If you’re a subscriber to this newsletter then you may have seen my recent articles discussing the topic of leadership and the evolution of my leadership style. You may have even heard me go in-depth on this subject in Episode 13 of the Clockwork CIO Podcast with James Williams. The feedback from that conversation in particular inspired a series of articles, where I’ve decided to share my personal philosophy on what effective leadership looks like in today’s world.
Over this series of 6 articles, I’ll dive into key aspects of leadership that I’ve found essential during my 35+ years in the field. These lessons 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.
With articles #1 and #2 already published on our site, this week we’ll explore how having a passion for lifelong learning and continuous improvement are critical qualities as a leader.
Lesson #3: Focus on Continuous Improvement
Leadership isn’t about knowing everything, nor is it about having all the answers upfront. It’s about being committed to constant learning, growing, and being intellectually curious. One of the most powerful lessons I’ve learned throughout my career is the importance of continuous improvement—a philosophy that I encourage and try to live by every day.
Continuous Improvement in Leadership
I was recently reading Relentless: From Good to Great to Unstoppable by Tim S. Grover. The book talks about how to cultivate an elite mindset and achieve extraordinary success in any field. The concept is simple, yet profound: no matter what obstacles we face, we all have the ability to grow and fulfill our potential. But as Grover explains, reaching the top requires relentless self-awareness and the discipline to improve continuously. He uses the term “Cleaners” to describe individuals like Michael Jordan and Kobe Bryant, those who never settle for just being good. They thrive under pressure, always striving to be better, no matter how successful they become.
David Senra’s Founders Podcast echoes this sentiment, noting: “The greats never stop learning. All the hours of work have created an unstoppable internal resource they can draw on in any situation.” I’ve found this to be true in my own life as well. Curiosity about the world and a desire for diverse perspectives are key to personal growth and self-improvement. And, no one becomes great on their own—leaders need strong teams that complement their strengths and push them further.
Orlando Gemes, Founding Partner & CIO of the credit-focused hedge fund Fourier Asset Management, who coincidentally was recently interviewed by James Williams on The Clockwork CIO podcast, once said:
“There have been a lot of times in finance where I’ve found that a wide range of opinions are not acceptable, that people don’t want to hear (them). Most people want the team to follow a single-minded approach. I think that’s a big part of the problem on the sell-side (investment banking). It’s also a big problem in asset management.”
When Michael Jordan played for the Chicago Bulls, his teammates had to rise to his own exceptional standards. While his talent was undeniable, his greatness was amplified by his coach, Phil Jackson, and teammates like Scottie Pippen and Dennis Rodman. Jordan was famous for practicing with the same intensity as he played in games, but it was the synergy between his leadership and the unique strengths of his teammates that led to success. Even Dean Smith, Jordan’s coach at the University of North Carolina, once remarked, “He was one of the most competitive [players] we’ve ever had in our drills. Like everyone else, he wanted to get better but then he had the ability to get better.”
Embrace Lifelong Learning & Feedback
The journey of leadership is not one with a clear endpoint—it’s a continuous process. Adopting the Japanese business philosophy of kaizen, or continuous self-improvement, is essential for anyone serious about building a successful organization. A good leader understands that they are always evolving. After every deal I’ve closed or project I’ve led, while I may feel proud of that accomplishment, I don’t let that moment linger. Success is fleeting, and the focus quickly shifts to what’s next.
Malcolm Gladwell famously talked about the “10,000-hour rule,” which highlights the importance of sustained practice to achieve mastery. True excellence doesn’t happen overnight. It’s about day-in and day-out progress, no matter how incremental. For leaders, the challenge is to push for improvement even when everything seems to be going well. It’s easy to make changes when things are falling apart, but it takes real leadership to initiate change when the business is thriving.
