JDR LEADERSHIP SERIES: Part 5 of 6
In today’s environment, leaders are not steering through clear lanes and predictable traffic. They are operating in dense fog at Formula 1 speeds. And the higher a leader climbs up the responsibility ladder, the denser the fog becomes.
The organizations that thrive are led by people who can move forward decisively when the stakes are high, uncertainty is the norm, the map is incomplete, and the competitive landscape keeps changing. This ability to successfully navigate the fog of ambiguity is one of the top 5 differentiating traits that separate the best leaders from the rest.
What navigating ambiguity really means
Navigating ambiguity is not about pretending to know more than you do or waiting passively for perfect clarity. It is the disciplined practice of creating enough direction to move while staying flexible enough to adapt as new information emerges. Leaders who do this well are comfortable making consequential decisions when cause-and-effect is murky and trade-offs are not clear because they lean into character and courage.
These leaders resist the very human impulse to force complex dilemmas into neat, binary choices (growth versus stability, centralization versus decentralization, speed versus quality) when the honest answer is that the organization needs some of both. They recognize that many of the tensions they face are not “problems to solve” once and for all, but ongoing polarities and paradoxes to navigate over time.
Why ambiguity is harder than ever
Ambiguity is not new, but its intensity and frequency have increased. Strategy cycles have shortened, technology is reshaping business models at an accelerating pace, and global shocks (e.g., pandemics, tariffs, and geopolitical events) regularly scramble assumptions. Leaders are asked to make “seemingly impossible” decisions in which every option carries operational, legal, reputational, and cultural risks.
Traditional planning approaches, which assume a relatively stable environment and linear cause-and-effect, tend to break down under these conditions. The attempt to engineer ambiguity out of the system with a highly detailed plan often backfires. The moment reality diverges from the plan, people either freeze or declare the plan a failure and revert to their comfort zone of firefighting. Successful leaders shift the goal from eliminating ambiguity to becoming better at living and leading dynamically within it.
Shifting from bipolar to nuanced
A core mindset shift is moving from an “either/or” view of complex issues to a “both/and” view. When leaders treat deep, enduring tensions as if they were simple problems, they tend to swing the organization from one extreme to the other, overcorrecting, then overcorrecting again.
Common examples include:
- Doubling down on “learning” and analysis until the organization drifts into paralysis, then lurching into “just build something,” only to discover that the solution is misaligned with customer needs.
- Over-indexing on centralization to gain control and efficiency, then swinging back to autonomy when responsiveness and innovation suffer.
- Pushing for rapid growth until systems strain, then slamming on the brakes to restore stability, losing momentum and credibility in the process.
Tools like Polarity Mapping help leaders and teams name these tensions explicitly, see the benefits and unintended consequences of what appear to be opposing solutions, and find a more nuanced win-win solution.
Asking smarter questions in the fog
Leaders who navigate ambiguity well spend less time defending their initial viewpoint and more time exploring the situation from multiple angles with a high level of curiosity. They also worry less about being the smartest person in the room and focus on bringing out the best in everyone.
When the path is unclear, the quality of a leader’s questions often matters more than the quality of their answers. One practical discipline is to resist asking “why” too early. In ambiguous situations, “why” can lure people into tidy explanations before they have done enough discovery.
Leaders are often better served by beginning with “what,” “who,” “when,” “where,” and “how” questions that surface surprises, exceptions, and weak signals that may point to an emerging threat or opportunity.
Research on strategic decision-making highlights several domains of questioning that are especially useful in ambiguous situations:
- Investigative questions (“What’s really going on?”) to surface missing data, assumptions, and constraints.
- Speculative questions (“What if…?” “What else…?”) to expand the range of options beyond the obvious first ideas.
- Interpretive questions (“So what?”) to connect facts and scenarios back to purpose, strategy, and values.
- Productive questions (“Now what?”) to stress-test execution capacity, sequencing, and resource requirements.
Leaders who underappreciate these types of questions are often blinded by their expertise or locked into familiar patterns that helped them succeed in the past. Consequently, they are more likely to overlook critical questions that could uncover obstacles before they become expensive surprises.
Planning as a verb, not a noun
In ambiguous environments, strategic planning must be treated as a verb. It should be an ongoing set of conversations and course corrections rather than a static document. As Dwight Eisenhower observed, the plan itself is less valuable than the planning process that fosters shared debate, context, and, eventually, alignment.
