by Esther Shein

Top career tips for aspiring CIOs

Nov 18, 201913 mins
CareersCIOIT Leadership

CIOs share hard-earned lessons and time-honored advice to those seeking top technology leadership roles.

executives on the move stairs career promotion upward steps
Credit: metamorworks / Getty Images

Romain Apert likes to tell a story he heard from a mathematician who talked about the analogy of a dark room, and how a person attempts to find the light switch but bumps into an object when they move to the left or the right — but as they continue moving forward, they gain more information to make sense of the room.

“Finally, one day, you find your way to the light switch,” says Apert, vice president and global CIO of Mars Wrigley. Whereas once, CIOs were “just a bunch of leaders who used to be very successful in a room that was focused on standardization, simplification and globalization, where it was very much back office,” now, “these leaders have been thrown overnight into a dark room.” The challenge, as Apert sees it, is for them to find their way to the switch.

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“The only way to find your way is to learn; learn why the room is dark and identify the best way to find your way to the switch,’’ he says.

That’s a lesson that is applicable not only for CIOs, but tech professionals who aspire to move into the C-suite. Like technology itself, the CIO role has evolved and continues to evolve. Here are some tips and advice from IT leaders on how to become a CIO and what they’ve learned along the way.

Strategy first, solutions second

When Steve Dee became CIO at J.Crew Group in 2006, the role was all about execution. “I was told, ‘Just deliver solutions,’” he recalls, “so I felt like leadership was telling me, ‘You should been seen and not heard.’ I really had to fight for a seat at the table.”

Now, because of the impact technology has on a business and how tied it is to driving value, business leaders look to him for his opinions, says Dee, who recently became the first CIO at Rodan+Fields, a multilevel marketing company specializing in skincare. “I’m part of solving the problem, not just providing a system.”

Dee no longer feels he has to fight for a seat at the table. In fact, he says he is also being asked more frequently to take on leadership of traditional business teams and look more outward toward consumers, as well as to internal users.

“Technology is at the heart of every business that’s great and if it’s not then you’re probably not a good company,’’ says Joy Driscoll Durling, CIO of Vivint Smart Home. “The role has evolved by taking technology and turning into a strategic asset for a company and it permeates every aspect of company.”

Ultimately, technology powers every interaction a company has with its customers and employees, she says, and customer and employee expectations have never been so high. 

The CIO role is no longer only about operating systems or boxes with blinking lights, says Scott Laverty, executive vice president and CIO at Shane Co. “It has evolved to being a participant [who] is setting the overall strategy of a company and aligning technology to enable the same.”

Driscoll Durling calls the CIO position “the hardest job in the C-suite,” because the role is unique in the sense that it sits within every other business unit and function. “It’s the white space that connects all business units and functions and it requires a leader to juggle three big balls,’’ she says. They are: Always create technology that drives revenue and growth for the company; drive solutions to save money so the company can become more profitable; and manage risk and prepare the company for scale. 

Understand the business

Laverty was working as a consultant for Deloitte, which had bid on an Oracle retail implementation at the now-defunct Borders Books and lost the bid. Laverty gave Borders a list of things to look at when the implementation was finished.

“They called me a week before Thanksgiving and they had lost track of millions of dollars’ worth of inventory,’’ Laverty recalls, because interfaces weren’t correctly installed. He went in and fixed the problem. A few years later, the new CEO of Borders asked who had fixed the system, “and hunted me down and hired me” as CIO.

“I had never thought about being a CIO, but I realized I could do the job,’’ says Laverty, who spent about two years at Borders as CIO.

Driscoll During agrees, saying she didn’t have a formal computer science education. “I learned how to do my job by understanding my business, my customers and how technology can be a critical enabler,’’ she says. “I got in the trenches on the tech side early in my career with large CRM implementations, as well as marketing and sales system overhauls.”

The key to success is always the same, says Driscoll Durling: Understand what business and customer problem you need to solve.

Given how technology plays a strong role in many aspects of people’s business and personal lives, the lines between the “business” and “technology” are blurring, says Dee. A CIO should make conducting business easier, and he believes it is possible to become a CIO from the business side. 

“One caveat is that you have to be willing to put in the time to understand the patterns and culture of a technology department, much like a technologist has to understand the business,’’ he says. 

Stretch your skills

Be open to new opportunities and be willing to take risks, says Dee. “I always try to look for opportunities outside of my job description to help me add additional value,’’ he says. Those opportunities also give Dee the chance to work on areas of weakness or learn a new skill. “The more varied your technology experiences are, the better CIO you will be.” 

He also advises aspiring CIOs to surround themselves with others who are “superior in their area of expertise,” as this will help the former learn how to be better themselves. “Take time to understand the business and culture in which you are working.”

Laverty stresses that you shouldn’t just focus on technology. “Learn your business and learn your customers.” And, he adds, “You can never communicate enough. Period.”

And Apert recommends focusing on the importance of learning, “and I should say, the importance of unlearning.” Unlearning agility, he explains, “is becoming the most important driver for successful careers.”

