The Most Underrated Leadership Question: “Why Now?”

Severin Sorensen
59 minutes ago
6 min read

In boardrooms and team huddles across the globe, leaders are constantly peppered with questions: What’s the strategy? Who’s responsible? How will we measure success? But there’s one question that often goes unasked—yet carries the power to sharpen focus, surface urgency, and align an entire organization:

“Why now?”

This deceptively simple query acts as a time-sensitive lens into the motivations, risks, and consequences of action—or inaction. It can help leaders cut through noise, prioritize with clarity, and drive transformational change. Yet, its quiet power is frequently overlooked.

And the research backs this up. Studies show that urgency—real or perceived—can distort decision-making. We’re hardwired to gravitate toward tasks that feel pressing, even when they’re less important (Zhu, Yang, & Hsee, 2018). Emotional triggers like anxiety or uncertainty can push leaders to act fast instead of wisely (Lerner et al., 2015). And without reflection, urgency can override strategy, trapping executives in a cycle of reaction rather than intentional leadership (Santos, 2022).

That’s why “Why now?” is more than a scheduling question—it’s a cognitive circuit breaker.

Let’s explore why this underrated question deserves a central role in modern leadership—and how executive coaches, CEOs, and business leaders can use it to unlock insight, urgency, and momentum with clarity and purpose.

The Strategic Power of Timing

At the heart of the “Why now?” question lies timing—a factor that can determine whether a decision is visionary or reckless, necessary or premature. In leadership, timing is not just about schedules and deadlines. It’s about context: external market shifts, internal readiness, resource alignment, and opportunity cost.

Think of any bold organizational move—launching a product, restructuring a team, entering a new market, hiring an executive. The decision is never made in a vacuum. It lives inside a specific moment in time. And that moment deserves interrogation.

“Why now?” forces leaders to articulate what has changed, what is at stake, and what windows may be closing—or opening.

“If not now, when? If not you, who?” is a rallying cry. But “Why now?” is its wiser, more introspective sibling.

“Why Now?” and the Psychology of Urgency

Urgency can be a double-edged sword. It creates momentum—but it can also trigger anxiety, short-termism, and reactivity. That’s where “Why now?” becomes a powerful moderating force. Instead of reacting to pressure, leaders who ask “Why now?” learn to distinguish between:

True urgency: Is there a real-time risk or opportunity that demands action?
False urgency: Is this a distraction disguised as importance?
Manufactured urgency: Are we creating pressure to mask deeper uncertainty or avoid conflict?

This aligns with what researchers call the mere urgency effect—a cognitive bias where individuals prioritize tasks with time pressure over more important ones that lack deadlines, even when the latter offer greater value (Zhu, Yang, & Hsee, 2018).

By slowing down to ask the question, leaders actually speed up decision quality. They move from impulse to intention. Without this pause, leaders risk falling into the urgency trap—where constant reactivity suppresses critical thinking and prevents long-term strategic insight (Santos, 2022).

This is especially vital in change management. Leaders often rush into transformation projects, digital initiatives, or cultural pivots without building a clear rationale for “why now” is the moment. Asking “Why now?” helps anchor the narrative in reality and invites buy-in from those asked to change.

Change Management: The Missing Anchor

Change fails when people don’t understand its purpose or timing. “Why now?” becomes the anchor for both. When coaching executives through change leadership, this question:

Reveals the case for change beyond superficial metrics.
Encourages leaders to share personal conviction, not just corporate slides.
Helps teams see not just what’s changing, but why it must happen now.

For example, a CEO leading a merger might say, “We’re doing this to scale.” But why now? Perhaps competitors are consolidating, or the cost of capital is low, or key talent is at risk of walking. Stating this explicitly shifts the change from abstract strategy to lived urgency.

Coaching opportunity: Help leaders craft a “Why now?” story they can share repeatedly. When urgency is clear, resistance softens.

Prioritization and Trade-offs: The Hidden Cost of Yes

Every “yes” is a “no” to something else. “Why now?” brings these trade-offs into the light. In a world of competing priorities, leaders are bombarded with good ideas, urgent requests, and stakeholder expectations. But not all “important” things are “important now.” By asking “Why now?” leaders can:

Filter out noise and focus on high-leverage actions.
Avoid shiny-object syndrome.
Sequence initiatives for sustainability, not burnout.

This is especially relevant for high-performing executives who struggle with overcommitment. Everything feels urgent. But not everything is. “Why now?” is the gatekeeper that prevents the tyranny of the immediate from derailing the essential.

