I cut my teeth getting grounded in principles of design thinking when I launched a strategic design MBA during my university teaching years. Design thinking is essentially a problem-solving process that is 50% qualitative research and 50% the application of design principles such as visualizing data and prototyping. In the design thinking world, we are well aware that 80% of the problem-solving process is grounded in making sure you even ask the right question . . . before you go running down the rabbit hole of possible solutions. All great problem-solving starts with identifying the actual problem to solve, which is discovered with really great questions.
That’s why a recent conversation with Jim Szafranski, CEO of Prezi, was affirming. He had learned the same lesson—twice—through an entirely different path. First, as an MIT graduate student in the late 1980s, applying early AI techniques in steel mill production. And again decades later, leading a global presentation platform, Prezi, into the age of generative AI. Both times, the breakthrough came not from better technology, but from asking a better question.
“The closer you are to what the ultimate point of what you’re doing is, the better,” he told me. At the steel mill, that meant shifting focus from machine efficiency to customer delivery timelines. At Prezi, it meant moving away from asking customers where they got stuck in the interface and to asking what they were actually trying to accomplish. The answer surprised Szafranski’s colleagues: “I have a deadline tomorrow. That’s my problem.” It had less to do with how pretty their deck was.
This is what I call the difference between optimizing and orienting. Most organizations are excellent at optimizing. They have dashboards, objectives and key results (OKRs), and retrospectives designed to make existing processes run faster and smoother. But orienting—stepping back to ask whether you’re climbing the right mountain in the first place—is far rarer and much more valuable.
Szafranski explained the research methods Prezi used to find its reframe. Early on, team members conducted granular user interviews about interface friction. That line of questioning was deeply useful for optimization but was limited for transformation. “That can keep you really focused on the trees sometimes, not the forest,” he reflected. The unlock came when they zoomed out to broad surveys asking about people’s goals, not their behaviors. Eventually, they made the question literal: Before users could even enter the product, they had to answer when their presentation was due.
This distinction—between improving your product and solving your customer’s actual problem—has profound implications for how leaders deploy artificial intelligence. The seduction of AI is its capacity for automation. But automation applied to the wrong problem is just elegant misdirection! Szafranski is candid about this risk: “Your job can be much higher level. Step back. Think of your customer, think of the outcome you’re trying to drive and they’re trying to drive.”
In my work as a creativity strategist, I see this pattern constantly. The leaders and organizations that thrive aren’t necessarily the ones with the most sophisticated tools, but rather the ones with the clearest view of purpose. They’ve done the inside-out work of understanding what problem they’re actually in the business of solving, so that every tool, every hire, every investment becomes purposeful rather than reactive.
Szafranski offers a practical heuristic for knowing when you’ve found the right problem: “If you can explain it over a dinner table with someone in your family who doesn’t really know what you do, then you’ve probably found the right problem.” I’d add my own corollary: If you can doodle it, you actually understand it.
The question worth sitting with this week isn’t whether your team is executing well. It’s whether you’re all pointed at the right target in the first place. The most powerful move a leader can make isn’t to hand their team better tools; it’s to help them ask better questions.
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