Leadership is often defined as an ability to effectively guide and motivate others, usually in an organization, in order to achieve goals. In a growing company, like PPR, it’s imperative to not only personify leadership for your followers but also to explain the value of it to others. In a recent series of articles, I’ve discussed the power of open dialogue, persistence, and authenticity, as well as the importance of making continuous improvement. These were all topics you may have even heard me go in-depth on with a podcast from earlier this year, called the Clockwork CIO Podcast with James Williams (Episode 13).
It was the feedback from that conversation that inspired this series of articles, where I’ve decided to share my personal philosophy on what effective leadership looks like in today’s world. Throughout this series I’ve been diving into key aspects of leadership that I’ve found essential during the 35+ years in my career. These are lessons that come from both successes and mistakes, with the aim of helping you grow as a leader and make your teams stronger, more productive, and ultimately more successful.
For this week’s piece on the subject, I wanted to talk about the concept of failure and why it’s not only what we endure that can be learned from but the speed in which failure can allow us to successfully continue forward.
Lesson #5 – Fail Fast, Learn, and Keep Moving Forward
One truth I’ve learned over the years is that every leader has faced significant challenges. Think of John Pierpont Morgan, who established one of the most powerful banks in history. In 1901, he founded Northern Securities Company, only to be sued by President Roosevelt’s government under the Sherman Antitrust Act the following year. That was the first major antitrust case, and it effectively ended Morgan’s plans for industrial consolidation. Then, in 1902, he failed again—this time when his bid to build a subway line in London was blocked by a transit magnate, crazily enough from Philadelphia. These weren’t small missteps.
But those setbacks didn’t stop Morgan. By 1907, during a financial crisis that could have crippled the U.S. economy, he played a pivotal role in saving it. Failure didn’t define him—it taught him. JPMorgan Chase is now the 5th largest bank in the world.
The lesson here is clear: It’s okay to fail – in fact it’s imperative you do – provided you do so quickly and learn from it.
My own son recently faced a challenge. He’s in real estate, and after moving from Pennsylvania to New Jersey, he had to take a new realtor exam. New Jersey’s test is notoriously difficult, and he failed it twice. That second failure hit him hard. But rather than let it defeat him, I reminded him that failure is often just a signal that something in the approach isn’t working. I asked him, “What’s your new strategy for next time? What will you change to get it right?” And the third time, he passed.
I like Henry Ford’s quote:
“Failure is simply the opportunity to begin again, this time more intelligently.”
Here at PPR, I’ve heard a few people say, “Well, we failed at this.” My response is always the same: “No, we didn’t fail. We found a way that didn’t work, and now we know what to avoid next time.” The sentiment is important, but words matter. And when you deliver them with conviction, people start to believe them. It’s about reinforcing the right culture—a culture that values learning from failure rather than fearing it.
Now, I’m not saying failure is something to celebrate. It hurts. It can be demoralizing. But sometimes, failure is necessary because it shows us we’re pushing boundaries. As long as the missteps don’t cause irreparable damage, people shouldn’t have to fear that trying something new will land them in trouble.
The key, though, is to fail fast, learn from it, and keep moving forward.
This attribute or sentiment can come from anyone, anywhere. Jordan Jonas, who won the role in TV series “Alone,” said in an interview that:
“Being able to handle failure—and the sooner you can, the better—is a muscle you have to exercise.”
Look at Michael Phelps, the greatest swimmer of all time. People admire his gold medals, but they rarely see his struggles with ADHD, the countless races he lost, the pain, the early mornings. Or Richard Branson, who has been candid about his struggles with dyslexia. He didn’t let it hold him back; he found a way through.
Phil Knight, who founded Nike, is another great example. He started by selling shoes out of his car and made $8,000 in his first year. Today, Nike’s annual revenue is over $50 billion. That didn’t happen in a straight line. Knight faced fierce competition and legal battles but he persisted.
I’m a huge reader of history and love reading when Winston Churchill famously said:
“Success is going from failure to failure without losing enthusiasm.”
By sharing our failures and demonstrating what we’ve learned from them, we build a stronger corporate culture. If you don’t believe in the direction you’re heading, no one will follow you. And that’s when failure becomes fatal.
Legendary basketball coach Dean Smith used the acronym RALF to help his players deal with mistakes: Recognize it, Admit it, Learn from it, and Forget it. It’s a smart approach, especially in sports where micro-moments matter. However, I would add that while we shouldn’t dwell on our failures, we should keep them in the back of our minds as a tool for future challenges. When you face a familiar problem, you can say, ‘I’ve been here before, and I know what I learned.’
To reiterate, here’s what Bill Gates once said:
“It’s fine to celebrate success, but it’s more important to heed the lessons of failure.”
Failure is pattern recognition. The more you experience, the better you become at identifying what works and what doesn’t. It’s what makes artificial intelligence so powerful—every failure informs the next decision.
Personally, I’ve always been a passionate person (yes, I’m also Italian so there’s that). Early in my career, I struggled more with failure. I’d get loud, and that made people uncomfortable. And at six-foot-five and weighing in at 270 pounds, that’s a powerful presence. But as a leader, you can’t let stress trickle down to your team. And over time, I learned that as the CEO, you have to be the calm in the storm. When you raise your voice, people pick up on it, and it can cause unnecessary panic.
One of the toughest moments in leadership is realizing you still believe in something but know you need a new approach. This is exactly what I taught my son. It’s easy to stick with something too long, hoping it will work out, but hope isn’t a strategy.
Last season, the offensive coordinator for the Philadelphia Eagles refused to change his strategy, even when it clearly wasn’t working. The fans were booing, and yet he stayed the course. They lost seven of their last eight games. It takes courage to admit you’re wrong and to pivot. But it’s often necessary for the success of the team—and for yourself.
Celebrating success if important. It’s a testament to good decisions and a well-executed plan. But I’ve learned that while it’s important to celebrate success, people respond more positively when you acknowledge failure, take the hit, and find a new way forward. Success feels great, but recognizing failure—and quickly—can lead to even greater achievements.
In leadership, it’s not about never failing; it’s about how fast you can acknowledge mistakes, pick yourself up and move on. That encourages even more success.
So, what is the takeaway from this? As leaders, we need to embrace the reality and “burn” of failure. If you “trust the process,” failures are a necessary part of “the process”. We need to see failures for what they are, not the end, but the beginning of a new way forward. We need to let the lessons from failures shape our perspective and course going forward, not let them derail our progress. As leaders, if we can do this and build a culture that accepts and rallies around this, then we’re all on the path forward!
