Product management is defined by its uncertain nature, where certainty is more an anomaly than the norm.
Demilade Olufayo, a seasoned Senior Product Manager, stands as an exemplar through his skilled manoeuvrability around uncertain scenarios, using a distinct integration of accuracy, vision, and sharp analysis.
With over a decade of experience creating consumer platforms as well as enterprise solutions, Demilade’s approach to making decisions in uncertain environments offers invaluable insight to product leaders operating in complex ecosystems.
Demilade bases his approach to uncertainty on the knowledge that end products are rarely ever a sure thing. He clarifies this concept by saying, “There is no such thing as a perfect input or a surefire result.”
Product decisions tend to lean on assumptions, shifts in the marketplace, and uncertain user actions.” Rather than chasing absolutes, he has established a culture that incorporates probabilistic analysis with rigorous scenario planning—a system that allows teams to chart through uncertainty without reliance on speculation or unjustified optimism.
Demilade bases his approach to uncertainty on the knowledge that end products are rarely ever a sure thing. He clarifies this concept by saying, “There is no such thing as a perfect input or a surefire result.”
At the centre of Demilade’s approach to making decisions lies the understanding that any hypothesis around a product has a built-in likelihood of coming true. As a result, every item on his roadmap, every feature release, and every request from customers should be considered a part of a distribution of probabilities, not separate estimates.
When he was working at his old company, when redesigning a central payments feature, Demilade didn’t restrict his attention to a typical user flow; he performed simulation that included edge cases, modes of failure, and unusual use cases.
Doing this didn’t only improve technical implementation but also eased communication to stakeholders, as he was able to present risk and uncertainty in an instructive way.
One of the more striking examples of this practice came early in a cross-functional growth project to enter a new country in Africa. With much excitement about potential revenue streams and share of market, Demilade was steadfast against pressure to make choices based on overly optimistic assumptions. Instead, he conducted a series of scenario-planning exercises in which he and his staff drew up contrasting futures based on differing regulatory reactions, infrastructure hurdles, and partnership risks.
They applied a range of probabilities to each scenario—not as a precise forecast of what might actually happen, but to light up the potential possibilities if their underlying assumptions were wrong, so that when a partner backed out of the project over compliance issues, he was unfazed by having already initiated execution of a mitigation plan developed weeks earlier.
At the centre of Demilade’s approach to making decisions lies the understanding that any hypothesis around a product has a built-in likelihood of coming true. As a result, every item on his roadmap, every feature release, and every request from customers should be considered a part of a distribution of probabilities, not separate estimates.
What sets Demilade apart isn’t what tools he uses, but how much effort he puts into using them. Probabilistic analysis, he believes, goes well beyond being a tool that analysts would use; it’s a state of mind that leaders of products would have to adopt to make unbiased decisions in environments where there isn’t complete information available.
He strongly urges his teams to measure how confident they are in projections, then change these estimates as more data comes along. Bayesian methods promote intellectual humility, allowing teams to change their minds rather than hanging onto obsolete beliefs.
Demilade has a deep understanding of the psychological force that uncertainty can have on teams. One of his lesser-known skills involves his ability to combine analytical rigor with empathetic insight. He admits that uncertainty can lead to stress, indecisiveness, or paralysis in team members. In meeting this challenge, he insists that scenario planning be used as an empowerment device, not an intimidating device.
When faced with a range of possible futures and an understanding of how actions map onto each of these futures, teams are more likely to feel empowered than daunted. Through this delicate balancing act between realism and determination, Demilade has earned respect from engineers, designers, executives, and customers alike.
Demilade has a deep understanding of the psychological force that uncertainty can have on teams. One of his lesser-known skills involves his ability to combine analytical rigor with empathetic insight.
His experience suggests that successful uncertainty management hinges not on avoiding risk but on managing it intelligently, watchfully, and cautiously. In areas where he is creating tools in-house for finance activities, assessing ideas dealing with user acquisition, or refining API integrations from partners, Demilade shows a composed attitude born from cautious optimism—never being passive or panicky.
As we continue to move into a more uncertain world, shaped by shifting consumer behaviours, macroeconomic disruptions, and fast-paced technology progress, critical thinking in uncharted arenas could become a hallmark of effective product leaders.
Demilade Olufayo’s piece acts as a reminder that certainty might be hard to come by, but clarity is possible; in fact, even in the most uncertain of circumstances, using the right tools, having a positive mindset, and practicing self-control, individuals can ultimately make brave, informed, and decisive choices.
