How to level up from IT management to IT leadership

Oliver Galicki no longer needs to envision what it would be like to ascend to the CIO role. He’s just landed one.

On Aug. 10, Galicki transitioned from VP of clinical applications and engineering at Memorial Hermann Health System to become deputy CIO and VP of applications at Medstar Health System. He attributes his new job to having cultivated a combination of technical and soft skills over the course of his career.

“The foundation of understanding technology and having done some hands-on work earlier in my career has helped me be able to ask the right questions and help drive the right business value and outcomes for our clinical operators,” Galicki says. “But in the second half of my career, it’s been more around the soft skills; the relationship building, the creation of trust. How do you solve problems for the organization that takes it to the next level.”

That combination is essential for IT leaders today, says Peter Birch, director of technology and digital executive search at Harvey Nash.

Stand-out candidates for C-suite tech exec roles must have “a deep and broad track record of driving change and transformation underpinned by innovative tech-based solutions,” Birch says. “These leaders are also required to be highly commercial operators, able to master corporate engagement, and speak the language of the board.”

Moreover, climbing the IT leadership ladder requires demonstrating “the value return they can bring to the CIO role for the wider business enterprise,” he adds.

That means taking on big initiatives, learning from mistakes, developing business acumen, and finding strong mentors along the way.

Here, Galicki and recipients of CIO.com’s inaugural Next CIO Awards discuss what it takes to level up from mid-level IT management to senior IT leadership positions today.

Leading with business acumen

Trista Huang says that what has helped her stand out from the “majority of technologists” is her business acumen and her drive learn more.

“I always have taken extra certificate courses in the field that I worked on,” she says.

After receiving an undergraduate marketing degree and then an MBA, Huang’s career trajectory was more business-focused, with stints as a business analyst, portfolio manager, and project manager.

Along the way, however, Huang “learned my way into the technical side” by taking programming classes at New York University and getting certifications in project management, as well as agile and waterfall methodologies.

Now vice president of technology and analytics at Blackstone Real Estate Hotels and Resorts, Huang aspires to become a CIO change-maker.

“I want to show the business and help the business to generate competitive advantage to create something that business couldn’t do before, leveraging technology and leveraging data,” she says.

Huang attributes her rise in leadership in part to her ability to communicate.

“You don’t dive down to nitty-gritty details — or you dive into the very nitty-gritty details — but tailor your answer to the audience and you never, never sound condescending,” she says.

Tone is important, Huang adds, as is using laymen’s terms and giving straightforward answers, “not running people in circles. That is also important as you rise to a leadership level.”

So is gaining a deep understanding of the business. Here is where Huang’s experience on the business side has paid off, as most technologists who rely heavily on their business counterparts for guidance have to wait for those business colleagues to tell them what to do.

“You can’t think outside the box if you don’t know the business,” she says, advising aspiring leaders to emphasize team building and empathy as well. “That takes soft skills — how you talk to people, get buy in.”

The strategic impact of technical experience

Jerry Imsand has taken a more technical route to IT leadership.

With more than three decades in IT, Imsand’s experience spans infrastructure, cybersecurity, identity and access management, enterprise architecture, master data management, business intelligence, digital services, and now AI.

That broad technical resume gives him a unique perspective on how interconnected IT systems can advance the organizational mission.

“Throughout my career, I have intentionally sought opportunities to understand not just the technology itself, but how technology enables business and government to better serve people,” says Imsand, deputy CTO for the Tennessee Department of Finance and Administration Strategic Technology Solutions.

“My career has evolved from being deeply technical to leading organizations where strategy, innovation, and developing people are every bit as important as the technology itself,” he adds.

Imsand aspires to be a CTO or CIO due to the opportunity those roles have to shape organizational strategy, build high-performing teams, and ensure technology investments create measurable value for citizens, customers, and the organization.

Having a just-do-it attitude

Kari Johnson, deputy CIO and chief data and analytics officer for the City of Scottsdale, Ariz., has worked in IT for about 20 years — since before it was called IT, she says.

Her early career focused on data and systems, and eventually, Johnson went back to school to get a bachelor’s degree in computer science.

Consulting work enabled her to become involved in all aspects of the business — from setting up email systems to ordering and installing fiber.

“I would see things and say, ‘We could improve this, add more people, make something more enterprise,’” Johnson recalls, adding that this problem-solving capacity and curiosity have been vital to her career.

“I’m a just-do-it kind of person. If I see something that can be improved or improves the life of someone else … I make it a point to learn about it and see what I can do to help improve it,” she says.

Johnson wants to keep moving up the leadership ladder, but she doesn’t necessarily tie fulfillment and value to titles. “I just keep aspiring to be that leader that brings other people along, because someone brought me along,” she says.

Taking big swings — and learning from mistakes

For most ascending IT professionals, the stretch assignment marks a rite of passage. Moving up from mid-level IT management to IT leadership is often accompanied by a big (potentially make or break) project to lead and learn from. Galicki, this involved being tasked with taking on the $400 million-plus implementation of Memorial Hermann’s Epic electronic health records system. It was a two-year project with a team of roughly 350 to 400 IT people.

In hindsight, there were things he would have done differently, Galicki says.

“We could have a done a more timely job [of] deployment,” he notes.

IT added 9,000 mobile devices and rolled out the Epic system the same day. That created “a very confused end-user nurse experience.”

“I’ve looked back on that and thought, ‘Man, that should not have been our biggest distraction on day one of our big go live,’” he says.

Galicki also gained greater perspective as a result of the experience.

