Leadership in the Gray: Making the Call When the Path Is Unclear
Defining moments of leadership rarely arrive with perfect information and a reasonable timeline. The data is often incomplete and the timeline unclear. In those quiet moments before a decision is made and when clarity is elusive, a CEO must lean into sound judgment.
It is precisely at these moments that leaders are inspired to act, and the research confirms what many of us feel: decisiveness, not perfection, is often a distinguishing factor. The CEO Genome study, a decade-long analysis of thousands of executives, identified decisiveness —the capacity to make timely calls with imperfect information and course-correct quickly as new facts emerge—as one of four defining behaviors of successful leaders.
All organizations are now wrestling with the challenges and opportunities brought by agentic AI. The challenges are layered, and the opportunities are plentiful. For BBB National Programs, not only do we want and need to adjust our operations to a future of smart agents, but in this deregulatory environment, our organization must also paint that future as best navigated through the smart governance structures that can be brought by self-regulatory policies.
In my experience, progress sometimes depends on ensuring the organization keeps moving when the path forward is unclear. This is echoed by Amy Schoenthal in a recent article, which underscores that leaders must balance transparency with timely action to avoid both “analysis paralysis” and rash, reactive moves.
These questions aspire to narrow focus, reduce bias, and keep choices anchored in principle. But judgment is incomplete until it creates clarity for others.
Clarity is not the same as certainty. Certainty is rarely possible in ambiguous conditions; clarity is always required. Clarity comes from naming what matters most, explaining the principles guiding the decision, and showing the organization how progress will be measured.
I have found that good judgment is not only about what you decide but when you decide. Some choices demand urgency; others require thoughtful deliberation. What matters is that the pace matches the stakes. Teams respect urgency when urgency is required, as sometimes a campfire turns into a wildfire and needs immediate attention. Conversely, indecision disguised as process is a recipe for problems ahead.
As I have written previously, “An important measure of leadership is not in just predicting the future… but in guiding your organization and its people through change with confidence, attention to core values, a strategic mindset, business and financial acumen, clarity, decency, integrity…” That guidance means making decisions that reflect not only what is expedient, but what is aligned with your mission and values.
In my organization, I have found that clarity emerges from a few key disciplines. First, naming priorities openly so your team knows what takes precedence. Second, explaining the “why” behind major choices. And third, ensuring that decisions are not only heard but acted upon in a timely manner consistent with your organizational mission and values. Teams do not need every detail. They need to know where to focus their energy and how decisions connect to the larger mission.
Agentic AI is a striking example of how the process above can be helpful in addressing the challenges it brings. There should be no confusion over the what of your organization: it must be a priority to address agentic AI because (the why) the future will belong to those who get agentic AI right.
Again for us, the opportunities are twofold: navigating the “gray” to get agentic AI right as an employer and harnessing it to enhance the work we do, but also to drive engagement with our self-regulatory programs as they work (also in the gray) to address the larger societal issues brought by this technological leap.
Recent analysis by Dr. Cheryl Robinson argues that forced consensus leadership, while well-intentioned, tends to slow decision-making and water down ideas, especially when “lowest common denominator” choices may impede innovation. Leadership scholars likewise caution that forced consensus breeds groupthink and risk aversion, muffling dissent when it is needed most, some even calling it “the toxic enemy of creativity and innovation.”
Inclusion matters, but closure sometimes matters more. This does not mean leaders can ignore process. As Nitin Nohria, former dean of Harvard Business School, suggests, CEOs shape outcomes by designing the process, choosing when to engage, and then owning the call. The art is inclusion without paralysis, surfacing the best ideas while ensuring decisive closure.
The leaders who handle it best do not carry it alone; they sharpen their thinking with trusted sounding boards to strengthen judgment and build consistency, so when the decision is made, it carries both clarity and conviction.
In the end, leadership in the gray is about clarity of process, consistency of principle, and courage to act. Clarity provides direction. Consistency builds trust. And courage sustains progress when outcomes are uncertain, truer than ever in this age of agentic AI and deregulation.
It is precisely at these moments that leaders are inspired to act, and the research confirms what many of us feel: decisiveness, not perfection, is often a distinguishing factor. The CEO Genome study, a decade-long analysis of thousands of executives, identified decisiveness —the capacity to make timely calls with imperfect information and course-correct quickly as new facts emerge—as one of four defining behaviors of successful leaders.
