5-Are You Ready? A Leadership Perspective on Change Readiness

How Senior Leaders Know When Their Organization (and Themselves) Are Truly Ready for Change

Introduction: The Question No One Wants to Ask

Change is easy to talk about—until you have to make it real.

Whether you’re driving transformation across an organization or navigating a leadership shift within your own team, there’s always one uncomfortable, unspoken question:

"Are we actually ready for this?"

Not ready in the sense of having a project plan or a change management framework—those are mechanics. But ready in the sense that people will actually follow through, adapt, and sustain the change once the formal rollout is over.

Most change initiatives don’t fail because of bad strategy. They fail because the people responsible for making them successful weren’t psychologically, structurally, or culturally ready to commit.

So, how do senior leaders recognize whether readiness exists—or if they need to create it first?

Understanding the Layers of Readiness

When leaders think about readiness, they often focus on logistical preparation:

✔ Do we have the budget?

✔ Have we planned the rollout?

✔ Have we assigned the right people?

But those are just surface-level readiness checks. True readiness happens at a deeper level—the intersection of leadership clarity, organizational energy, and timing.

1-Readiness of Vision: Are You Clear on What This Change Really Requires?

Change doesn’t just require action—it requires clarity. Before assessing whether a team or organization is ready, a senior leader must first assess:

🔹 How strong is our definition of success? Is this change fully thought through, or are there still competing ideas of what “done” looks like?

🔹 Have we mapped what this vision actually requires? Beyond just tasks—what behaviors, decisions, and investments must shift?

🔹 Are we ready to defend this vision against pressure to dilute or change course?

🚦 Leadership Insight: If the vision isn’t clear, neither is the path forward. If you can’t describe the change concisely, the organization isn’t ready for it yet.

2-Readiness of Inputs: Do You Have What You Need to Sustain the Change?

Many change efforts start strong—then stall when reality sets in. Leaders are excited, teams are motivated, but somewhere along the way, the enthusiasm fades.

Why? Because the organization wasn’t equipped to sustain the momentum.

Ask yourself:

✔ Do we have the right talent and resources to make this change successful—not just to start it, but to carry it through?

✔ Have we mapped where friction will emerge? What processes, habits, or incentives are working against this change?

✔ Are leaders and teams truly committed, or are they just “on board” in theory?

🚦 Leadership Insight: Readiness isn’t about whether people say “yes” in meetings—it’s about whether they have the time, space, and support to follow through when the work gets hard.

3-Readiness of Timing: Is This the Right Moment?

Even the best change efforts can fail if the timing is off. If an organization is already dealing with instability, overload, or leadership uncertainty, a new initiative—no matter how strategic—can feel like an unwanted disruption.

Before moving forward, ask:

What else is happening right now? Are teams already overwhelmed, or is this a natural next step?
Is there energy for change, or are people just bracing for another “initiative of the year” that won’t last?
If we don’t do this now, what will change in 6 months? Are we acting out of urgency, or is this truly the right moment?

🚦 Leadership Insight: The right idea at the wrong time will still fail. Recognizing organizational bandwidth is just as important as recognizing strategic need.

Final Thought: Readiness is a Leadership Conversation

Senior leaders often feel pressure to push change forward, even when they sense resistance. But forcing a change that an organization isn’t ready for doesn’t create momentum—it creates disengagement.

Instead of asking, “How do we make this happen?”, start with:

What would make us feel truly ready for this?
Where do we still have uncertainty?
Are we setting ourselves up for real adoption, or just a well-documented rollout?

🚦 A leader’s job isn’t just to drive change—it’s to recognize when the conditions are right to make it stick.

This post is part of Maypop Grove’s Leadership Evolution Series—a collection of in-depth reflections on leadership, influence, and strategy. Designed for leaders navigating complexity, this series explores how to drive change, build resilient teams, and lead with confidence.

Learn more at maypopgrove.com or reach out to grow@maypopgrove.com.