This means aspiring CIOs should challenge their intuitions and beliefs “built in a world that was very predictable, in a room where you could see everything, he says. “Challenge yourself to learn new things that are meaningful and purposeful whenever you enter a dark room. Sometimes they’re the same thing, sometimes they’re a completely new approach.” Also, learn to deliver meaningful solutions and not technology for the sake of technology, he says.

Demonstrate early on how you will fill in your blind spots, says Driscoll Durling. “With advances in everything from AI and machine learning to cloud and open source technologies, it’s impossible to be a subject matter expert in all of it.”

She educates herself by reading a lot, connecting consistently with fellow tech and CIO colleagues, and hiring aggressively. “I use a lot of my commute time to share ideas and get advice from people I respect,’’ Driscoll Durling says.

The value of adaptability — and admitting you’re wrong

Just because you’re a CIO, it doesn’t mean your technology decisions are always right, says Curt Gooden, CIO of TaskUs. “Recognize what you don’t know and be willing to know you’re not always right and that there are experts out there you can rely on,’’ he says.

And be adaptable to change, as IT no longer has the luxury of deploying projects over a long period, he adds. System development is now a constantly iterative process and teams have to continually monitor whether something needs to be adjusted or changed. “It’s constant evaluation and re-evaluation,’’ says Gooden.

For example, Gooden has gone into projects with a set idea about what technology to use with a particular design in mind. “We started going down a path of spec’ing it out and getting a team to design it along with a vendor, and at the end of the day my team did some analysis and said, ‘This isn’t the right approach,’” Gooden says. “They made a good case and it made absolute sense.”

He says he will “always admit if I’m not right. I admire a team that puts numbers together and recognizes that we’re not going down the right path.”

Humility and diversity can spark innovation

Apert echoes that, saying you need to show humility and be willing to learn from anyone in the organization, since “you might just be wrong, and here’s a different way to look at this problem.” As Mars Wrigley recruits new talent, especially those with skills in blockchain and AI, “most of the ideas are coming from the bottom of the organization.”

He also recommends that IT leaders encourage new ideas. They should be willing to learn from others and shift their mindset so someone can bring an idea forward, “and I put my judgment on hold to give this idea a chance and see if value can be created from it,’’ he says.

For Dee, it’s the importance of building diverse teams and not just hiring people “that look and sound like you, that aren’t willing to challenge you,’’ he says. When it comes to infrastructure, networking, consumer interfaces, UX and UI design, “you can’t necessarily be the smartest people in the room on all those things. So I’d rather hire those people to educate me and pull our business forward.”

Key skills for future CIOs

Whereas in the past, CIOs needed to know about how to implement software packages and build data centers, today’s CIOs need to know about cloud computing, data privacy regulations and how to deliver customer experiences, says Dee. Advances in machine learning and AI are also good skills to have. “But at the end of the day, it’s all about figuring out how to deliver quality at speed.”

“The tech side is great, but you’ve got to spend time understanding your consumer as well as your internal users and you really have to understand that the barrier to entry is low because of cloud computing,’’ he says.

It’s also important to know how to ramp up a system quickly. “Luckily, young and new CIOs have spent time exploring that world — but that didn’t exist when I started,’’ Dee says.

Apert says aspiring CIOs need to know how to follow adaptive problem-solving methodologies such as agile and building prototypes and show them to users as quickly as possible to assess whether they are meeting customer needs. “As we learn about the success or the failure of those prototypes we need to adjust our beliefs about the world,’’ he says.

Passing along time-honored advice

Prior to becoming a CIO, Laverty says he was able to keep all the balls in the air. “Once I became a CIO, I had to learn to decide which ones would drop, because when you become a CIO you have more thrown at you than ever.” As a consultant Laverty could control his scope — but as a CIO, he learned quickly that “you’re on receiving end of a fire hose.”

Dee was told that when communicating, “make sure your message hits their mind not just their ears. Just because you said it doesn’t mean they understand it.” At Rodan+Fields his business stakeholders and consumers often focus on the “bright shiny reward, so you have to make sure the ramifications of action and inaction are clearly understood.”

The one thing that has always resonated with Driscoll Durling — and which she says she has yet to master — is setting the right pace. “CIO is one of the hardest jobs in the C-suite. There’s always more things to build, always more things to fix, always more things that are broken. Technology is the most perfect imperfect business because things always break” so CIOs and their teams could become exhausted unless they set the right pace and figure out a natural rhythm, she says.

She was also advised to find advocates in the C-suite and foster deep relationships. “That tends to be women who have to lean in harder,’’ she says.

The best advice Gooden received that has stayed with him has been to “make sure you’re always looking at everything you do thru the lens of the business.”

Apert has learned that whenever he changes roles, it’s important to spend quality time immersing himself in the business, “and I try not to make any judgments during that phase,’’ he adds. “It’s all about learning from different angles, and the more you grow in an organization, the more complexity you face.” This requires greater diversity of input to assess a situation, he says.  

Other advice he’s received over time is to be very good at something, whether it’s deep technical expertise or being a great storyteller. “You have to differentiate yourself, so spend time learning and make yourself a unique talent in your industry.”

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