Chief Change Officer
#195 Steve Monaghan: From Flying High to Finance Disruptor — No Seatbelts Required
Sun, 23 Feb 2025
Steve Monaghan went from piloting airplanes to piloting billion-dollar banking transformations—because why settle for one high-stakes job when you can have two? After trading in his wings for Wall Street, he’s spent 30 years disrupting finance and tech across Australia, Tokyo, and the Middle East. Now, with leadership roles at RAKBANK, FinMir.ai, and beyond, he’s proving that the real flight plan for success is innovation.Key Highlights of Our Interview:The Foreigner’s Lens“Being an outsider brings a unique perspective—an untainted view of industries and cultures. It’s about seeing things differently, learning from fresh angles, and questioning the norms others might take for granted.”“Being an outsider has its perks and pitfalls. It offers clarity but also means navigating unfamiliar landscapes. The key is turning the so-called disadvantage of not ‘belonging’ into a powerful tool for change.”Immigrant Wisdom - The Dual Edge“Living as an immigrant since my twenties taught me resilience and adaptability. You’re always learning, always adjusting, and that shapes how you approach leadership and problem-solving.”From Fear to Understanding“People don’t resist change because they don’t want it. They resist because they don’t understand it. The journey is about removing fear by turning a ‘no’ into a ‘know’—helping them see the benefits and feel confident about the new direction.”The Advantage of Experience - Ask the Right Questions“In the generative AI era, older employees often have an edge—they know how to ask better questions. This ability to craft meaningful queries is a huge advantage, especially when navigating tools that rely on prompt engineering.”“While younger employees might excel in technical adaptability, seasoned professionals bring a different kind of skill: the wisdom to ask the right questions. This balance of experience and curiosity is key to driving innovation forward.”Engaging Overlooked Talent“The bank in the Philippines found a surprising strength in its mature staff. When engaged and empowered, they contributed significantly to innovation, proving that tech adoption isn’t about age but about the opportunity to learn and apply.”_________________________Connect with Us:Host: Vince Chan | Guest: Steve Monaghan______________________--**Chief Change Officer**--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.100,000+ subscribers are outgrowing. Act Today. --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.12 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>140,000+ are outgrowing. Act Today.<<<
Chapter 1: Who is Steve Monaghan and what does he do?
Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Our show is a modernist community for change progressives in organizational and human transformation from around the world. Today, I'll be chatting with Steve Monaghan.
I first met Steve back around 2015 or 2016 in Hong Kong when he was the regional director at AIA, one of the leading insurance groups in the Asia Pacific. He was running a unique health technology accelerator at the time. Later, I invited him to be a venture coach and judge for the University of Chicago's first-ever Global New Venture Challenge, hosted right here in Hong Kong.
Since then, he's moved to Tokyo. We've called up a few times, both in Japan and back in Hong Kong. To me, Steve embodies authenticity. He is consistently successful and resilient in the face of setbacks. Largely because, I believe, he is always true to himself. He walks the walk and talks the talk. A real leader and an incredibly inspiring speaker. How could I not invite him to the podcast then?
Just how inspiring is he? Stay tuned for the next 30 minutes and you'll find out. Good morning, Steve.
Chapter 2: How did Steve transition from aviation to finance?
Good morning, Vince. How are things? I began my career in Australia, started as a commercial pilot and started to learn technology as a function of that. So in many ways, much of my career actually was founded then and there. I used to fly 22 hours a day and I'd run the company during daytime and fly at night.
And as a method of getting some sleep, I taught myself technology, how to use spreadsheets when that was a brand new technology. And it enabled me to get this advantage over my competitors that enabled me to, A, achieve my objective of getting sleep and be able to get quotes in people's hands immediately that would usually take most companies a few days to go and fulfill.
From there, I became more interested in the business side than the flying side. And then I started teaching financial institutions how to use spreadsheets and then started building models that people would build front ends around and payrolls, etc., And moved into the software industry and then moved into the hardware industry with Dell Computer Corporation.
I was on their startup team for Asia Pacific, developed pricing models, all sorts of things. So spreadsheeting really gave me my basis in understanding tech. And then, of course, creating hardware started to teach me about the importance of Moore's Law, Metcalfe's Law and Crider's Law, etc. So as I built the business across Asia Pacific, I moved from Australia into Malaysia.
