The One Decision That Changed Everything: Peter J. de Silva of IRALOGIX On How a Single Choice Can Redefine A Leadership Journey

An Interview With Jim Hamel

Leadership isn’t about projecting strength all the time. It’s about being real, being steady, and creating an environment where people can do their best work. It’s about trust.

Asa part of this series, we had the pleasure to interview Peter J. de Silva.

Peter de Silva, author of best-selling Taking Stock:10 Life and Leadership Principles from My Seat at the Table (Gravitas Press, 2023), is a Harvard senior fellow in the acclaimed Advanced Leadership Initiative. An experienced chairman, CEO, and board director, he has held leadership roles in public and private companies and nonprofit organizations. He currently serves as CEO of IRALOGIX, the retirement industry’s leading fintech pioneer.

Thank you so much for joining us in this interview series! Can you share the most interesting story that happened to you since you started your career?

After an almost 40-year career there are a lot of impactful moments I could point to, but one really stands out, which I wrote about in my book.

Early in my career at Fidelity Investments, my boss walked in one day and said, “Your desk is moving to Northern Kentucky, and you need to go with it.” After some reflection, I pushed back. I said no. He said yes. We went back and forth, and I held my ground.

About a month later, he sat me down again and said, “You’re not hearing me. This isn’t optional. This is important for your career development.” He wasn’t being harsh. He genuinely believed it would help me grow. He wanted me out of the home office, in my own environment, with the chance to take real ownership, exhibit real leadership, operate with more autonomy and less bureaucracy.

At the time, I was in my early 30s and already one of the youngest senior vice presidents in the company. This was a defining moment. It wasn’t discipline. It was mentorship.

So I went. I moved to Covington, Kentucky, and took on what was a very difficult situation. The operation was struggling. It was a greenfield site with no real cultural connection back to Boston headquarters. Local leadership had largely been recruited from other financial services firms. They were very capable, but they didn’t fully understand Fidelity or the Fidelity culture, and there was a disconnect in how teams worked together. A big part of my job was to build those bridges and make the place feel like Fidelity, even though it was hundreds of miles away.

Then something strange started happening. My boss would show up almost every week. He’d fly in, go straight to his office, close the door, handle his meetings, and leave. We’d exchange a quick hello, maybe grab dinner occasionally, but that was it. This went on for about a year, and I never really understood why. It wasn’t until after I finished the role and was asked to move back to Boston for a promotion that it all clicked.

What I didn’t fully appreciate at the time was that the Fidelity corporate executive team had some concerns. I was young, a bit unpolished, and they were asking me to fix a high-visibility problem. It was on Ned Johnson’s radar. It mattered.

Fred’s weekly visits were intentional. First, he was there in case I needed support. This was before Zoom or Teams, so being physically present mattered. Second, he was signaling to senior leadership: “I’ve got this. I’ve got Peter’s back.”

The key is, he didn’t interfere. He trusted me to do the job. He gave me space, but he made sure I wasn’t exposed.

After I put it all together, I went into his office and asked him directly, “What were you doing all that time?” He brushed it off at first, but eventually he said, “I was there if you needed me. And I was there, so everyone else knew you were supported. But you didn’t need me.”

That experience stuck with me. What he did was stretch me further than I thought I could go, but he also built a safety net around me. He wasn’t going to let me fail.

That was one of the most formative experiences of my early career.

That’s something I’ve carried with me ever since. I think about it as building guardrails around people, especially up and coming leaders. You give them room to move, to make decisions, to take ownership. You let them roam. But you’re watching. You’re monitoring. And when needed, you step in and ask probing questions. Sometimes you let them proceed. Sometimes you help them adjust.

But the goal is the same. Push people to grow, while making sure they’re supported.

What do you think makes your company stand out? Can you share a story?

We’re client-partner obsessed. That’s really the simplest way to say it.

We’re very clear on why we exist and who we serve. We’re a B2B2C organization, and everything we do is focused on helping our partners succeed. That shows up in a lot of ways. We help them retain clients, grow relationships, reduce operational friction, and ultimately drive more revenue and better outcomes. If they win, we win. It’s that straightforward. It’s a mutually beneficial arrangement.

What makes us different is how seriously we take that. It’s not just a talking point. It’s not just words on a coffee cup or a shirt, it’s how we operate every day.

A big part of that is the platform itself. At IRALOGIX, we built our technology from scratch. It was built specifically for IRAs. It wasn’t retrofitted. It wasn’t adapted from something else. It was purpose-built for this space, and that matters because it lets our partners deliver a much better experience to their clients.

