The Three Levels of Continuous Improvement Every Leader Should Master
“We build up these biases around certain things that are not possible or we can't do because of whatever the reasons are and if you label those things, that's an invisible rule.”
John Harrison, President and General Manager, WebMD Health Services:
In November, I spoke with two thoughtful leaders about their experience navigating high-stakes role transitions: John Harrison, President and General Manager at WebMD Health Services, and Yariv Hasar, President NA at Sapiens. Both reflected deeply on a central leadership question John posed:
“How do you constantly challenge yourself and how do you constantly challenge your peers in the organization, those that are a part of your team, to continually be looking for new and different ways to be better and to never be really satisfied with where we are?”
Across our conversations, a clear pattern emerged. Continuous improvement does not happen in one place. It shows up at three levels:
in how leaders reflect individually,
in how teams examine assumptions together, and
in how organizations listen and learn at scale.
Before I examine those more closely, I’d like to first offer a definition of “continuous improvement” as it relates to growth.
Continuous improvement is the act of reflection on the past, evaluation of the present, and adaptation for the future.
With that definition as the backdrop, let’s explore the three levels where continuous improvement surfaces.
1. Improving Individually: Reflection as a Daily and Annual Practice
Both leaders I interviewed use their calendars not only as scheduling tools, but also as devices for reflection and priority-setting.
Yariv relies on a daily reflection ritual. At the end of each day, he scans his calendar and asks himself:
“What did I do from the morning till day? Did I move the needle? Where did I move the needle? What have I done?”
Yariv shares that it’s not just about the achievements from the day, but how the day was spent:
“Did I set the right priority about meetings? Should those meetings have taken place now, or maybe I should have prioritized something more important than that?”
For Yariv, this is less about the completed tasks and more about how time was invested.
John takes a broader, structural approach. At the end of every year, he deletes every meeting he owns and rebuilds his calendar from scratch:
“I will delete every single meeting that I own, and I force myself to reschedule and think through what are the meetings that I actually should be having and want to have?”
Both view these practices as essential techniques for continuous improvement.
Whether in daily micro-reflections or annual resets, leaders grow when they challenge their habits and intentionally redirect their time.
2. Improving Together: Challenging Team Assumptions
At the team level, both leaders emphasized the importance of challenging beliefs and assumptions that constrain how people think and work together.
John uses the concept of “invisible rules” to describe limiting beliefs:
“We build up these biases around certain things that are not possible or we can't do because of whatever the reasons are and if you label those things, that's an invisible rule.”
John shares that “if you can continually challenge yourself on that thinking, what it does is it breaks your barriers.”
Yariv discussed the power of checking his own assumptions when working with teams to update practices. When he saw gaps in cross-team collaboration for example, he brought folks together. However, at the outset, Yariv explained that “I thought that I knew the answer, because I had more experience in delivery” but through discussion:
“We came up with a somewhat different…flavor or variant of what I had in mind and if we were not doing this dialogue and opening, giving it as an open question, perhaps we would have settled to my, I would say, pre-designed solution, which is not necessarily the ideal.”
Teams improve when they are invited to challenge the “invisible rules” that quietly shape behavior, and leaders improve when they promote team input. In these ways, dialogue becomes a mechanism for discovery.
3. Improving the System: Listening Widely and Learning Collectively
At the organizational level, both leaders use structured listening to reveal patterns and guide improvement.
John uses the Start–Stop–Continue method to gather broad input sharing that one can “do that not only at an individual level, but at a team or an organization level.”
“So, if you were to, again, to pulse your team when you come in and say, what are the top two things we should start doing? What are the top two things we should stop doing? What are the top two things we should continue doing? And if you do that across a broad enough part of the organization, there will be thematic elements that are truths.”
With regard to this practice, John shared that:
“You want to be open to hearing those things, and not be biased just by the four people that tell you what those things are, that there's more to learn from the rest of the organization.”
For him, organizational learning depends on hearing from many voices.
Similarly, Yariv emphasizes wide-ranging dialogue to decide what “good” looks like by hearing from the organization and beyond:
“Spend some time with your peers, with your bosses, colleagues, board even, and of course, customer, [on] what good looks like? Where are the things that you would like to change and where are the things that you would like to maintain.”
Organizations improve when leaders create structured ways to hear from many people, identify patterns that impact the organization and build shared clarity about where to adapt and where to stay the course.
Continuous Improvement as a Leadership Habit
Across these conversations, the core theme was unmistakable: Continuous improvement is a force accelerant to better outcomes when it is treated as a deliberate practice.
Leaders cultivate it by:
Consistently examining how they spend their own time
Openly inviting challenge to assumptions about how things should be
Inviting broad input to update understanding of the system
Or, as John put it:
“Never be really satisfied with where we are.”
Thinking about implementing a practice of continuous improvement within your own organization? It doesn’t need to be over-engineered. In fact, as John and Yariv made clear, the most meaningful shifts often come from simple, repeatable habits.
Both leaders show that improvement happens when leaders repeatedly ask: What should change? What should stay? And how do we get better from here?
If you’re looking for a place to begin, I recommend you start small. Pick one habit that helps you see most clearly, about yourself, your team, or your organization. Then practice it regularly and deliberately. Over time, these small moments of clarity compound into a culture that refuses to settle, evolves with purpose, and stays aligned around what matters most.
In the end, continuous improvement is less about perfection and more about movement. Movement toward better questions, better conversations, and better decisions. The leaders who develop this practice aren’t waiting for the right conditions. They are intentionally creating them. Every day.
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