3 questions leaders should ask any time they’re making changes

It’s widely reported that 70% of all change initiatives fail. Lindsey Caplan and Josh Levine offer a framework for making change stick.

3 questions leaders should ask any time they’re making changes
[Source image: Richard Drury/Getty Images]

“Our employee survey results just came back, and it says they aren’t feeling valued. We need to do…something.” Our client seemed to be at a loss. She was grasping for an answer. “We have a 2-day slot in June—can you help us pull an event together where we can do something fun with recognition?”


We’ve been getting a lot of questions about employee retention lately. After addressing modern employment basics like work flexibility and refreshed perks, many leaders are asking how they can improve their culture to increase loyalty.

Culture change is a huge undertaking. Even the best strategy or culture platform can get waylaid on the way from plan to execution. Whether increasing trust among colleagues or helping front-line staff improve the customer experience, changing behaviors is a big task for leaders and employees. On top of that, it’s widely reported that 70% of all change initiatives like these fail.

To improve the odds of launching and implementing a successful culture change program—one with results that last more than a single quarter, answer these three questions first. 


What do we want to be different?

It’s a common mistake for executives to begin the quest for change with the solution instead of the effect. When leaders jump too quickly to an answer—’better benefits!’ or ‘leadership off-site!’—they risk tiring staff and management with quick fixes that will likely fail. 

Implementing a program without knowing why is like hitting the accelerator ignorant of the destination—you’ll be moving, but probably in the wrong direction. What every culture change program needs first is clarity of intent.

The leader of any initiative must first determine an outcome. The answer to “what do we want to be different?” should be concise, concrete, and supported by the behaviors that drive that change. 


One recent example is from a B2B Fortune 500 financial services company whose CSAT scores had waned 15% over the past few years. Instead of starting with company-wide proclamations (the solution), they should clarify their intent first (the outcome). For them, an outcome statement might be, “To improve our customer satisfaction score by 10% in the next year, we need employees to understand our CX goals and their role in achieving them.” 

Here are a few questions to get you started if you want to redefine success:

  • What would this change mean for the business? 
  • What data can we cite to support this change effort? What will we be able to measure afterward to demonstrate the impact?
  • What do we need from the people we’re trying to affect? Why is that important?
  • How will we know we’ve succeeded? Will we be able to tell a before and after story?

What’s in it for employees?

Managers can issue mandates hoping to muscle employees into change, but lasting shifts in behavior only stick when people understand how it will benefit them personally. This strong desire to help oneself is why every culture change program must answer the question employees will inevitably ask: What’s in it for me? (What we call WIIFM, for short.) 


At a recent launch of new values at the DC Public Library, the organization’s executive director stood in front of a room of 80 leaders, describing the importance of the change. By enacting the values, he argued, the organization will improve how the staff works together and, in turn, be able to serve their community better. That is true, but only when the VP of HR stood to explain that she would be integrating these values into every staff member’s HR goals did these managers sit up a little straighter.

A higher aspiration like serving the customer is critical to light the spark of change, but to see it burn brightly beyond a few months, every employee must understand why it matters to them.

To uncover why employees should care about your change program, start by answering these questions:

  • What is being asked of employees, and how will this impact them?
  • How will the program change positively impact the employee’s day-to-day life?
  • How does this change connect to feedback employees have shared or business needs expressed?
  • What are examples of how a similar change has positively affected another team or respected organization? 

What could get in the way of the change we want?

After a concrete outcome is defined and employees know “WIIFM,” let’s talk about what could go wrong. Challenges constantly thwart even the best-prepared teams on the best-planned route. One way to overcome these roadblocks is to recognize and remove obstacles before they are a problem. After all, we can commit to eating healthier, but it’s a lot harder if there are Oreos in the pantry.

Good intentions are a start but not the solution. Some forces keep us stuck in the status quo even with the best intentions. Stanford professors and organizational psychologists Jeffrey Pfeffer and Bob Sutton coined the “Knowing-Doing Gap” to describe a maxim of change—knowing better doesn’t equal doing better. The good news is that the prepared leader can close this gap.

After some cajoling on our part, that client we mentioned above–the one who’s employees didn’t feel valued–realized a rah-rah “re-invigorate our employees” event in June might spur positive feelings for a few days, but the energy would dissipate. Old habits would inevitably re-emerge as stressed managers demanded individuals hit their quarterly numbers. Additionally, we found that those same managers lacked the mechanisms to formally reward their team more than the once-a-year promotion and review cycle. Lasting change meant removing these behavioral roadblocks.


Managers’ formal expectations now include providing rewards and recognition, and they are going to be measured on their team’s employee survey scores (a clear WIIFM). Furthermore, our client worked with her team to provide all leaders with the tools and skills they needed to start recognizing their employees more frequently, including training on the importance of positive feedback and recognition. We worked with our client to weave specific behavioral tweaks into the day-to-day rhythm vs the ra-ra of a one-and-done event.  

What challenges can you find and remove? Start here:

  • What existing systems or processes are at cross purposes with the desired change?
  • Who are my ‘blockers’—people who won’t be on my side unless included in the process?
  • What have we tried before, and why did that fail? And why did it succeed?
  • What skills, knowledge, or motivation may be lacking? 
  • What might inhibit or contradict this change in our current policies or practices?

Pain is a powerful impetus for change, particularly when caused by organizational issues like high turnover or poor survey results. We understand why these moments feel like crises and why we rush to take immediate action. Don’t. At least not before answering these three questions: What do we want to be different? What’s in it for employees? What could get in the way of the change we want? You’ll drastically improve your odds of creating lasting change by defining a concrete goal, fueling employee motivation, and gaining a clear view of the challenges that lie ahead.


Lindsey Caplan is a screenwriter turned organizational psychologist who helps HR and business leaders script their change efforts for the effect they want. Her forthcoming book, The Gathering Effect, is based on her research and consulting practice.

Josh Levine is a passionate advocate of all things company culture. He is the author of Great Mondays, one of BookAuthority’s best culture books of all time.