You can see the impact in the way our partners talk about us.

We have one partner who joked that he’d get an IRALOGIX tattoo if we let him. What he meant was that he’s out there every day selling our value proposition. Not just the technology, but the whole package. Better client experience, smarter operations, aligned economics. For him, it’s easy to stand behind because it works.

Another example is a large, national insurance company. I had dinner with their team recently, and they kept coming back to two things. First, how aligned we are strategically. Second, how much we’ve helped them grow.

They told me their IRA business, powered by our platform, is now the highest margin, most profitable segment in their company. That’s a big statement. But what really stood out is how it’s changed the way they show up in the market.

Everything is white-labeled, so it looks and feels like the partner themselves. But behind the scenes, it’s a completely modern platform. Their advisors now have better tools, better investment options, and a smoother experience overall. And that flows all the way through to their end clients.

One more quick story. A few years back our President. Pete Littlejohn, walked into a prospect and made our pitch. Before the meeting was even over, their CEO asked for the contracts. His reaction was simple: what we were offering didn’t look like anything else in the market. That partnership has since grown into one of our largest.

So when I say we’re partner-obsessed, that’s what I mean. We build things that genuinely help our partners grow, and we stay close enough to make sure they actually do.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

I’d point to three traits, in no particular order: humility, a sense of purpose, and integrity.

First is humility. Whatever success I’ve had hasn’t been mine alone. It’s come from the people around me. Teams that helped build companies, support clients, and execute on big ideas. I’ve always believed that, and I think people respond to it. They can tell when a leader gives credit versus when they take it.

I actually learned that lesson the hard way early in my career at Fidelity Investments. I worked on a complex tax issue that ended up saving the company a few million dollars. My boss was thrilled and gave me a $10,000 bonus.

I took it, deposited it, and spent it. But later, it didn’t sit right with me. I hadn’t done that work alone. There were people behind the scenes doing the heavy lifting, and they didn’t get anything. That stuck with me.

I can’t go back and change that moment, but it shaped how I lead now. I make a point to share credit, recognize people publicly, and make sure the rewards, financial or otherwise, are more evenly distributed. That’s what humility looks like in practice.

Second is a sense of purpose. You can tell people what to do because you’re the boss. Or you can give them a reason to care. I’ve always believed purpose matters more than strategy. Strategy is important, of course, but purpose is what actually motivates people. It’s what gets them out of bed in the morning.

At IRALOGIX, we talk a lot about transforming the way Americans save for retirement. That’s the bigger picture. That’s what makes the day-to-day work meaningful, even when parts of the job are routine or difficult.

And it’s not just about my own sense of purpose. It’s about helping every person on the team understand how their role connects to that mission. When people see that connection, their work changes. It becomes more personal, more intentional. I’m fond of using the phrase, “One Dream, One Team.” Those are not just words, it’s how we function.

Third is integrity. It sounds simple, maybe even cliché, but it’s everything when things get difficult.

At the end of the day, you have to be able to look at your decisions and know you did the right thing. Not just what was easy or convenient, but what was right.

For me, that shows up most clearly when something goes wrong. And things do go wrong. When they do, we take responsibility. We fix the problem. And if it costs us, it costs us. That’s part of doing business the right way.

I’ve always believed integrity is what you do when no one’s watching. I’m not perfect, but I’ve tried to lead that way and build organizations that operate that way too.

When you put those three together, humility, purpose, and integrity, they reinforce each other. They shape how you lead, how you build teams, and how people experience working with you.

What was the pivotal decision that transformed your approach to leadership, and what prompted you to make it?

That one is pretty clear for me.

The pivotal shift in how I lead came when I decided to be open about a rare disease I’ve lived with my entire life, called Charcot-Marie-Tooth disease, or CMT.

For most of my career, I kept it private. I didn’t want people to see me differently or think I was somehow less capable. So I pushed through it quietly and kept that part of my life to myself.

That changed about ten years ago when I was at TD Ameritrade. I was going through a difficult stretch and finally opened up to my boss at the time. I remember being hesitant. I expected it might change how he saw me.

Well, I was partially right. It did change the way he looked at me, but it had the opposite effect than I was expecting.

He respected it. He saw it as a sign of resilience and determination. That moment really stuck with me. It forced me to rethink something I had carried for years. Not long after, I made a conscious decision. I wasn’t going to hide it anymore. I was going to be open about it.

That decision was incredibly liberating. It shifted my mindset from worrying about how I might be perceived to focusing on how I could connect with and help others. I often say CMT isn’t who I am, it’s just something I have. Once I accepted that, everything changed.

