Derek Cullen has spent years making the case for new technology. As Chief Information Officer at Stikeman Elliott, he’s led cloud migrations, cybersecurity program implementations, and digital transformation initiatives. But AI is different.
“This is the first technology project in my nine years here where instead of me going to the board like I did with cloud and saying this is why we want to go cloud, the board is coming to me and saying, ‘How do we get this done?’” Cullen said in an interview with Digital Journal. “We want to be there. This is transformational. We want to quick to market in the use of GenAI in professional services, and not last. We want to be prepared for this because it’s coming.”
That shift — from CIOs pushing technology to the CEO’s, chair, or board pulling for it — signals a turning point. AI isn’t just another tool. It’s changing how leaders think about technology’s role in business.
Cullen will explore this transformation at the CIO Association of Canada’s Peer Forum, where he’s moderating a panel on AI-augmented leadership. The discussion will focus on how CIOs can integrate GenAI into their decision-making and business strategies, navigating both its potential and its risks.
The balance of AI as a tool and a transformation driver
For Cullen, AI isn’t just another software upgrade. It’s a fundamental shift in how technology leaders operate.
He argues that it’s important to ensure AI is a key part of your toolkit. At the same time, leaders need to address every aspect of AI implementation across their organization, whether it’s risk, business transformation, or other critical areas.
Cullen sees AI reshaping workflows in two key ways:
- Enhancing productivity: Automating repetitive back-office tasks, in areas like finance operations, business development, and marketing.
- Transforming service delivery: Shifting how law firms, banks, and enterprises perform research and potentially produce work product.
But while AI can drive efficiency, Cullen warns against rushing in without a clear plan. He notes that with so many players in the AI space, much of the technology has yet to become standardized or fully tested.
“Some of it is encapsulated with a lot of hype still,” he says. Without proper vetting, organizations risk being disappointed by inflated expectations. “If your executives are asking you to get to the finish line, it needs to be very clear that there should be an assumption that some of this is hype and fiction until you’ve actually tested it and proven your use cases.”
He also points to the complexity of AI integration as a barrier many underestimate. While executives may expect immediate results, the reality is far more intricate.
“An executive might say, ‘I would like a GenAI solution to field a query to go through all of the last 50 deals we’ve worked on that involved Real Estate transactions and draft me an RFP response for a new deal, with the correct Lawyer bios with matching experience, and the pricing based on historical data that should win us this deal. In many environments that would involve the GenAI [needing access] to potentially over a dozen data sources. That is a major endeavour.”
Many executives now understand that these types of GenAI solutions predicate that data is in place, available and accurate and that the integrations themselves require careful thought and work.
Balancing innovation and risk
As a technology leader in a law firm, Cullen approaches AI with an additional layer of caution — particularly when it comes to client data. While AI can enhance productivity in back-office operations, its use in legal work requires a more measured approach.
“Law firms and our clients are very risk-averse so, it’s a bit of a delicate tightrope we’re walking right now,” he explains. “It’s an exploratory approach so that we understand the technologies, we try them out, we pilot, and plan for the applicable use cases.”
Cullen says his firm is proceeding with cautious optimism waiting to fully understand AI’s risks and rewards.
That tension between AI’s efficiency and the legal industry’s need for precision reflects a broader challenge facing CIOs. As AI becomes embedded in more enterprise tools, leaders must balance automation with accountability.
“You may think that they’re not training on your models. You may think they’re not using your data. Sometimes they are,” Cullen warns. “Being very careful about what you’re doing with your data and your IP is super important.”
Even with legal expertise in-house, AI’s contractual risks can be daunting.
“We’re a law firm, and it still takes us time to review the terms and conditions of AI vendors,” he says. “You may think you understand what you’re signing up for, but sometimes the fine print tells a different story. We’ve had to be extremely cautious about ensuring our data remains protected.”
What to expect from Cullen’s panel at Peer Forum
For technology leaders still unsure about AI’s role in leadership, Cullen’s panel at the CIO Peer Forum will provide concrete insights from technology executives who have already integrated AI into their strategies.
“What I’m hoping people take away from this is hearing the success stories of these panellists and what they’ve done to transform their workplaces with real GenAI success stories.”
As AI continues to evolve, one thing is clear: technology leaders who ignore it risk falling behind. Cullen’s session will help leaders cut through the hype and take a practical, strategic approach to AI-powered leadership.
The CIO Association of Canada’s Peer Forum takes place May 28-29 in Ottawa. Don’t miss the opportunity to hear from Cullen and other industry leaders shaping the future of IT leadership.
