Instead of waiting for a complete picture, courageous leaders take small, experimental actions to 'sense make' their way through ambiguity. This process, observed in emergency responders, involves acting, observing cues, and rapidly iterating. It is about learning by doing, not planning everything perfectly in advance.
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When facing ambiguity, the best strategy is not to wait for perfect information but to engage in "sense-making." This involves taking small, strategic actions, gathering data from them, and progressively building an understanding of the situation, rather than being paralyzed by analysis.
The best leaders act on incomplete information, understanding that 100% certainty is a myth that only exists in hindsight. The inability to decide amid ambiguity—choosing inaction—is a greater failure than making the wrong call.
Waiting for perfect data leads to paralysis. A core founder skill is making hard decisions with incomplete information. This 'founder gut' isn't innate; it's developed by studying the thought processes—not just the outcomes—of experienced entrepreneurs through masterminds, advisors, or podcasts.
To empower teams to act without perfect data, leaders must cultivate psychological safety. This means explicitly framing well-intentioned mistakes as acceptable risks. It encourages reps to trust their instincts and take necessary steps forward in gray areas.
Courage cannot be demanded or simply listed as a corporate value. A leader's key role is to be a 'context architect,' creating the organizational conditions for brave behavior. This includes allowing for failure, resourcing experimentation, and embodying courage personally, thereby enabling the entire organization to act bravely.
When faced with imperfect choices, treat the decision like a standardized test question: gather the best available information and choose the option you believe is the *most* correct, even if it's not perfect. This mindset accepts ambiguity and focuses on making the best possible choice in the moment.
To prepare for low-probability, high-impact events, leaders should resist the immediate urge to create action plans. Instead, they must first creatively explore "good, bad, and ugly" scenarios without the pressure for an immediate, concrete solution. This exploration phase is crucial for resilience.
Diller’s process for navigating the unknown isn't about brilliance but relentless iteration. He describes it as taking "one dumb step" at a time, bouncing off the walls of bad ideas and mistakes, and course-correcting. This embraces looking foolish as a prerequisite for finding the right path.
Inspired by Jeff Bezos's '70% rule,' modern creative leaders must be comfortable making decisions before having all the facts. In today's fast-paced media landscape, waiting for a perfect, 100% complete brief is a relic of the past. Agility requires acting on intuition and accepting that some details will be worked out along the way.
When strategic direction is unclear due to leadership changes, waiting for clarity leads to stagnation. The better approach is to create a draft plan with the explicit understanding it may be discarded. This provides a starting point for new leadership and maintains team momentum, so long as you are psychologically prepared to pivot.