It also reshaped how I lead.

Living with CMT since childhood has given me a deeper sense of empathy. There are a lot of people dealing with challenges you can’t see, physical, emotional, or otherwise. When you’ve lived that yourself, you tend to lead with more patience, care, and understanding.

That doesn’t mean lowering standards. I still expect a lot. But I try to meet people where they are and recognize that everyone is carrying something.

It also reinforced something else in me. I’ve always felt I had to work harder to keep up. I’m not the smartest person in the room, and I’m fine saying that. But I will outwork just about anyone. That mindset has been shaped, in part, by what I’ve had to overcome.

So if I had to point to one pivotal decision, it was choosing to be open. That shift didn’t just change how people saw me. It changed how I saw myself, and ultimately, how I lead others.

How did this single choice impact your personal growth and your view on what it means to lead?

The decision to be open about living with Charcot-Marie-Tooth disease had a profound impact on my personal growth and how I think about leadership.

Before that shift, I carried a lot of internal pressure. I felt like I had to prove myself constantly. That showed up at times in how I led, especially in high-stakes moments.

I remember stepping into a major leadership role at TD Ameritrade. There was a lot of scrutiny. I was replacing a long-tenured executive, the entire industry was watching. There were hard questions in the market about who I was and whether I was the right choice.

I felt that pressure. And for a period, it pushed me slightly off center. I became more directive than I should have been. I listened less. I was focused on proving I deserved the role instead of leading the way that had gotten me there in the first place.

Around that time, I started working with an executive coach who helped me see that clearly. He challenged me in a simple but important way. He said, “Why are you trying to be someone else? The reason you’re here is because of who you are, and how you lead, not despite it.”

That was a turning point.

And it connected directly to my decision to be more open about CMT. Because once I stopped hiding that part of my life, I stopped feeling like I had to compensate for it.

That changed how I showed up. I became more grounded. More consistent. I leaned back into the leadership style that had always worked for me, one built on relationships, humility, and listening.

It further deepened my empathy. When you’ve had to work through something personal for most of your life, and then you choose to be open about it, you start to see others differently. You realize how many people are dealing with challenges you can’t see.

That shifted my view of leadership in a meaningful way.

Leadership isn’t about projecting strength all the time. It’s about being real, being steady, and creating an environment where people can do their best work. It’s about trust.

Over time, that approach paid off. It took about a year to really earn the trust of the organization, but once I did, the culture strengthened, relationships improved, and the team performed at a higher level.

So if I look at the impact of that decision, it did two things.

Personally, it gave me a level of confidence and freedom I didn’t have before. And as a leader, it brought me back to my North Star. It reminded me that the best way to lead isn’t to change who you are under pressure, but to double down on what makes you effective in the first place.

What were some of the immediate and long-term effects of this decision on your team or organization?

It’s hard to point to a single, immediate effect, because this wasn’t just one decision. It was a series of experiences that shaped how I lead over time.

I think of it as a mosaic. Every person I’ve worked with, every challenge, every move, they all become part of how I see the world and how I lead. Those pieces don’t go away. They stay with you.

That said, when I became more open about living with Charcot-Marie-Tooth disease, and more intentional about leading with empathy, there were some clear shifts.

In the short term, it changed how I connected with people. I became more approachable. Conversations got more real. People were more willing to share what they were dealing with, not just at work, but in life. That creates trust, and trust changes how teams operate.

Over the long term, it shaped the kind of culture I’ve tried to build.

I’ve become deeply focused on the experience people have inside the organization, not just the experience we deliver to clients.

At IRALOGIX, I spend a lot of time thinking about that. There’s a simple belief behind it: if you take care of your people, they’ll take care of your clients, and the rest takes care of itself.

That shows up in small, consistent actions. I make a point to recognize extra effort. I invest time in relationships, both with employees and our client-partners. I still write handwritten notes for employee anniversaries and send them to their homes, because I want that moment to feel personal, something they can share with their family. It’s a small thing, but it matters. Over time, those actions add up. You start to see higher engagement, stronger relationships, and a culture where people feel valued, not just for what they do, but for who they are.

All of this traces back to the same realization. People are at the center of everything. That sounds simple, but actually living it takes effort and consistency.

For me, that’s been the lasting impact. A deeper focus on people, a stronger commitment to relationships, and a leadership style grounded in understanding that if you get that part right, a lot of other things fall into place.

How did you handle uncertainty or doubt while making this critical choice?

I’ve dealt with a lot of self-doubt over the course of my career. Anyone who tells you they haven’t is probably not being honest.

