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Derek Cullen has been advocating for new technology for years. As Chief Information Officer at Stikeman Elliott, he leads cloud migration, cybersecurity programs implementation and digital transformation initiatives. However, AI is different.
“This is the first technology project in nine years here. I go to the board like I did in the cloud and say that this is why I want to go to the cloud, and the board comes to me and says, ‘How do you get this done?’ “We want to be there. This is a transformation. We want to sell quickly by using Genai in our professional services, but not the last. We want to prepare for this because it’s coming.”
This shift from CIO’s push technology to pulling CEO, chair or board shows a turning point. AI is more than just another tool. It’s changing how leaders think about the role of technology in business.
Karen explores this transformation at the CIO Association’s Canadian Association Peer Forum, where he moderates the Ai-Augmented panel on leadership. The discussion focuses on how CIOs integrate Genai into decision-making and business strategy, navigating both their possibilities and risks.
In Cullen’s case, AI is more than just a software upgrade. This is a fundamental change in the way technology leaders operate.
He argues it’s important to make sure AI is a critical part of your toolkit. At the same time, leaders need to address every aspect of AI implementation across the organization, whether it be risk, business transformation, or other important areas.
Karen sees AI rebuilding workflows in two important ways.
Increased productivity: Automating repetitive back-office tasks in areas such as financial operations, business development, and marketing. Transforming service delivery: Change the way law firms, banks, and businesses conduct research and potentially produce work products.
However, AI can increase efficiency, but Karen warns that he is in a hurry without a clear plan. He says that because there are so many players in the AI field, many of the technology has not yet been standardized or fully tested.
“Some of that is still encapsulated in a lot of hype,” he says. Without proper review, organizations risk being disappointed by their growing expectations. “If executives are asking them to reach the finish line, they need to be very clear that there is an assumption that some of this is hype and fiction until they actually test it out and prove their use case.”
He also points out that the complexity of AI integration is underestimated as a barrier to many. Executives may expect immediate results, but reality is much more complicated.
“The executives would like to use the genai solution to look into all of the past 50 transactions we’ve worked on, do all the transactions we’ve worked on real estate transactions, and draft RFP responses for new transactions. In many environments, genai (needs access) has potentially more than 12 data sources. That’s a big effort.”
Many executives now say these types of genai solutions are data in place, available and accurate, and say the integration itself requires careful thought and work.
Balance between innovation and risk
As a technology leader at a law firm, Karen approaches AI with additional caution, especially when it comes to client data. AI can increase productivity in back-office operations, but it requires a more measured approach for use in legal work.
“The law firm and our clients are so risk-averse, that’s a delicate tightrope walk we’re walking right now,” he explains. “Because this is an exploratory approach, we understand the technology, try them out, pilot them, and plan the applicable use cases.”
Karen says he is moving forward with careful optimism waiting for his company to fully understand the risks and rewards of AI.
The tension between AI efficiency and the need for legal industry accuracy reflects the broader challenges faced by CIOs. As AI is embedded in more enterprise tools, leaders need to balance automation and accountability.
“You may think they’re not training on your model. You may think they’re not using your data. Sometimes they do,” warns Karen. “Be very careful about what you’re doing with your data. IP is very important.”
Even with internal legal expertise, AI contractual risks can be challenging.
“We are a law firm, but it takes time to check the terms of AI vendors,” he says. “You might think you understand that you signed up, but sometimes fine print tells you something else. I had to be very careful about making sure your data stayed protected.”
What to expect from Karen’s panel on the Peer Forum
As technology leaders are not yet sure about the role of AI in leadership, the CIO Peer Forum Cullen panel provides concrete insights from technology executives who have already integrated AI into their strategy.
“What I hope people will take away from now is hearing the success stories of these panelists and what they did to transform their workplace with actual genai success stories.”
As AI continues to evolve, one thing becomes clear. This is a technical leader who ignores the risk of delays. Cullen’s sessions help leaders get through the hype and take a practical, strategic approach to AI-powered leadership.
The Canadian CIO Association will be held in Ottawa from May 28th to 29th. Don’t miss out on the opportunity to hear from Cullen and other industry leaders shaping the future of IT leadership.