In my career, I’ve often taken on too much responsibility myself, willingly, thinking I could fix everything. But as I’ve gained experience, I’ve learned the value of seeking out other perspectives—especially from people who see the world differently than I do. Today’s culture, particularly on social media, often creates echo chambers that reinforce what we already believe. Real growth comes from listening to those who challenge our thinking.
A few months ago, I decided to hire a business coach—not because anything was fundamentally broken, but because I’m committed to always improving. One of the most important things I’ve learned is to pick a coach who doesn’t think like you. I’ve worked with coaches who echoed my thoughts and told me what I wanted to hear. That might feel good, but it doesn’t push you to grow. Real feedback comes from someone who can point out your blind spots.
At my former company, where I spent three decades of my career, I never once received a formal performance review. Yes – not once. Every year, I’d ask my leader for feedback —“Tell me three things I could do differently or better”—but I never received it. Instead, the conversation always shifted to stock options or pay raises. While those were certainly appreciated, they didn’t help me improve. They didn’t help me grow. Feedback is essential, whether it’s in sports, business or relationships. It’s what helps us refine our craft and get better at what we do.
In business and sports – or any other competitive field – we learn more from the moments where we fall short than from our victories. When I played baseball, I never dwelled on my batting average or the number of home runs I hit – I focused on the pitches I missed, the strike outs I made or balls I hit into an out. Why did I miss? Was it my stance? Did I not see the pitch correctly? Was I distracted? Similarly, in business, we need feedback to grow. Leaders have a responsibility to provide – and receive – that feedback, both positive and negative. When done with honesty and empathy, it helps people grow. When it’s absent, people can stagnate, losing confidence and direction.
How one conveys feedback effectively is just another aspect of kaizen in the business world.
Mike Steed, Founder & Managing Partner of Paladin Capital once said something I totally agree with:
“Hire the best people. Guide them. Empower them. Let them do their job. You cannot be intimidated by smart people.”
Similarly, General George S. Patton also once said
“Don’t tell people how to do things; tell them what to do and let them surprise you with their results.”
They’re both absolutely right, and I couldn’t agree more. In a company where the culture is built on fear or blind authority, you won’t get innovation or loyalty. But while doing so, it’s vital to also communicate negative information, as well as provide accolades, in a fair and honest way – be truthfully yet empathetically transparent – so that employees know both where their strengths lie and what they need to work on.
At PPR, after a recent independent board of directors meeting, I asked for feedback. Initially, the response was, “Everything’s great.” But I pushed for more, and finally, it was suggested that we distribute meeting materials earlier. It wasn’t a huge change, but it was valuable. It also helped me realize that it made sense for someone else to manage that task, and we are putting a better process in place. People often say to only focus on the big things, but I know that there are many more of these small fixes out there, and over time if we do many of these, the company will grow, be more efficient, and succeed faster over the long term. Small improvements, when consistently applied, can have a big effect for me and our firm over time. Small things do matter.
Self-Directed Learning
I’ve always believed in the importance of self-directed learning. I’m an upfront kind of guy. I’ve no problem letting people in the firm know, ‘Hey, I’m still learning, I’m still reaching out to my network. I need different perspectives. I challenge anyone to say a desire to continually improve is a negative attribute. In fact, being resourceful and intellectually curious is one of PPR’s core values.
At PPR, we’ve set aside a budget for every employee to pursue educational opportunities outside of the internal training we provide. It’s up to each person to decide how they want to use that budget, whether it’s attending a seminar or taking a course, because personal growth benefits not just the individual but the entire company.
CEOs have a unique opportunity to self-improve by surrounding themselves with knowledgeable, capable people. I firmly believe in and adhere to the mindset of: You don’t hire talented people to tell them what to do, you hire them to show you what they can do. That’s what makes companies thrive over the long-term. As kaizen teaches us, transformational change happens one small step at a time. We’re all grains of sand, but with the right approach, everyone can become a pearl.
Stay tuned for upcoming articles in the coming weeks where we’ll delve into other topics including:
• Transparency
• Failing fast
• Daring to dream
