5 Critical Questions to Ask Before You Begin a Change Initiative

people holding papers of question marks in front of their faces.

You’ve identified the problem. You’ve found a potential solution—a new tool, process, or structure that could make a big impact. And you’re ready to lead your organization through change. 

But before you move forward, ask yourself this: 

Are you ready for change? And is your organization ready to follow you? 

Many change initiatives launch with energy and optimism—only to fizzle out weeks later. Not because the ideas were bad but because the groundwork wasn’t in place to support success. 

Before you roll out your next big initiative, take time to consider these five critical questions. Your answers could mean the difference between another failed change or one that truly drives improvement.

1. What Business Result Are You Trying to Achieve?

It’s tempting to implement change for the sake of progress—launching a new system, restructuring a team, or adding a new training program. But unless you’ve clearly defined the desired business outcome, your team may struggle to connect the change to anything meaningful. 

Jeff Chan recommends starting with a simple question: 

What is the business result we’re trying to achieve—financially, operationally, or from a customer experience perspective? 

When you define the end goal, it’s easier to assess whether the proposed change is the right one—and whether it’s worth the effort.

2. What Behaviors Need to Change?

Change doesn’t succeed because something new is introduced. It succeeds when people adopt new behaviors that lead to better outcomes. 

That means you need to be clear about what is expected. 

  • What are employees currently doing that needs to stop? 
  • What new habits, routines, or responsibilities will they need to start? 
  • Are those behaviors clearly tied to the business outcomes you want? 

If you can’t answer these questions, your team won’t be able to either.

3. Do We Have the Right People, Skills, and Support?

Even the best ideas fall flat if your team isn’t equipped to implement them. Before launching your change, consider: 

  • Do employees have the skills required for the new way of working? 
  • Do managers understand their role in leading the change? 
  • Is there support in place to guide people through the transition? 

Steve King points out that managers play four essential roles during change: proxy, communicator, coach, and advocate.  

If they’re not ready—or not brought in early—you may be setting them (and your change) up to fail.

4. How Will You Incentivize and Reinforce the Change?

Launching a change is only the beginning. People need reinforcement to stay the course—especially when the new way of working feels uncomfortable. 

Think about what incentives, recognition, and reinforcement mechanisms will keep momentum going. 

  • Will success be tied to performance goals? 
  • Will leaders celebrate small wins along the way? 
  • Will you continue to support the change after implementation? 

Without reinforcement, employees are likely to revert to the old way of doing things—even if the new way is better.

5. How Will You Know If It’s Working?

One of the most overlooked parts of change leadership is measuring success. Too often, leaders implement change and assume it’s working—only to discover months later that performance hasn’t improved. 

Before you launch your initiative, determine how you’ll track: 

  • Adoption: Are people doing the new behaviors? 
  • Outcomes: Are those behaviors producing the desired business results? 
  • Feedback: What’s working, what’s not, and what needs to be adjusted? 

Successful change leaders don’t just set and forget. They monitor, learn, and adjust along the way. 

Change That Sticks Starts with the Right Questions

Launching change without preparation is risky. But when you ask the right questions—before you begin—you set your team up for success. 

Whether you’re introducing a new system, rolling out a new process, or driving a strategic shift, thoughtful preparation can help your organization not just change but improve. 

The Change Management program gives leaders like you the tools to plan smarter, lead better, and achieve real results through change. You’ll learn how to engage your team, avoid common pitfalls, and create sustainable momentum—so change doesn’t just happen, it sticks.