There’s always an external side of leadership where you project confidence and direction. But internally, there are moments when you question your decisions, especially when you’re dealing with complex situations where results take time to show up. What’s changed for me is how I handle that doubt.

First, I don’t ignore it. I check it. When I make a decision, I come back to it and ask, “ Is this actually producing the outcome we expected?” Sometimes the answer is yes. Sometimes it’s no. And when it’s no, I’m willing to adjust. I’m not so locked into a decision that I can’t change course. If new information comes in or something isn’t working, we shift. That’s not weakness. That’s good leadership.

Second, I rely on effort and discipline. When I’m uncertain, I lean in. I work harder. I stay close to the details. I spend more time with the team. Action helps create clarity.

A good example of this was when I left Fidelity Investments and took on the role of president at UMB Financial Corporation.

To be candid, I was in over my head at first. I didn’t come from a traditional banking background. I didn’t have deep experience in areas like commercial lending or asset-liability management. And I knew it.

I remember telling the bank’s chair during the interview process, “If you want a traditional banker, I’m not your guy. If you want a leader, I might be.” I also told him I was concerned the organization would reject me. There were a lot of classically trained bankers there, and I was coming in from a different world.

He didn’t sugarcoat it. He said, “You’re right, some of them won’t accept you right away. You will need to win them over. I’m confident your leadership skills will trump any gaps in your banking knowledge. Be patient. Learn from them. I’ve got your back.”

That mattered.

Even with that support, the doubt didn’t disappear. It probably took me a year to really earn the trust of the team.

And I didn’t do it by forcing direction or trying to prove I was right. I did it by listening. I asked people what they needed to be successful. What would help them win more business. What would make their jobs easier.

That approach changed everything. It shifted the dynamic from “follow me” to “I’m here to help you succeed.” That’s when things started to click.

So for me, handling uncertainty comes down to a few things. Stay honest about the doubt. Keep evaluating your decisions. Be willing to adjust. And most importantly, stay close to your people.

Because in the end, real success doesn’t come from pretending you have all the answers. It comes from being willing to figure them out.

What lessons did you learn from this decision that you continue to apply in your leadership today?

That decision taught me a set of lessons that I still carry with me every day. In many ways, it reshaped how I think about leadership at a fundamental level.

Confidence has to be earned, and it has to be grounded. There’s a very real line between confidence and arrogance. I’ve always tried to stay well on the right side of that line. People want to follow leaders who are clear, decisive, and confident in their direction. But at the same time, they’re quick to disengage if that confidence turns into arrogance.

For me, being open about living with Charcot-Marie-Tooth disease helped anchor that balance. It forced me to be honest about who I am, strengths and limitations included. Once I stopped feeling like I had to prove something or compensate for something, my confidence became more natural. It wasn’t performative. It was earned.

Leadership starts with listening, not talking. There is an old saying that God gave humans two ears and one mouth so they could overemphasize the listening part. Earlier in my career, especially in high-pressure situations, I probably leaned too far into directing and deciding. But over time, and especially after making the decision to be more open, I realized that the best outcomes come from truly understanding what’s happening around you.

Today, I spend a lot of time listening. I make it a point to connect with people at all levels of the organization, not just those in the executive circle. Those conversations are invaluable. They not only make me a better leader, they allow people to feel heard. And when people feel heard, they’re more engaged, more invested, and more willing to contribute.

Leadership is service, not status. This is probably the biggest shift. At some point, you realize leadership isn’t about being in charge. It’s about being responsible for others. Your job is to create the conditions for people to succeed. That means removing obstacles, providing clarity, making tough calls when needed, but also supporting people in very real, human ways.

Consistency matters more than intensity. Anyone can show up strong in a moment. What matters is how you show up over time. For me, that means reinforcing these principles every day. Listening. Giving credit. Being present. Staying grounded. Making sure people know they matter. That’s how trust is built.

How has this decision influenced the advice or guidance you offer to emerging leaders?

The decision to be more open, more self-aware, and more grounded in how I lead has definitely shaped the advice I give to younger leaders. A few things come up again and again.

First, focus on the job you have, not the one you want. I tell people this all the time. Don’t get too caught up in chasing the next role. Do excellent work where you are, and the next opportunity will show up. Careers aren’t as linear as people think. If you stay focused on doing great work and putting in the effort, you’ll get noticed. The path tends to reveal itself over time.

Second, find mentors early. This is a big one. You need people who can give you an honest, objective perspective. And in most cases, that shouldn’t be your boss. A good mentor helps you see around corners. They challenge your thinking, help you process decisions, and keep you grounded.

