Employees increasingly expect enterprise software to be as intuitive as the consumer apps they use every day. For CIOs, meeting those expectations means modernizing workflows while deploying AI without compromising security or accuracy. That balancing act is particularly important in the legal industry, where mistakes can have significant reputational and regulatory consequences.

“As CIOs we need to understand where to quickly leverage the opportunities that AI creates, while managing risks and adhering to our client requirements,” said Crowell & Moring CIO Andrea Markstrom, who joined the firm in June 2026. “That's the pressure that we're under right now: To go fast, but go safely.”

The legal industry has been quick to embrace AI. Overall, 80% of legal professionals expect the technology to impact their work, according to a Thomson Reuters survey. But while the opportunity for AI is immense, law firms have to tread lightly. Accuracy and security concerns remain the biggest barriers to adoption. Mistakes can become front-page news. And given the sensitive nature of the data they protect, law firms can’t risk a breach.

Navigating these challenges, Crowell & Moring has pursued AI on multiple fronts. The firm's Innovation department launched an internal AI assistant for the firm designed to securely access proprietary data. It partnered with legal AI provider Legora to help practices areas streamline research and processes. And it’s using Microsoft Copilot across finance, HR, and marketing departments. Crowell’s CIO and Chief Innovation Officer, Alma Asay partner closely on advancing AI for the firm.

To accelerate these efforts, Andrea keeps the focus on people — aligning talent with business priorities while encouraging her team to learn from both internal stakeholders and external networks.

“It’s easy to say: ‘This is how we’ve always done things,’” she said. “I’m here to challenge that, to impress upon new ways of working ,and enhance our communication and client service with emerging technology.”

As AI forces CIOs to rethink how they lead, CIOnews talked to Andrea about the core principles for any user-focused technology strategy.

Start with the user

Before pivoting to the legal industry, Andrea spent years in IT leadership at Target. Working in the retail sector taught Andrea the importance of the user experience, as well as the need to run IT like a business. But the shift to the legal sector meant adjusting to a new reality with many more stakeholders. To minimize the learning curve, Andrea sat in on client meetings, depositions and trials to learn what it’s really like to work inside a law firm.

“I started to understand how we can better serve our internal customers from an IT standpoint. I would not have been able to do that if I didn't take the time to learn from our stakeholders,” she said.

That emphasis on real-world experience has stayed with her. CIOs can’t adequately serve stakeholders without understanding the actual pain points they face every day, Andrea argued. And teams have to shift from a buying mindset to one based on outcomes.

“I almost hate to say IT organization anymore. We’re a business partner,” she said. “It’s not about technology solutions anymore. It’s making sure we are meeting the demands of our internal and external clients, and that goes far beyond technology enablement.”

Build the right team

Understanding users is only part of the equation. And delivering AI transformation means reshaping both the IT landscape and organization itself. Talent gaps can drag on AI adoption efforts as much as technical deficits. Key skills remain in short supply. And roles are often misaligned with evolving company-wide priorities.

The solution goes beyond hiring. When it comes to matching people to responsibilities, Andrea looks to Good to Great by Jim Collins. For nearly three decades, Collins' management philosophy has influenced business leaders like former Amazon CEO Jeff Bezos and former Netflix CEO Reed Hastings. Among other teachings, Collins urges businesses to prioritize talent and make sure employee skillsets are matched to the right roles.

To put this into practice, Andrea asks her teams to identify outdated responsibilities, skill gaps, and opportunities to redirect resources toward higher-priority work. Ultimately, this exercise gives employees the opportunity to contribute at a higher level.

“You start to see people’s eyes light up because they've been waiting for this opportunity to expand their career and take on new challenges,” said Andrea. “This intense focus on people makes the difference, not only emphasizing the value they can deliver to the organization, but that we drive success as one, unified team.”

Learn from the network

Andrea’s career pivots, including from Target to the legal industry, were a result of connections she nurtured: “I’m deeply grateful for my network, because it truly takes a village.  Being rich in authentic relationships is incredibly important – success is rooted in gratitude and building genuine, dynamic connections along the way," she said.

For Andrea, a strong network is also foundational to developing a winning technology strategy. Knowing what peers are investing in, their successes, and lessons learned helps inform Crowell & Moring’s own IT transformation.

Networks should also expand beyond professional circles, Andrea said. The role IT leaders play in their communities is just as important. Andrea is founder and CEO of Inspiring Women Igniting Leadership and Learning, i.WILL. The organization focuses on mentoring and professional development, and runs events like “Shark Tank”-style pitch competitions.

“We can do more, not only within our internal organizations, to inspire and empower others,” Andrea said.

As AI reshapes how employees work and the technology they need to be successful, it’s the CIOs who understand their users, invest in talent, and cultivate strong networks that will be better positioned to lead that change.