All organizations are now wrestling with the challenges and opportunities brought by agentic AI. The challenges are layered, and the opportunities are plentiful. For BBB National Programs, not only do we want and need to adjust our operations to a future of smart agents, but in this deregulatory environment, our organization must also paint that future as best navigated through the smart governance structures that can be brought by self-regulatory policies.
In my experience, progress sometimes depends on ensuring the organization keeps moving when the path forward is unclear. This is echoed by Amy Schoenthal in a recent article, which underscores that leaders must balance transparency with timely action to avoid both “analysis paralysis” and rash, reactive moves.
Practicing Judgment in the Gray
Judgment is not instinct alone; it is a practice and a discipline. When facing ambiguity and a material decision, ask yourself: (1) What is the minimum I need to know to move forward? (2) Which of our values must guide this decision? And (3) If we are wrong, can we recover quickly and without significant financial impact on our organization?These questions aspire to narrow focus, reduce bias, and keep choices anchored in principle. But judgment is incomplete until it creates clarity for others.
Clarity is not the same as certainty. Certainty is rarely possible in ambiguous conditions; clarity is always required. Clarity comes from naming what matters most, explaining the principles guiding the decision, and showing the organization how progress will be measured.
I have found that good judgment is not only about what you decide but when you decide. Some choices demand urgency; others require thoughtful deliberation. What matters is that the pace matches the stakes. Teams respect urgency when urgency is required, as sometimes a campfire turns into a wildfire and needs immediate attention. Conversely, indecision disguised as process is a recipe for problems ahead.
As I have written previously, “An important measure of leadership is not in just predicting the future… but in guiding your organization and its people through change with confidence, attention to core values, a strategic mindset, business and financial acumen, clarity, decency, integrity…” That guidance means making decisions that reflect not only what is expedient, but what is aligned with your mission and values.
In my organization, I have found that clarity emerges from a few key disciplines. First, naming priorities openly so your team knows what takes precedence. Second, explaining the “why” behind major choices. And third, ensuring that decisions are not only heard but acted upon in a timely manner consistent with your organizational mission and values. Teams do not need every detail. They need to know where to focus their energy and how decisions connect to the larger mission.
Agentic AI is a striking example of how the process above can be helpful in addressing the challenges it brings. There should be no confusion over the what of your organization: it must be a priority to address agentic AI because (the why) the future will belong to those who get agentic AI right.
Again for us, the opportunities are twofold: navigating the “gray” to get agentic AI right as an employer and harnessing it to enhance the work we do, but also to drive engagement with our self-regulatory programs as they work (also in the gray) to address the larger societal issues brought by this technological leap.
Why CEO Decisions Often Cannot Be Crowdsourced
In today’s collaborative culture, it is tempting to seek input from every corner of the organization. And there is no doubt that listening is essential, as it has often opened my mind to many of the best ideas our organization has ever produced. But at the CEO level, decisions often cannot be crowdsourced.Recent analysis by Dr. Cheryl Robinson argues that forced consensus leadership, while well-intentioned, tends to slow decision-making and water down ideas, especially when “lowest common denominator” choices may impede innovation. Leadership scholars likewise caution that forced consensus breeds groupthink and risk aversion, muffling dissent when it is needed most, some even calling it “the toxic enemy of creativity and innovation.”
Inclusion matters, but closure sometimes matters more. This does not mean leaders can ignore process. As Nitin Nohria, former dean of Harvard Business School, suggests, CEOs shape outcomes by designing the process, choosing when to engage, and then owning the call. The art is inclusion without paralysis, surfacing the best ideas while ensuring decisive closure.
Clarity, Consistency, and Courage
Every CEO knows the weight of judgment. Decisions at the top shape strategy, culture, mission, reputation, and results. They affect people’s lives, and they are often made in solitude. The weight of that responsibility does not disappear when the meeting ends.The leaders who handle it best do not carry it alone; they sharpen their thinking with trusted sounding boards to strengthen judgment and build consistency, so when the decision is made, it carries both clarity and conviction.
In the end, leadership in the gray is about clarity of process, consistency of principle, and courage to act. Clarity provides direction. Consistency builds trust. And courage sustains progress when outcomes are uncertain, truer than ever in this age of agentic AI and deregulation.