8 tips for cultivating a winning IT culture

Great IT organizations don’t happen by accident. Building a winning team requires dedication, support, and imagination.

Winning IT organizations aren’t built in a day. Long-term success is generally the result of leaders who make a committed effort to connect directly with their teams, rather than simply issuing memos, edicts, and other top-down commands.

Employees want to work for leaders who inspire them, engage them, challenge them, and give them opportunities to grow and be effective, says Ola Chowning, a partner with technology research and advisory firm ISG. “Engagement and trust hinge on clear values and transparency,” she adds. “Employees who aren’t just informed of objectives, but given a sense of responsibility, are more comfortable with their roles and tend to enjoy the challenge of being a key driver of excellent performance.”

Are you looking to build a winning IT culture? The following management practices will help you get there.

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1. Foster adaptability and flexibility

Adaptable work environments and agile methodologies form the bedrock of a thriving IT culture, says Charman Hayes, executive vice president of people and capability for the technology group at Mastercard.

Flexibility is vital to Mastercard and its IT team members, Hayes says, “from the location of our offices to the role of our tech hubs to new tools and technologies that help us work seamlessly and effectively.” Hayes notes that the company’s ongoing focus on collaboration and flexibility includes the availability of hybrid work, ‘work-from-elsewhere’ weeks, ‘meeting-free’ days, and end-of-week flex time.

“We recognize that technology teams need deep concentration time to create new solutions as well as efficient ways to work collaboratively, and our flexible policies are designed to enable that,” she says.

2. Invest in and encourage talent development

Encouraging ongoing learning and curiosity is a top priority at Liberty Mutual Group, says EVP and CIO Monica Caldas. “People are often surprised to hear that Liberty Mutual invented the emergency stop button on escalators,” she states. “We have an innovation spirit that’s ingrained into who we are as a company.” Caldas says that innovation today includes the adoption of promising new technologies, such as generative AI and open frameworks. “Projects that really excite our teams.”

Caldas has no doubt that technology is a key differentiator. “We have aligned our technology strategy to be a business strategy,” she says. “We want transparency about the roles available across the organization and give employees the right tools to identify growth and job opportunities as well as skills development.” Caldas adds that team members are encouraged to develop themselves through various career paths, leading to long, meaningful futures.

A winning IT culture comes in two parts: innovation and connection, says Brad Smith, CIO at payroll software provider Paycom. “Our IT team has an opportunity to be on the forefront of tech innovation. When every employee is unified under this collective goal, they establish a strong connection and work toward winning together.”

When IT connects the dots between innovation and building a technology to simplify lives, it creates a motivated workforce determined to enhance productivity, Smith says. “When this drive partners with a focus on business outcomes and direct impact, you have a team of innovative IT professionals working together to do something amazing.”

4. Embrace new challenges and prioritize engaging pilots

Justin Rodenbostel, executive vice president at technology modernization firm SPR, believes that emphasizing learning, training, and professional growth is crucial. “Team members who can find and respond to new challenges are more engaged and, over time, become well-rounded professionals who are more valuable to their organizations,” he explains.

Rodenbostel suggests starting small. “Secure funding, design a program for a small group of individuals, and run a pilot,” he advises. “Before starting the pilot, identify how you will judge success, perhaps by using a combination of qualitative and quantitative measures.” From a quantitative view, Rodenbostel advises considering measures such as a reduction in turnover or an increase in internal or external customer satisfaction. For a qualitative view, employee surveys that measure engagement or information from front-line managers can be used. “Use that pilot group to determine what works best inside your organization and with your team members.”

5. Be authentic

A winning IT culture requires an authentic IT leader, says Jay Upchurch, executive vice president and CIO at business software firm SAS. “For some people, authenticity can be uncomfortable because it requires transparency and vulnerability,” he warns. Yet authenticity draws employees in and builds trust. “Trust is quickly followed by freedom of thought, innovation, diversity, and courage,” Upchurch notes. He adds that authenticity doesn’t require always being right. “Being authentic means you embrace being wrong in a transparent manner,” he explains.

Upchurch advises communicating clearly and frequently about your overall IT vision. “Be realistic about what’s achievable and build an organizational structure and processes that will help the team work toward that vision.” He also recommends listening to your team and being open to change. “When an IT leader does this, two things happen: Great ideas will emerge, and it allows the leader to admit when he or she is wrong.”

6. Focus on transparency and alignment

An effective leader clearly communicates organizational goals that align with the overall enterprise mission, says Sandeep Angra, CTO at commercial aviation services provider Unifi Aviation.

Effective communication, a compelling vision, and fostering collaboration across departments are all crucial, Angra explains. “Recognizing and rewarding achievements, promoting continuous learning, and using feedback for improvement creates an environment that allows teamwork, innovation, and alignment with the organization’s broader objectives.”

Angra suggests building a dynamic IT roadmap that is closely tied to business strategy and is continuously refined by input from relevant stakeholders. “IT leaders should actively engage in this process, ensuring a deep understanding of their roles, business needs, and areas of concern.”

Building a winning IT culture is an ongoing journey, Angra observes. “Start by defining clear guiding principles and apply those principles to your daily actions and decisions,” he advises. “Ensure that every leader in the organization hears and sees these principles being applied consistently.”

Over time, established IT principles will become a natural part of the organizational culture, guiding behavior and decisions. “Remember that building a winning IT culture is an ongoing process, and the consistency of your actions and leadership will play a key role in building a winning IT culture,” Angra says.

7. Establish uniform guidelines

An accomplished CIO establishes precisely defined rules, setting practices and procedures that apply throughout the organization, regardless of position or rank.

Organization guidelines should be both comprehensive and fair. “One strategy is to constantly provide and invite feedback when people feel incorrect choices are being made,” says Jeremy Freeman, CTO at business intelligence software provider Allstacks. He recommends following a coaching and feedback model. “When you detect a problem, bring it up immediately,” Freeman advises. “This approach allows you to focus on the impacts of bad culture in day-to-day interactions.”

Freeman warns against slipping into a command-and-control based organization. While there are times when it may be needed, taking a rigid management stance may create a false sense of alignment. “What you see as a ‘winning’ culture, may just be fear-based compliance,” he says. “When you give people the autonomy and coaching to make their own positive decisions, they start to understand why these things are important, and it’s never just because the ‘boss said so.’”

8. Support team challenges and growth

Lydia Lightfoot, lead IT recruiter at staffing and recruiting firm Carex Consulting Group, says one of the things she hears most from IT job candidates is a desire for challenge and growth. “Providing opportunities for growth is a great foundation for building a winning tech culture, whether it’s promotion, upskilling, attending conferences, new project work, or all of the above.”

Passions common among tech pros include problem-solving, a desire to learn new technologies, and seeing the outcome of their work. “Supporting your team and making sure they’re achieving these things is incredibly important,” Lightfoot says. “People want to feel heard and supported.”

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