Third, decide what kind of career you want. At some point, you’ll need to choose whether you want to go deep in a specific craft or broad into leadership. Both paths are valid. You don’t have to manage people to be successful. But if you want to lead, that’s a different skill set. It’s not just about what you know. It’s about how you work with others.

Fourth, emotional intelligence matters more than you think. I’ve seen incredibly smart people struggle because they couldn’t connect with others. And I’ve seen people with more average technical skills thrive because they understood how to lead, communicate, and build trust. Your raw intelligence will get you in the door. Your emotional intelligence is what determines how far you go.

Please share a story (or stories) that provide “color” around making this critical decision.

For me, that decision didn’t come out of nowhere. It was built over time through a series of experiences that, in hindsight, were all pointing me in the same direction.

One of the earliest influences was my upbringing. My parents were very grounded in values. They emphasized character, integrity, and doing the right thing, even when it’s hard or when no one’s paying attention. Those weren’t abstract ideas in our house. They were lived every day.

At the same time, I was growing up with Charcot-Marie-Tooth disease, and that created a different kind of challenge. I couldn’t do a lot of the things other kids could do physically. That was frustrating, and like a lot of kids, I didn’t want to stand out because of it.

My instinct was to keep that part of myself quiet. To push through it privately and not draw attention to it. But my parents took a different approach. They didn’t ignore it, and they didn’t let me ignore it either. They helped me face it directly and figure out where I could build confidence. For me, that was swimming and cycling. It gave me a few things to lean into instead of something to hide from.

Fast forward into my career, and I was still carrying that instinct to keep things private. Even as I moved into bigger leadership roles, I didn’t talk about CMT. What started to change wasn’t one dramatic moment, but a realization that came from watching and learning from others over time. I began to see that the leaders people trusted most weren’t the ones who projected perfection. They were the ones who were consistent, authentic, and real. They didn’t pretend to have everything figured out. They were comfortable being themselves.

Eventually, I made a conscious decision. I wasn’t going to keep that part of my life separate anymore. I was going to be open about it. Not for effect, and not to make a statement, but because it was the more honest way to lead. Once I made it, it felt like things clicked into place.

Were there any unexpected challenges or rewards that emerged from this choice?

Yes, there were both, and some of them were not what I expected.

On the challenge side, the biggest hurdle was internal. Even after I decided to be open about living with Charcot-Marie-Tooth disease, it didn’t immediately feel natural. When you’ve spent most of your life managing something privately, there’s a real adjustment that comes with bringing it into the open. There’s vulnerability in that. In a leadership role, that can feel risky. You start to wonder, “Will this change how people see me? Will they question my ability?”

But what I found pretty quickly is that the bigger risk would have been continuing to keep it hidden, because the rewards were significant. The first was connection. Almost immediately, the quality of my interactions with people changed. Conversations became more real. People felt more comfortable being themselves, and that creates a different kind of environment.

I also noticed that people started sharing more of their own experiences. It reinforced something I’ve come to believe very strongly. Everyone is carrying something. You just don’t always see it. And when a leader is willing to be open, it permits others to do the same.

There was also a personal benefit that I didn’t fully appreciate going in. For a long time, I carried this sense that I had to prove myself. Letting go of that was freeing. It allowed me to focus less on perception and more on impact. I became more consistent in how I led. More patient. More aligned with my own values. And over time, that shows up in the organization through stronger relationships and higher levels of trust.

If you could start a movement that would bring the most amount of good to the most people, what would that be?

If I could start a movement, it would be focused on helping young people build self-confidence and character.

That’s something I had to work through myself. Growing up with Charcot-Marie-Tooth disease, my confidence took some hits early on. I couldn’t run like other kids. Sports were tough. That stays with you. Over time, I found my way through it. Swimming became an outlet for me. It was something I could do, something I could improve at. And that started to rebuild my confidence.

That’s why this matters so much to me. If I were to build something, it wouldn’t just be about teaching skills. It would be about helping young people see what they’re capable of, especially the ones who feel overlooked or different. Because confidence and character carry forward. They shape how you approach challenges, how you show up in relationships, and what you believe is possible for yourself. You can teach someone how to do a specific task, but if you help them believe in themselves, you change the trajectory of their life.

How can our readers further follow your work online?

You can learn more about what we’re building at IRALOGIX by visiting www.iralogix.com.

If you want to dive deeper into my background and the leadership lessons I share in my book, you can find that at www.peterjdesilva.com.

And if you’d like to know more about Charcot-Marie-Tooth disease and the work of the CMT Research Foundation, you can visit www.cmtrf.org.

Thank you for sharing these insights!