In ambiguity, the objective is not to engineer the perfect plan and then defend it. It is to strengthen the capacity of leaders and teams to keep planning as reality changes. Plan B is often just Plan A wearing different clothes, built on the same assumptions and blind spots. Strong leaders prepare for a broader range of contingencies, especially the less obvious and less comfortable ones, and they help their teams see course correction not as failure but as disciplined leadership.
An effective leadership approach:
- Uses planning to harness the collective intelligence and “constructive contention” of the organization, not to impose a top‑down answer.
- Focuses on critical questions: What do we value? What sets us apart? Where are we going? What does success look like? Where will we compete? What obstacles must we overcome? How will we win? What do our people need to perform at a higher level?
- Emphasizes connectedness and ownership: Every person should be able to answer, “How does my work help us win, and how do we define winning?”
- Executes the plan with excellence: Cascades accountability throughout the organization and promotes agile course correction based on fact-based learning.
This kind of planning and execution does not remove ambiguity, but it makes it more navigable by giving people a shared north star, a common language, and a framework for adjusting together as conditions change.
Practices of leaders who thrive in ambiguity
Leaders who consistently navigate ambiguity well dramatically reduce the odds of being blindsided or stuck. They practice the following behaviors:
▶︎ Accept ambiguity and embrace complexity instead of oversimplifying
They are willing to live with interim answers and evolving hypotheses, asking “What might be true here?” before jumping to “What is the answer?”
▶︎ Map tradeoffs explicitly
Rather than assessing operational, legal, reputational, and cultural risks in separate silos, they look at how these interact and document the trade-offs they are willing to make and why.
▶︎ Make reversible decisions quickly
When outcomes are uncertain, they prioritize moves that can be adjusted as new information emerges, preserving degrees of freedom while creating momentum.
▶︎ Test and use early warning indicators
They define leading signals that indicate when a chosen path is beginning to produce undesirable side effects.
▶︎ Invite diverse perspectives
They pull in voices from different functions, levels, outsiders, and backgrounds to see around corners and avoid being trapped by their own experience.
Leaders who thrive in ambiguity also avoid the trap of data dependency. They know that in a stable environment, more data often improves decision quality. But in fast-changing conditions, waiting for more information can produce hesitation, passivity, and drift. They look for meaningful signals early, interpret them carefully, and move at an appropriate pace rather than confusing delayed action with sound judgment.
Developing your “ambiguity muscle”
The ability to lead in ambiguity can be strengthened over time, much like courage or resilience. Leaders who want to grow in this area can take several concrete steps.
▶︎ Seek out ambiguous assignments
As Linda Hill notes in Rebecca Knight’s article 8 Essential Qualities of Successful Leaders, “Mostly we learn from our experiences and facing adversity. Stepping outside of the spaces where we feel safe — is a powerful teacher.”
▶︎ Reframe dilemmas as polarities
When you encounter a recurring tug-of-war—speed vs. quality, efficiency vs. innovation—pause and ask, “Is this a problem to solve or a polarity with greyness to navigate?” Then use a tool like Polarity Mapping with your team.
▶︎ Build a questioning habit
In key meetings, discipline yourself to ask at least one investigative, one speculative, one interpretive, and one productive question. Over time, this rewires your default approach from answer‑giving to seeking first to understand.
▶︎ Strengthen reflection routines
After major decisions or strategy cycles, conduct structured after‑action reviews: What did we assume? What actually happened? What signals did we miss? What will we do differently next time?
Ambiguity is not going away. The leaders who will be most valuable in the years ahead are those who can keep their teams rowing in rhythm and in the same direction even when the destination is still coming into focus. By shifting from either/or to both/and, from static plans to living planning, and from having answers to asking smarter questions, leaders can transform ambiguity from a source of anxiety into a competitive advantage.
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Scrappy and Relentless:
Why Ownership Mindset Beats Talent Over Time
Leaders with a scrappy ownership mindset do more than keep the lights on in turbulent times. They create cultures where people show up like owners, learn from adversity, and push and pull one another to achieve more than they thought possible.
In an era increasingly defined by disruption and uncertainty, that combination may be the most reliable competitive advantage a leader can build.
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