“What I’ve learned is you have to take a step back. You have to remember that a health system is never doing just one thing — even if it’s the biggest objective,” he says. “Step back and put yourself in the perspective of end-users that you’re bringing change to.” Echoing Huang, Galicki says empathy is essential because every tech project brings a layer of change.

For Imsand, focusing on building the right technical solution has also taught him the importance of ensuring everyone understands why the intended change matters.

“I learned that even the best technology can struggle if stakeholders are not engaged early and often,” he says. “Today, I spend considerably more time communicating the vision, listening to concerns, building alignment, and creating ownership before implementation begins.”

Imsand has also learned that not every opportunity needs to be pursued immediately.

“Prioritization is just as important as innovation,” he stresses. “Some of the best leadership decisions involve knowing what not to do so the organization can focus its time, resources, and energy on what creates the greatest value.”

As for her learning experiences, Huang points to failed projects that didn’t make it to production.

Most mistakes were made by “overly trusting the information people gave on timelines,” she says, as well as not fully understanding why certain milestones hit delays and giving stakeholders too much confidence that a team would be able to conquer a roadblock.

“I could have dived deeper,” she admits, noting that not taking the extra step caused delays that had domino effects.

Finding great mentors

Often, IT managers don’t get to where they are on their own. Galicki attributes his rise in leadership to having great mentors along the way.

“You don’t grow in leadership in general, but certainly in the IT world within a health system, without learning why decisions were made, how to lead, how to work within the organization, and I think IT leadership is no different,” he says. “You’ve got to go out and build trust from that.”

Learning from mentors is critical, but so is building alignment with the end-users, Galicki adds.

Huang agrees, saying her mentor is her CTO and boss Amol Kale.

“He’s a very big part of my growing journey,” she says. “He has given me lot of tips on how to manage down and being a good manager.” Learning how to manage down is equally important to managing up, Huang notes.

Kale has also made Huang aware of her tone of voice. Noting that she is a New Yorker who talks fast, Huang says Kale often tells her to slow down. Sometimes, Huang says, she doesn’t recognize that “my tone can come across as a little harsh, a little too fast.”

Feedback like that can be vital — and sometimes hard to come by. Huang and others advise aspiring IT leaders to seek that out by first building trust.

“Definitely someone that you trust and you constantly get feedback from is very important,” she says.

How to rise from IT manager to IT leadership

Candidates for IT leadership roles generally spend between five and 10 years operating in a director-level capacity, perhaps reporting to a CIO, Harvey Nash’s Birch notes.

“If the candidate has the drive, broad technology understanding, commercial expertise, and the ability to inspire and lead diverse groups of professionals, then they may well be approached for their first C-suite position,” he says. “Perhaps they would move from being a direct report of a global CIO in a large corporate, complex business to being a CIO themselves.”

While many organizations focus on succession management to ensure that when their CXO departs there is someone ready to step into the role for a seamless transition, internal promotion is not always appropriate, Birch notes. “Often, with a change at the board level or across the C-suite, there is an appetite to bring in alternative technology leadership who can deliver new ideas and ways of doing things.”

Regardless, there are measures IT managers can take to make themselves more visible and valuable. Huang and Imsand both advise building relationships across the organization, not just within IT.

“Spend time forming human connections. That goes a long way. Technology, you can always learn online — we forget the human connection,” Huang says. “Show genuine interest in other people; that’s the best way to form connections. People like to talk about themselves. That’s how you learn.”

Galicki is a firm believer in getting outside of IT to learn more about the changes and problems businesspeople are trying to solve.

“If you sit behind a desk,” he says, “you’re losing out on at least half the picture of what we do day to day.” He also advises asking questions. “The more you ask about the business of healthcare, the more you can support” business units. “Don’t be an order taker.”

Also, Imsand advises against defining yourself by your current job title. Like Johnson, he says you should become known as someone who consistently solves organizational problems.

“Develop expertise beyond technology,” Imsand adds. “Learn how budgets are built, understand procurement, governance, risk management, and business strategy.”

Johnson recommends doing the job you aspire to — with executive buy-in. She also stresses not to dwell on mistakes. “We all mess up every day up to highest level, and if you don’t put yourself out there, you’re not going to go anywhere,” she says.

Imsand also believes it’s worth investing in your communication skills. “Senior leaders spend far more time explaining, influencing, mentoring, and aligning people than configuring technology.”

And IT managers should invest in developing others, he says.

“As your career progresses, your success becomes less about what you accomplish personally and more about what your team accomplishes because of your leadership,” Imsand explains.

What leadership is really about

Johnson has a more philosophical perspective on what it takes to become a leader.

“Leadership isn’t your title or job assignments, it’s what you do to bring other people on board and move mountains to get things done,” she says. “The best leaders I’ve known … it’s literally the essence of who they are.”

Even as she doesn’t emphasize job titles, Johnson admits that when the right opportunity comes along, she wants to become a CIO. But she believes there is more room in the C-suite for other tech executives — and she wouldn’t mind a title with AI in it.

“I think we’re going to end up realizing at the CIO level there is another job of that same C-suite level that is enterprise data and CIO,” since the CIO can’t do everything, Johnson says. “There’s all the data and infrastructure to take care of and more of the business.” That might leave room for an equitable C-level position that’s concentrated on data and AI, she says.

“Maybe we stop calling things ‘data’ and ‘AI’ and we start calling that enterprise information,” Johnson muses. “Maybe I will invent another title for myself.”

See also:

• 8 IT leadership tips for first-time CIOs
• 5 tips for future-proofing your IT leadership career
• 6 new rules of IT leadership — and what they replace