Moving at the Speed of Discernment

In my previous article, "Hope Is Not a Strategy, But a Signal," I explored how hope can help leaders act with courage. But behind that idea lies a deeper and more complex reality that separates good leaders from great ones.

The real challenge is not only moving from hope to courage but also developing the discernment to know when bold action will serve the organization and when restraint will serve it better.

This is about strategic judgment in an era that often confuses motion with progress. And for many leaders, the struggle is not hesitation itself. It is the psychological conflict between the responsibility to move the business forward and the instinct to safeguard its stability.

The Complexity We Are Not Discussing

A seductive belief pervades much of business today, framing hesitation as weakness and speed as strength.

It is a narrative that plays out in leadership gatherings, meetings, and boardrooms every day—especially in the rush to adopt and maximize possibilities while understanding the realities of what executive decision-making demands.

Consider two contrasting leadership choices: One organization delayed a major product launch for several months because teams uncovered critical vulnerabilities. The pause prevented a costly recall that would have eroded trust and cost multiples of the investment cost. Another accelerated its digital transformation timeline by 18 months because leaders recognized that customer behavior had permanently shifted. This decisive move allowed them to capture market share that rivals have not regained.

Both required courage—one through restraint and the other through action.

What enabled both leaders to choose wisely was strategic discernment. This is the ability to differentiate between simple motion and meaningful movement. And this matters because the greatest risk in executive decision-making is not moving too slowly or too quickly. It is misdiagnosing the nature of the problem you are facing.

When Hesitation is Not Fear

Executive caution is often misunderstood when leaders pause for legitimate reasons that deserve attention. Here are some common instances:

1. Resource reality and constraints. Some leaders know exactly what must happen but recognize their organization lacks the capacity to execute well. Acting despite this creates unnecessary damage down the line.
2. Stakeholder complexity. Regulatory requirements, board expectations, and investor pressure are real constraints that require navigation, not defiance.
3. Information asymmetry. In technical or highly regulated environments, the cost of being wrong often exceeds the cost of delay.
4. Organizational readiness. Teams that are already stretched need stabilization before they can take on transformational change.

This is not soft. It is strategic.

Research confirms the impact of discernment; investment funds managing with long-term horizons generate extraordinary returns not through constant activity but through disciplined patience. Yale's endowment, for example, returned 9.5 percent annually over the decade ending June 2024, outperforming the median college endowment by 2.4 percentage points per year. The advantage includes waiting for the opportune time to maximize opportunities rather than yielding to pressure to deploy capital quarterly.

Discipline looks like hesitation to people addicted to motion.

The Action Bias Trap

In recent years, many leaders have embraced a version of the “move fast” mentality that has not always been productive. The belief that action is always superior to inaction reflects bias, not judgment. This action bias shows up in recognizable patterns, such as acting under pressure before the problem is understood or prioritizing visible initiatives over important foundational work. This overloads teams with shifting priorities and confuses rapid movement with actual progress.

The most successful leaders are not only more decisive but also selectively decisive. They calibrate their pace to the situation rather than their personal preference.

A Framework for Strategic Discernment

Leaders do not need to default to action or inaction but rather adopt a strategic position where they can evaluate decisions across three dimensions. This blends insights from the knowing gap with practical decision-making tools.

This also aligns with Snowden Cynefin’s sense-making framework, which states that in simple or complicated situations, analysis produces clarity and swift action creates value. While in complex situations, where cause and effect can only be seen in hindsight, experimentation outperforms premature certainty.

Urgent Versus Consequential

Many leadership missteps happen because the logic of a simple environment is applied to a complex one. But not all signals that demand attention require immediate action. Here are three factors to consider:

• Timing. What meaningfully changes if we wait 30, 60, or 90 days?
• Reversibility. Can we undo the choice(s) without significant cost?
• Impact. What are the long-term implications?

Leadership is the ability to reserve deliberate decision-making for irreversible and high-impact choices while moving quickly on opportunities that are reversible or time sensitive. Let’s expound on what this looks like for leaders daily:

1. Assess organizational capacity

Before adding more, assess what is already underway. Seek to understand the bandwidth of your teams and organizations by understanding the initiatives that are consuming the most energy. Similarly, understanding how much change the culture can absorb, and the recovery process required to fix a misstep.

This analysis is not designed to deter decision-making or make it easy to avoid making one because it is difficult; rather, it is about distinguishing between strategic load and destructive stress.

2. Design for learning

Strategic decision-making comes from experimentation—such that whether the leader acts or waits, the approach builds in learning.

When the call is one of action, building in adequate feedback loops and clear exit criteria ensures the learning. And if waiting, defining what new information would shift the decision ahead of time is powerful.

This turns both action and inaction into intentional experiments rather than instinctive choices. Research on organizational learning shows that sustainable success requires balancing the exploitation of current capabilities with the exploration of new possibilities. Both demand different time horizons and create value when matched to the right context.

3. Preparing for Recovery

Leadership stories often celebrate decisive moves and dramatic pivots. They rarely show the recovery work required when courage leads to unintended consequences.

The most effective leaders plan for success and for recovery. Before they act, they define what a productive failure looks like, identify the early warning signs, and outline an exit strategy. This allows the organization to respond quickly, maintain confidence, and turn mistakes into learning.

Resilient organizations are not those that avoid mistakes. They are the ones who recover quickly and convert them into capability.

The Paradoxical Nature of Leadership

What makes discernment difficult is that the landscape changes so frequently that a decision to wait today could require decisive action tomorrow. Understanding and embracing context—not personality—as a core driver of decision making.

F. Scott Fitzgerald wrote that the test of a first-rate intelligence is the ability to hold two opposing ideas at once and still function. This applies directly to leadership; great leaders are confident enough to act with incomplete information, humble enough to wait when patience serves better, and flexible enough to switch modes based on the moment rather than their instinctive preference.

Leadership is not a choice between hope and courage or between action and inaction. It is a yes and: the ability to know which one serves the moment and the capacity to execute that choice with conviction.

Boldness earns attention. Discernment earns trust.

And in a world that rewards speed, the real advantage belongs to the leader who matches their pace to the moment rather than to the noise around them.