And then my final role with Dell was in Korea. I set up the Asian Product Development Center for Compact Computer Corporation. That was also an equally interesting journey, working with some really brilliant people. My last role with Dell with Compaq was to set up the Indian business, which was failing miserably. And so I had a very kind boss that said, jump on a plane on Monday to India.
You've got to either fix or close the business. And closing is not an option. So I was given this tremendous opportunity to go and spend some time in India. And I went out to market, looked around and found out that who we thought our competitors were. Everyone said it was impossible that we can compete, but it made no sense because we were the world's biggest PC company.
How could you not be cost efficient? So after looking at how the market worked, how customers interacted with technology, et cetera, went back, financially modeled everything, worked out a better supply chain model to Dell, and then recreated the products to fit the financial model.
And when we did that, we zoomed from number four in the market and unprofitable to number one in a quarter and stayed that way for the next 10 years. That really gave me the basis for moving into finance. I went to Citigroup asking for help to redo my financial supply chain. They weren't so sure what a financial supply chain was, so I moved to Citi.
I developed their first mobile payments patent in 2001, something that most people use today. I called it multi-entry bookkeeping. Today, you call it a ledger, and we use barcode on the phone for mobile payments. Today, you use QR codes.
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Chapter 3: What motivated Steve to pursue diverse career paths?
Then from corporate investment banking in Citi, moved across, opening up a consumer finance division for a CBC bank, and then moved to Japan where I got to run a consumer bank and did a turnaround of that business during the Lehman crash. Then I moved across and became an entrepreneur, as I've done a few times before, actually. Ended up
Going to Singapore, where I became the first chief innovation officer at DBS, helped get them on the path to digital transformation. Then moved across where you and I met at AIA, where we ran the AIA accelerator and created Hong Kong's first unicorn. And then moved across after that to being an entrepreneur again and building the first insurance company underwriting system with AI.
And then after that, moved across, became a digital officer in Saudi Arabia for Rehab Bank, and then moved back here to Japan after COVID to establish really a focus on advisory investment. I've invested in a bunch of startups. And now starting my next big thing, which is a swing for the fences player to transform economies. No more small stuff.
Wow, it's fascinating to hear how your career journey has evolved, particularly how you've navigated from aviation to technology, software, and hardware, then deeper into various sectors of finance and entrepreneurship across different regions and countries. What's the core motivation that keeps you moving forward, especially in taking on vicious projects?
Very simply, learning. If I distill it down as I reflect on all of those transitions, it was really about this insatiable thirst for learning that I have. Not only that, but being able to work with others and inspire them to get that same thirst for learning.
So many of the folks that have worked for me have gone on to be quite wildly successful chief innovation officers of insurance companies, etc. And they've also transitioned industries. So one thing that you find that's common across everywhere is business is business and technology is technology. There's no such real thing as fintech or health tech or insurtech. It's all just tech.
And all you've got to do is work out how you use that toolset within your business practice. So every time and every transition, every country I went to, there was always something new to learn about that culture, some insight that they had that I didn't. So I learned as much going into each of those roles as I was able to bring to the table with that past experience.
Your personal website kicks off with a bold statement, learning the foundation for sustainable competitive advantage. He also openly mentioned, I've succeeded and I've failed always learning. Could you share with us some candid insights about times when things didn't go as planned?
Specifically, could you tell us about what you've learned from these setbacks and failures in your career and innovation projects?
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Chapter 4: How does being an outsider benefit leadership?
you really don't know. And so repeatedly, most people would be scared to do something new. Absolutely not for me. I thrive on it because I know I'm going to learn something and failure is just part of that journey. And that's well established in the business world. I've gone on to fail at many things, but each of those things has led me to the next big thing.
And I think that's the most interesting part of my journey.
You've really lived and worked all over the globe. Singapore, India, Saudi Arabia, Hong Kong, Silicon Valley, and now Japan. Everywhere you've been, you've been the outsider. How do you think this foreigner identity has shaped your approach as a leader driving change?
Part of that learning process was always I was the outsider. I was the outsider from a company perspective, from an industry perspective. I was the outsider from a cultural perspective because I was from a different country. I've been an immigrant in most of the countries since my 20s, right? So I've lived as an immigrant.
So I've always been the outsider, which gives me an advantage and a disadvantage. And the advantage is I have a view, an external view. I'm not tainted. I'm learning from the other side of the equation.
