What Rising Through the Ranks to CEO Taught Me About Leadership at Any Scale

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Key Takeaways

Empathy, adaptability and strategic foresight are essential for success, regardless of company size.

I’ve spent my career straddling the structured discipline of Fortune 500 companies and the entrepreneurial scrappiness of startups. Each side has its strengths. Startups move fast, fueled by creativity and urgency. Corporations scale big, built on systems and predictability.

But the future of leadership belongs to those who can bridge the two; leaders who think like founders and lead like CEOs.

Entrepreneurial leadership is the ability to remain agile and curious, like a founder, while maintaining the foresight and operational discipline of a seasoned executive. In an era of constant disruption, that combination is essential.

Treat failure like fuel

In many large organizations, failure is something to be managed rather than embraced. Metrics, quarterly targets and brand reputation often leave little room for experimentation. It’s safe, but that risk aversion can quietly stifle innovation.

Early in my career, I helped lead a new product launch that didn’t go as planned. We had done the research, built the plan and executed flawlessly (at least on paper). The market proved otherwise.

Instead of hiding from it, I brought the team together for an honest conversation about what went wrong. No finger-pointing. Just learning. That meeting changed how we worked. We began running smaller pilots, collecting feedback faster and rewarding curiosity over perfection.

Startups already know that every setback serves as important data. The difference between stagnation and growth often comes down to how quickly you can turn lessons into next steps. I tell executives all the time that failure isn’t fatal, complacency is.

Build “safe havens” for experimentation

Big companies talk about innovation endlessly. It sounds nice until you realize most innovation can’t survive big bureaucracy. Efficiency cultures tend to sideline creativity.

That’s why I believe in building “safe havens” for experimentation: small, cross-functional teams that operate with a startup mentality but have access to corporate resources. Their mission must be decoupled from immediate ROI. You want them to test, learn and translate what works back into the core business.

When I led a major retailer, we created one of these protected spaces for finding new product lines. The team experimented with a variety of product lines that at one point were considered to be very risky and not on-brand. Within a few short months, they identified several that were ready to roll out more broadly. It was a combination of quick wins, quick failure, and keen listening to customer feedback.

Innovation needs freedom before it can be scaled. You must permit your people to experiment and even fail if you expect them to create anything truly new.

Lead better by listening first

Leadership starts with listening. When I stepped into a new CEO role, I made a point to visit as many stores and offices as possible within my first 60 days. At one location, a front-line associate told me something I’ll never forget: “Our customers don’t just want faster service; they want to feel acknowledged and known.”

That important insight helped reframe our customer strategy. We moved from chasing speed to deepening connection.

It’s easy, especially when you’re expected to have all the answers, to fall into the trap of talking more than you listen. However, wise entrepreneurs know that every conversation holds valuable insights. Every customer complaint, every employee frustration, every quiet observation is a clue to your next opportunity.

Good leaders have mastered their business. The best are curious about the people who make it work.

Transform your dream into a scalable reality

Founders dream big. CEOs make those dreams scalable. Vision is essential, but without discipline, your vision is just a pretty picture.

I’ve worked with startups that burned out because they grew without structure. I’ve also seen established companies lose relevance because they clung to structure and forgot how to dream.

Today’s leaders must understand that speed doesn’t have to mean chaos, and structure doesn’t have to mean rigidity.

Entrepreneurial leadership is about knowing when to loosen the reins and when to tighten them. It’s the art of building systems that empower creativity rather than constrain it. When you strike that balance, you create organizations that can move quickly and remain resilient.

Lead with purpose, not ego

As a leader, it’s often better to be a big megaphone than a big voice. When important decisions need to be made, when you’re brainstorming the perfect strategy, use your position to amplify the right voices in the room.

In retail and consumer businesses, I learned early that people don’t just work for paychecks; they work for purpose. They want to believe their work matters. When you align people around a shared mission, productivity, engagement, and even profitability improve.

During a major transformation effort, I made it a habit to meet weekly with cross-functional teams to discuss progress and address challenges. We did the stock-standard numbers review, but I also wanted to hear what inspired or frustrated them. Those conversations surfaced insights that no spreadsheet could ever provide.

Over time, I realized that transparency builds more loyalty than perfection ever could. When things go wrong, own it. When people succeed, share the credit.

The best leaders replace ego with empathy. The result is trust, the most powerful currency in business.

Reinvent before you’re forced to

Markets change. Technology evolves. Consumer expectations shift. The question isn’t if you’ll need to reinvent, it’s when.

I’ve seen companies wait too long to evolve, convinced that past success guarantees future relevance. It never does.

Whether you’re running a startup or an established brand, you have to build reinvention into your DNA. That means constantly scanning the horizon, questioning your assumptions and staying hungry to improve.

One of the lessons I’ve learned is that transformation demands a continuous posture of adaptability. The moment you think you’ve figured it all out, you’ve already fallen behind.

The new definition of leadership

Entrepreneurial leadership doesn’t care about titles or hierarchy. The entrepreneurs I’ve seen thrive have a different mindset.

They think like a founder by being bold, curious and customer-obsessed. They lead like a CEO through disciplined, strategic, and people-centered practices. The leaders who can merge those worlds will shape the next generation of business.

Because success isn’t final, and failure isn’t fatal. What matters most is the courage to keep learning and the humility to keep evolving.