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25 Years of Leadership Lessons

Insight Experience turns 25 this year. That means we have spent a quarter century with an extraordinary opportunity to observe the pressures and rewards of corporate leadership and to learn from leaders across hundreds of clients.

Our business simulation experiences focus on leadership, not specific functional or industry skills. This gives us a unique vantage point. We dig in with clients across industries and markets about how they lead: how they make decisions under pressure, how they communicate during uncertainty, how they balance competing demands, and how they develop the people around them.

After 25 years, what have we learned?

We’ve learned a lot about what makes leaders successful and a lot about how organizations really work.

About Exceptional Leaders

1. Leading is about people and human skills first, business acumen and technical skills second.

This isn’t an either/or game. The leaders who excel understand that business acumen and technical expertise matter, but human skills are what separate good leaders from great ones.

The best leaders hone their ability to communicate clearly, read the room, judge talent, support and empower employees, and connect at a human level. They earn the trust of those around them and so gain loyalty and discretionary effort from their team. Human skills enable leaders to encourage their teams and hold them accountable, to create momentum and engagement, and to get through complex change.  

2. Tough empathy is the leader’s role.

Leaders do not make all the decisions in an organization, but they often have to make the most difficult ones.

They are the ones who have to “call the question” about a product, a project, or a person who is underperforming. Leaders set the timing for tough trade-offs and make the call even in the face of ambiguity. They set the priorities that others would rather avoid. Tough empathy takes courage. These decisions can be lonely ones.

The leaders who take this on with humility and human focus, who can be both decisive and empathetic, enable organizations to deliver results.

3. You can’t lead without reflection.

Every great leader we have met or worked with understands that perspective and learning take time. They don’t just push forward relentlessly. They pause to think.

They have myriad tools to carve out the time and the data to help them reflect: color-coded calendars, offsites, Monday morning planning sessions, end-of-week recaps, personal “operating models” that intentionally allocate their time across businesses, investments, and priorities.

Great leaders are intentional about stepping back. They know that without reflection, they’re just busy, not effective.

4. Great leaders are optimists.

The path to business success is filled with pitfalls and challenges and wrong turns. It’s hard and often discouraging work. The most effective leaders recognize that but bring an inherent sense of possibility and optimism to the work. They see the path to a different future. They continually remind their teams, their investors, their customers, and themselves about the why.

Optimism isn’t naïve. It’s the belief that the effort is worth it, even when the outcome is uncertain.

About Organizations

1. The middle of the organization is the propulsion system.

Senior leaders set direction. But unless they can mobilize the people architecting the work—the people who ensure products get built, contracts are signed, customer calls are answered—the business will not accelerate results or shift direction.

The middle of the organization is where strategy meets execution. It’s where translation happens. Leaders who neglect or underestimate this layer of the organization are perpetually frustrated by the gap between intent and results.

2. Great strategy is relative—to customers, to competition, to cost, and to time.

Leaders who overfocus internally lose their bearings.

Strategy isn’t developed in a vacuum. It’s shaped by what customers value, what competitors are doing, what resources are available, and what timing demands. The best leaders constantly scan the external environment. They adjust. Their thinking moves at the pace of the market, which often is not the pace of the organization. Effective leaders are aware of their assumptions and constantly testing their beliefs.

3. Benefiting from transformative technology is not additive. It requires letting go.

The current AI frenzy is reminiscent of other technological transformations we’ve observed, albeit at a broader scale. What did observing digitization teach us? What did observing the trend of reengineering help us understand? The lesson is the same: Realizing the benefits of new technology requires letting go of the old.

Increasing efficiency or productivity is just the beginning. The real questions are: What will your organization do with the capacity that the technology creates? What will you stop doing?

Unless there’s a plan for that new capacity—how you’ll reimagine processes or pursue new opportunities—the benefit of the new technology will be a fraction of what’s promised.

What’s Next?

Twenty-five years in, we’re still learning. Leaders continue to surprise us with their resilience, creativity, and capacity for growth. Organizations continue to challenge us with their complexity. We are so grateful for this opportunity to learn from them.

And we’re more convinced than ever that the best way to develop leaders is to give them a space to practice—to make decisions, experience consequences, receive feedback, and reflect—before the stakes are real.

Here’s to the next 25 years of learning together.

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