Grandpa Day

Leadership Lessons from Grandpa Day

How mentoring grandchildren shaped the way I think about leadership

One Saturday morning my three-year-old grandson Felix and I were sitting near the runway at Santa Monica Airport watching small planes take off. Felix carefully studied every step the pilots took before departure. “They check everything before they go,” he said. After decades leading and exiting multiple companies as a CEO, I realized the same lesson applied in business. Preparation, attention, and curiosity often determine whether a journey succeeds or fails.

Experiences like this eventually inspired what our family now calls “Grandpa Days,” intentional one-on-one outings with each grandchild designed to explore their interests and spend uninterrupted time together. These experiences became the foundation for my book Grandpa Day: Nurturing Grit, Smarts, and Love in the Next Generation. Unexpectedly, those simple outings revealed something else. Many of the lessons that help a child grow into a confident adult are the same principles that help leaders build strong organizations.

Different setting. Same framework.

Presence Is the Foundation of Leadership

Children notice immediately whether you are truly present.

One morning during breakfast, my granddaughter Serena paused mid-sentence and said, “Grandpa, you never look at your phone when I’m talking.” I had not realized she was paying that close attention. But she was right. When we spend time together, my phone stays in my pocket unless we are taking photos.

Employees notice the same thing. Leaders who are fully present build trust. Trust builds confidence. And confidence allows people to take initiative. In families we call this love. In organizations we call it culture. But the underlying principle is identical.

Curiosity Drives Growth

Children ask endless questions, and that curiosity should be encouraged.

Felix’s fascination with airplanes quickly turned into regular airport visits. He wanted to know how planes worked, why pilots performed certain checks, and what made each aircraft different. Those questions became our shared learning experience.

My granddaughter Serena’s curiosity took a different direction, eventually leading to a passion for craft chocolate and entrepreneurship. What began as a simple interest during our Grandpa Days grew into a deeper exploration of the craft chocolate world. The most innovative companies operate the same way. They are built by people who remain curious and constantly ask better questions. Organizations stagnate when curiosity disappears.

Praise Effort, Not Just Outcomes

One lesson reinforced repeatedly through Grandpa Days is the importance of praising effort rather than simply celebrating results.

When Serena was learning to read, we developed a simple routine. I read the left page of a book, and she read the right page. Gradually she took over more of the story until she was reading entire books aloud. Her confidence grew not because of natural talent but because effort was encouraged.

Great leaders build organizations the same way. Teams thrive when persistence, learning, and experimentation are valued as much as final results.

Resilient companies are built by resilient people.

Patience Is a Leadership Advantage

Modern business culture often rewards speed. Quarterly targets, rapid scaling, and constant urgency can create the illusion that everything must happen immediately. Grandchildren offer a powerful reminder that meaningful development takes time.

Confidence develops through repetition. Curiosity grows through exploration. Character emerges slowly through experience.

The same is true in business.

The strongest organizations are built patiently through shared values, trusted relationships, and long-term thinking. Patience in leadership is not the absence of ambition. It is the discipline to build something that lasts.

The Real Meaning of Legacy

At some point in every CEO’s career, a simple question emerges. What will remain after I am gone? Revenue milestones fade. Markets evolve. Even successful companies eventually change. What endures are the people we influence and the values we pass forward.

During one of our regular breakfast conversations, my grandson Felix looked across the table and said something I will never forget. “Grandpa, you are a big part of the man I’m becoming.” That moment meant more to me than any quarterly result or business milestone.

Over time I realized that whether you are mentoring a child or leading an organization, the principles are remarkably similar.

Show up.

Listen carefully.

Encourage curiosity.

Praise effort.

Practice patience.

These habits help children grow into confident adults. They also help leaders build strong, resilient companies. In both families and organizations, the mission is the same: helping the next generation develop the grit, smarts, and character they need to thrive.

The best leaders I know understand something simple. Leadership is not just about building companies. It is about building people.