened on your watch.

With that said, this job can be very rewarding, especially when so many people come together and resolve a problem. You’ve got to be able to talk to anyone in the organization. Everyone needs to have the opportunity to complain. You’ve got to be approachable. You are being watched constantly, from above and below, and everything you do is analyzed. But, most importantly, you’ve got to protect your people. Even as more automations are put in place, you still need skilled, talented, intelligent people.

Dave Finnegan, Chief Information Officer at Orvis (Former)

There is a big distinction between being a lifelong learner and a lifelong knower. The learners are constantly evolving, and that’s definitely required for seasoned and innovative executives. Everyone has soft spots, but lifelong learners have the ability to deal outside of their comfort zones and have greater potential.

Scott Checkoway, Chief Information Office at onehome

Understand your audience. Whether it is an internal team member or an external customer it’s vital to understand your audience to provide the best experience possible. When I think about providing that experience, I think of it as medical professionals that treat patients. I consider that person my loved one, thinking about how I would guarantee they are provided the best quality care.

Connecting with the people in your department and being able to relate to them is very important. Especially making sure you have the knowledge base to understand how to relate to them and ask the right questions. That doesn’t mean that you must have been a developer or engineer so long as you understand how their work connects the technology to the business puzzle that needs to be solved.

Calvin Rhodes, Chief Information Officer at State of Georgia (Former)

Timing is everything. This is a great time to have an interest in the many different areas associated with IT. Corporations have a much greater interest in this field, so it’s a great time to look in this direction for a career. Individually, and I think this is true for all of life, you have to be a trusted source of information. I appreciate people who honestly tell me when they don’t know an answer. When you lose someone’s trust, it’s very hard to get it back.

You also need to keep the big picture in view. Participate in meetings, take the big goals of an organization, and make sure the role that IT plays supports these goals and objectives. If you only focus on your individual tasks, that’s not what senior leadership is looking for. We’re in a great position to turn data into information, so if you turn that information into business strategies you will become indispensable. These are the skills people are looking for in a CIO. The biggest part of this advice is to be trustworthy. It’s very hard to gain trust back.

John Lukas, Chief Information Officer at RaceTrac

I have had up to six individuals that have worked next to me, with me, and for me in my organizations that are now leading organizations. They are either CIOs, VPs, or SVPs, and I am very proud of that. A common trait across all of them is that they intimately understood how we made revenue, how to improve our revenue, where we can impact operational processes and costs, and the importance of applying technology to partner with business leaders.

It didn’t matter whether it was helping the chief legal officer put an efficient lease management system in place or helping cut $7 million of inventory variance out of a recipe management system. In both of those cases, you must have a passion for learning each of the department disciplines so that you can bring the right consulting and advancements to their piece of the organization.

Don Zimmerman, Chief Information Officer at Landry’s

Get a well-rounded set of experiences. Fill in that portrait. Frito Lay really shaped my philosophy and I always share it with the team when I get into a new role. I tell them that they paint their own portrait. If you only do one thing and you keep painting it over and over again, that’s fine, but the portrait isn’t complete. How much of it can you complete over the course of time, or a stint at a company, or even a stint in a role? Flesh it out! As you do that, you build out a complete person, a professional, a portrait. You are better and stronger for the next thing you do.

Don’t fall into the trap of cookie-cutter thinking, meaning “A CIO just looks like this.” There can and should be a lot of variation and diversity – it makes things stronger. The more diverse your experience set, the more prepared you are for that leadership position. Because one thing about leadership: you don’t know what is going to come next.

Priya Serai, Chief Information Officer at Zeus Fire and Security

I feel like to be a successful CIO, you need to differentiate from your competition. Learn to understand what the customer really wants, and then match it with the right technology solution.

I remember this Henry Ford quote. He said, “If I had asked people what they wanted, they would have said faster horses.” Don’t stop to do simply what others tell you to do. Think beyond that and don’t accept the status quo.

Jamie Adams, Chief Information Officer at Lifeway Christian

I would tell them that, if CIO is the path that they want to travel, then they have to be willing to embrace and enjoy change, evolve with the role and with the ever-changing technology landscape, and learn to be a great salesperson. You’ll be working with and accountable to business leaders, each of whom thinks that their initiative is the most important. As a CIO you have to take all of these different initiatives and help them see the ones that truly are the most important – and do it with a smile.

One of the reasons that I enjoyed MIS as a major was because it teaches you how to utilize technology to help a company achieve higher business results. If you’re looking to become a CIO, then you’re going to have to attain business and technical skills – through degrees or an advanced degree, for example – and merge the two so that you have the best of both worlds.

Lisa McVey, Chief Information Officer at National Christian Foundation

I think it boils down to being relational. They need to know how to work not only across their peer group but with others, like the legal counsel, operating officers, and CFOs. They need to know how to translate technology into business terms and values, and all of these require good relationships. They must also have that sense of the end customer, whether it’s internal or external. So, when we talk about staying ahead of trends, it’s not just technology trends. It’s the industry they’re in, the industry trends and what’s going on in the competitive landscape. They need to look at it holistically.