It's really insightful to hear how you've managed to change and overcome resistance in your roles. Could you elaborate on how you've tackled the challenge of people's natural fear of change in your work? In particular, when introducing new technologies or business models, how have you transformed a simple no? into know, knowledge, and acceptance. And what role did learning play in this process?
What I distilled it down from is the reason that people are fearful that they don't want to change isn't that they don't want to change. Actually, I think everyone wants to change. We love going on holidays to new places. We love having different meals every day.
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Chapter 5: How can you turn resistance to change into acceptance?
But if you're going to place a minefield in the middle of that journey and place everyone at risk, no one's going to go and make that journey to do that new thing. And that learning helped me distill into the reason that you get the most no's is because people don't know. They don't understand. They haven't learned. They don't really see what that new thing is.
My full role has been to turn a no into a K-N-O-W. So a no to a no and then into now. And that's really the role of any business person and any innovation officer or any digital officer is to actually go and make that happen.
The way that we made that happen, and it was particularly successful at DBS, where my partner in prime I'd worked with in Japan, and he was the head of talent management for DBS, a gentleman by the name of Tom Patterson. Tom worked in HR, and so we came up with this program of learning, venturing, and capital.
So how do you take learning so people are no longer fearful that they know that they can take advantage of that technology and transformation? and transform that learning into venturing, experiential learning, which is the most powerful form of learning, and then into capital for acceleration. How do you really start scaling things?
And when you bring that approach to bear, it works from the board to the branch. Really that focus on learning, making sure people understand, getting enthusiastic about change. And in the technology industry, change is a constant. We're forever planning to do things where the tech doesn't even exist today.
But we know we can get there and we know that we can actually have that growth mindset to go and scale the business off the back through either price cutting or taking advantage of cost reduction, etc. That doesn't exist in most industries. So that was a huge advantage for me coming from the tech industry into the financial services industry.
The moment you could start helping people understand how the tech industry worked and why their margins keep increasing while everyone else's keep decreasing was because they're driving depreciation costs as well as value in appreciation of features. So they're creating their own markets and then they're driving and making huge amounts.
So if you take Google, it was probably five or six years ago, increased the personal storage from one to two terabytes. has been stable for five or six years. But in reality, the cost per gig has actually plummeted. On average, it halves every 18 months. So their margins continue to improve while your experience of that service doesn't necessarily change.
Once you understand how tech works and apply it into new businesses, and you can give people that understanding and how they can use it as a multiplier, such as AI, then gives that growth mindset, which is very important for everyone in business.
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Chapter 6: What role do mature employees play in tech innovation?
I think when Steve Jobs introduced the iPhone, that he actually moved technology from something that only the young could do or that the 20 to 30-year-olds could do and made technology so simple to use that it actually engaged from three-year-old kids or three-month-old kids that could swipe a screen all the way through to grandparents that would previously not touch a device.
If you look at it in the same context now with what we're seeing with generative AI, it's now making technology so much more accessible to people that would have felt somewhat alienated by technology in the past.
So the bank that you refer to in the Philippines, one of the observations that I shared when I was working with their leadership team was that this is the first generation of technology where actually older people have an advantage because they know how to ask better questions.
And I think that's a very profound point because a lot of the younger kids may actually be somewhat disadvantaged because they don't know the right questions to ask. At this stage of generative AI, I think that makes quite a significant difference, as we know, with what we see in prompt engineering, etc. Older people do have an advantage.
Why do you think the younger people don't know how to ask relevant or right questions as opposed to the older members of the team?
In this particular instance, the average tenure of someone in that leadership team was ranging, I think, between 27 to 40 years. And they'd worked across every element of the business. So being able to ask the right questions, if you think of technology as not an individual light bulb switch, it's more a network.
So when you understand the network, you're in a better position to actually understand the implications and to craft your question in a way that takes into account some of the constraints of the network or some of the opportunities or accelerants of the network.
so that experience is pretty hard to come by it's why if you look at most ai what you want to do is take the experience and expertise and encode it and this is the perfect nexus of that you're getting people that would when they retired in the past would retire with all their knowledge Now we've got this enormous ability to encode that knowledge and take advantage of it and then pass it down.
Younger kids tend to ask simpler questions. They're still learning the basics and the ropes and trying to understand. They've generally got very limited exposure in terms of geographic exposure or business division exposure. Because I think the one other thing I've appreciated as I've got older is humans can't scale. We tend to specialize.
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