5 Leadership Lessons from Back-to-School Advice

This August, What If We Took Our Own Advice? 5 Leadership Gems to Remember at Work

Every August, parents send their kids back to school armed with the same timeless advice: be curious, make new friends, ask for help when you need it, treat everyone kindly, and remember that mistakes are how you learn. We say it with conviction. We mean every word.

When he was younger, I used to tell my son at school dropoff each morning, "Be a good leader. Make good decisions and ask good questions. Ask for help if you need it.” At night, I tell him, "Be confident but humble and help people and animals who need your help.”

So much great wisdom we share. And then we walk into our own offices and do none of it.

The irony is hard to ignore. The wisdom we confidently hand our children, the stuff we know in our bones to be true, evaporates the moment we sit down at our desks and feel the weight of titles, deadlines, and quarterly targets.

Be Curious: Ask Questions, Even When You Think You Should Know the Answer

We tell kids: there are no stupid questions. Raise your hand. Wonder out loud.

We tell ourselves: project confidence. Don't show uncertainty. Have the answer before the meeting starts.

Yet the research is unambiguous. According to Forbes, while 96% of executives claim they embody a growth mindset, only 45% of employees agree that their leadership actually demonstrates it in practice. Classic case of do as I say, not as I do.

The leaders who navigate uncertainty best are the ones who don't pretend to know all the answers. Show me a leader who says they have it all figured out and I'll show you a leader who is irrelevant. The ones who remain genuinely curious about the questions are the ones who get results and pull in other perspectives to make a better decision. To paraphrase my Both/And leadership philosophy, curiosity and conviction are not mutually exclusive.

Make New Friends: Build Relationships Before You Need Them

We tell kids: introduce yourself. Sit with someone new. You never know who might become your next best friend.

We tell ourselves: I don't have time for relationship-building right now. I'll connect after the project is done.

But connection is not the reward for getting work done. It is what makes the work possible. Psychological safety, the foundation of every high-performing team, is built in the small moments of genuine human contact, not in all-hands meetings. Leaders who invest in relationships before a crisis hits are the ones with teams that hold together during one.

It Is Okay to Not Know Everything: Ask for Help

From a young age, we are taught a simple lesson: when you are confused, raise your hand. The teacher is there to guide you, ensuring you do not have to solve problems on your own. This principle is foundational to how we encourage children to learn and grow.

Yet, as adults, we often adopt a completely different mindset. We tell ourselves that asking for help signals weakness, that we should have the answers figured out on our own. This shift in perspective can be detrimental, especially for those in leadership positions.

Just as teachers meet students where they are, effective leaders recognize that learning never truly ends. They understand that leaning on others to accomplish shared goals is not a sign of vulnerability but a demonstration of strength. By admitting what you do not know and seeking support, you model a growth mindset for your entire team, fostering an environment where curiosity is valued over pretense.

Treat Everyone With Kindness…Even People Who Are Different From You

Children are taught to include those who are left out, to be kind to the new student, and to appreciate that differences make things interesting. These are fundamental lessons in empathy and inclusion.

As we mature, we often claim to value diversity, yet our actions may not align with that belief. It is easy to fall into the trap of hiring and promoting people who reflect our own image, inadvertently creating homogeneous teams. This is where empathy must become a practice, not just a value statement on a website.

Leaders who build the most innovative and resilient teams are those who actively seek out differences in background, perspective, communication style, and experience. This approach has tangible benefits. Michele Feferman, founder of Equity at Work, discussed on The Empathy Edge podcast how investing in diversity and creating a culture of belonging can lead to higher profits, better margins, and improved retention. Furthermore, research from Catalyst supports this notion, revealing that 61% of employees with empathic leaders report being able to innovate, compared to just 13% of those with less empathic leaders. Empathy is not just a soft skill; it is a driver of business success.

Mistakes Are How You Learn: Treat Failures as Data, Not Personal Flaws

We reassure children that it is okay to get things wrong; that is part of the process of figuring things out and trying again. Mistakes are framed as learning opportunities, not character defects.

In the professional world, however, the narrative often shifts to "failure is not an option." Especially during times of uncertainty, we may feel we cannot afford to make mistakes. Yet, in an era of constant change and AI disruption, organizations that punish failure are essentially punishing learning—the only real competitive advantage remaining.

Amy Edmondson, in her book Right Kind of Wrong: The Science of Failing Well, explains that the highest-performing teams are not those with the fewest mistakes. Instead, they are the ones that talk about mistakes openly, learn from them quickly, and cultivate a climate of psychological safety. By treating failures as data points rather than personal flaws, you create a culture where calculated risk-taking and innovation can thrive.

Leaders: Take Your Own Advice

As the summer winds down and the Q4 sprint approaches, consider trying something radical: take the advice you gave your child—or that you received—on the first day of school. Get curious about a new topic. Build a new connection with a colleague. Admit what you don’t know without shame. Include someone who has been left out of the conversation. And when something goes sideways, treat it as a lesson rather than a verdict.

The wisdom we impart to children was right the first time. We simply forgot that it applies to us too, and it is never too late to start practicing it.