To learn these skills and the relational aspects involved, they need coaching and mentoring – observing someone who has those skillsets. If you give them the opportunity to get out of their comfort zone, mentor them and align them with somebody who has come up in that way successfully, those soft skills will be established. For example, I’m currently working with someone who runs a network and infrastructure and one of his personal goals is to improve his public speaking. I am giving him an opportunity to present to the IT organization how they accomplished getting us remote in less than three weeks. This is an opportunity to give huge recognition to the team and celebrate them, but I want him to step out of his comfort zone and reach across to different parts of the IT organization.

Beth O’Rorke, Chief Information Officer at Commonwealth Health Alliance

It is important to think like a business person and learn about the business, what makes the business run and how one can look at technology as a way to enable opportunities for growth or solve a pain point. I would say one should let your career path naturally happen, although raise your hand for tough assignments.  Those who over-manage their career really don’t get too far.

In fact, you shouldn’t be shy about raising your hand for something that’s a little bit out of your comfort zone — not the traditional IT thing — and let it elevate you to that next point of learning. In technology, if you’re not learning you’re dead. Technology is moving so fast that you must stay up with it. If you ever think you’re done learning (which includes life), that is a big mistake.

Shahid Alam, Chief Digital Officer at Circulo Health

Let me start with an example. If you ask someone, “Is Amazon a technology company, a retail company or an online company?” there will be a whole lot of debate around that. The reason is that they do all of that well. They have figured out how to sell goods using technology and at the same time be consumer-focused. One could argue that they are really a consumer engagement company because they do that so well. One could argue that they’re actually a technology organization. What I would say is that their technology organization really understands what it is that their business is trying to solve. They figured out how to combine those two together in a way that they don’t think about it as two different elements – technology versus business.

The point is that, for up-and-coming CIOs, my suggestion would be first and foremost to understand the business. What is the overall business objective? What is it that you want to be your competitive advantage in your business and then focus on that and figure out the technology that’s going to solve that.

Don’t be afraid. Don’t get pigeonholed early in your career even though it is easier. Open your horizon. Broaden your skillset. That will help you to build an appreciation for every part of the organization. Sharing my experience, I worked as a software engineer; I worked as a database developer; I worked as a business analyst; I worked as a project coordinator; I worked as a project manager; I worked as a data analyst. Looking back, it’s probably the best thing I could have done to gain an understanding across the spectrum of all this activity that’s happening across the organization. My advice to the aspiring CIO would be don’t be afraid to do things that are not in your wheelhouse. Broaden your horizon, especially in things that you’re uncomfortable with. More importantly, don’t be afraid to ask questions and learn the business. I tell my team every day: If you’re working on a project and you don’t know how your work is going to solve the business problem, you should stop, go talk to your business partners and ask, “What is it that you’re trying to do?” And then, how does that align with their overall strategic objective?

Grant Shih, Chief Information Officer at National DCP, LLC

So many people look for the answer in this path as a checklist. I would challenge them to reframe that thinking. First, don’t define it as things that are necessarily measurable. It’s not about getting certificates, it’s not about going to a data brief. Those are all good experiences, but at the end of the day, it’s not about the technical search. It’s not about how well you can code in something or how well you know the architecture and can design cloud strategies. It’s about understanding the relative importance of those things, when to apply them, and the ramifications. You must also identify and understand your endgame. Are you trying to just be a CIO or CTO? Once you get there, are you like a dog chasing a bumper? What do you do when you catch it?

Adrian Butler, Chief Information Officer at Casey’s General Stores

Be inquisitive. Be open to new things, new ideas, new ways, new approaches. In my journey, I’ve been unafraid to take opportunities that didn’t necessarily fit with how others may have perceived the world order to be. I’ve lived in several different places, so demonstrating courage by being open to moving has been a big part of that for me.

Another is, when you don’t know something, seek out those who you admire. Develop peer mentoring relationships. The biggest part of my journey has been what people have poured into me. What I’ve learned in my career is what I give is always reciprocated at multiple folds. Invest in others and create a network that you can rely on as your career evolves. You’ll learn technologies as you go, but the relationships that you establish and how you go about this journey is what will be your testament in the end.

Deepak Kaul, Chief Information Officer at Zebra Technologies (Former)

I would tell them that this role is not just limited to technology. It’s about your ability to stand up a smart and diverse team. It is about creating a great work culture that provides professional development, personal fulfillment and generates results.

The aspiring CIO should also expect to champion innovation and continually strive to optimize processes and technology. This role touches everybody in a company in some fashion. You need to be business savvy and facilitate cross-functional alignment.

As a general manager of your function, you will have to be accountable for balancing the value delivered against the costs incurred.

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