The Coach’s Role: Using “Why Now?” as a Reflective Tool

Executive coaches can wield “Why now?” as a scalpel, cutting through assumptions, revealing deeper truths. Here’s how to use it with intention:

In career inflection points: When a leader is considering a big move or shift—ask why this moment matters. What’s changed? What’s calling?
In values alignment: Why is this decision aligned with who you are becoming now—not just who you were?
In organizational coaching: Why is this team ready now? What is different in the environment, culture, or readiness?

Importantly, “Why now?” is not just about challenge—it’s about curiosity. When asked with genuine interest, it invites reflection rather than defensiveness. “Why now?” isn’t accusatory. It’s an invitation to get honest about timing, motivation, and meaning.

As research in behavioral ethics and decision-making suggests, having a reflective pause—like asking “Why now?”—helps leaders recognize their blind spots and ensure actions align with values and strategic goals (Bazerman & Tenbrunsel, 2011).

“Why Now?” in Times of Crisis

In crises, decisions accelerate. But so does confusion. “Why now?” helps leaders pause long enough to:

Distinguish between noise and signal.
Act with clarity, not fear.
Align the team around shared imperatives.

For example, during COVID-19, many companies pivoted business models, remote operations, or digital channels. Some made reactive choices that proved costly. Others asked “Why now?” and uncovered real needs—employee safety, customer access, business continuity. This led to intentional innovation rather than panic-based pivots. In wartime decision-making, urgency is non-negotiable—but so is clarity. “Why now?” is a battlefield filter.

The Organizational “Why Now?” Audit

To make this a practical tool, consider encouraging executives to run a “Why Now?” audit across your leadership portfolio:

Current initiatives: Why are we doing this now? What would happen if we delayed 6 months? What if we’d done it 6 months ago?
Cultural shifts: What’s making this moment ripe for change?
Team structure: Why are we reorganizing now? What has changed in the environment or team maturity?
Personal development: Why am I pursuing this growth now? What season am I in?

Red Flags: When Leaders Avoid the “Why Now?” Question

Sometimes, leaders resist this question—and that’s a signal. Avoidance of “Why now?” often signals a lack of clarity, courage, or conviction. And that’s where executive coaching can be a mirror. Here are some common red flags:

Vague urgency: “It just feels like the right time.” (Based on what?)
External pressure: “Everyone else is doing it.” (Is it right for us?)
Emotional reaction: “I’m just tired of this.” (Is this burnout or strategic clarity?)
Fear of missing out: “We’ll be left behind if we don’t act.” (By whom? At what cost?)

Instead of reacting to pressure, leaders who ask “Why now?” learn to slow the pace of urgency-driven decision-making.

Emotions play a crucial role here. Studies show that heightened emotional states—like anxiety or fear—can distort our perception of urgency, prompting us to act quickly to alleviate discomfort rather than assess importance rationally (Lerner, Li, Valdesolo, & Kassam, 2015).

Making “Why Now?” a Leadership Reflex

In an age of acceleration, where everything seems urgent, leaders must develop the skill to slow down just long enough to ask better questions. “Why now?” is one of the most underrated, underused, and high-impact questions a leader can ask. It’s the question behind:

Every smart strategy.
Every sustainable change.
Every courageous pivot.
Every purposeful “yes”—and every liberating “no.”

For executive coaches, “Why now?” is a diagnostic tool. For CEOs, it’s a strategic anchor. For all leaders, it’s a compass.

Start Asking “Why Now?” Today

During a meeting, when a decision is on the table, ask: “Why is this the right moment?”
Reflect on current projects: “What’s made this urgent now?”
Journal current goals: “What’s pushing me—and what’s pulling me—into this season?”

You may find that this one question changes everything.

References

Bazerman, M. H., & Tenbrunsel, A. E. (2011). Blind spots: Why we fail to do what’s right and what to do about it. Princeton University Press.

Lerner, J. S., Li, Y., Valdesolo, P., & Kassam, K. S. (2015). Emotion and decision making. Annual Review of Psychology, 66, 799–823. https://doi.org/10.1146/annurev-psych-010213-115043

Santos, S. (2022, December 2). Critical Thinking and the Urgency Trap | Harvard Business. Harvard Business Publishing. https://www.harvardbusiness.org/to-improve-critical-thinking-dont-fall-into-the-urgency-trap/

Zhu, M., Yang, A. X., & Hsee, C. K. (2018). The mere urgency effect. Journal of Consumer Research, 45(3), 673–690. https://doi.org/10.1093/jcr/ucy012