
The lack of a shared, measurable definition of success has been a source of friction in the C-suite for years. Now, with AI investment on the rise, the problem is intensifying. Without a collective understanding of key milestones, leadership teams tend to focus on competing priorities. The result is an unintentional tug-of-war that can pull an organization's strategy in multiple directions at once.
For an expert's take, we spoke with Brian Tilzer, former EVP, Chief Digital, Analytics and Technology Officer at Best Buy, and the first Chief Digital Officer at CVS Health. As a senior executive who has navigated these challenges at the highest levels of the enterprise, he has a proven track record of leading large-scale digital transformations. But in a moment when AI dominates most leadership conversations, Tilzer is more interested in something else: clarity. For executive teams to succeed with big initiatives, he explained, they must first invest in the hard work of aligning on goals and the metrics that define them.
"AI might change how we execute, but it doesn’t change the fact that leaders must define, prioritize, and question what still differentiates us, and what’s now just the cost of doing business," Tilzer said. For him, this new era demands a different kind of C-suite—one fluent in data, relentless about alignment, and humble enough to recognize that human judgment remains the most complex system to scale.
Clarity is king: Most collaboration breakdowns come from leaders working with different definitions of 'good', Tilzer explained. "Success requires absolute clarity on your objectives and key results. When you can express those goals in measurable ways that everyone agrees on, you create the conditions to win."
Strategy isn’t a document on the shelf, he explained. It's a system of alignment. Without consistent language and metrics, even the most visionary goals get lost in translation.
This focus on human-led alignment gets to the heart of what Tilzer sees as a core obstacle for enterprise leaders in the AI era. While an algorithm can execute a task, it can't make a nuanced judgment call between multiple valid, competing strategies. That remains a uniquely human skill—and one that is now more valuable than ever.
The AI irony: Ironically, a focus on human-led alignment is where Tilzer identified another significant challenge for enterprise leaders. Algorithms can execute a task, but they can't make a nuanced judgment call between multiple valid, competing strategies. "The irony of the AI world is that the role of critical thinking and purposeful collaboration is more important than ever. The role of humanity in leadership is even more vital," he said.
The most successful enterprise leaders aren’t just evaluating, planning, or integrating AI, Tilzer continued. They’re thinking critically about what shouldn’t be automated, what trade-offs matter, and where humans still add unique value. From his perspective, the future ROI potential of enterprise AI will be defined by executives who ask the best questions and then apply that knowledge to their human-led and agent-led workflows.




