Chief Change Officer
#119 Steve Monaghan: From Pilot to AI Investor and Banking Trailblazer – Thriving Through Career Change
Tue, 24 Dec 2024
From the Cockpit to the Boardroom: Steve Monaghan’s 30-Year Journey Tokyo-based Steve Monaghan began his professional life as a commercial pilot before soaring into global finance. Over the past three decades, he’s driven innovation in banking and tech, reshaping industries across Australia, Tokyo, and the Middle East. His past roles include Chairman & CEO at Gen.Life, Chief Innovation Officer at DBS Bank, and Chief Digital Officer at Riyad Bank. Today, he holds key positions with RAKBANK, FinMir.ai, and several cutting-edge startups, making him a transformative force in the financial world. 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.EdTech Leadership Awards 2025 Finalist.18 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1.5% Podcast.Top 10 US Business.Top 1 US Careers.>>>170,000+ are outgrowing. Act Today.<<<
Chapter 1: What inspired Steve Monaghan's career journey from pilot to AI investor?
Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chan, 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 Neo-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.
Good morning, Vince Hellthings. 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.
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Chapter 2: How does being an outsider influence leadership in diverse cultures?
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?
There's been so many failures. I'll start at the beginning. When I joined Dell Computer Corporation, I had gone through a three hour interview where the national sales manager had picked apart my resume. I was joining as a product manager and he basically challenged every line in it. And at the end of the interview, he was so frustrated because he really didn't want to hire me.
He said, I can hire someone with 10 years experience. Why should I hire you? And I said, if I had 10 years experience, I wouldn't be applying for this job.
about two months later i'm sitting in the office at 11 p.m working on this monstrous multi-spreadsheet model that generates pricing once a month and i put my head in my hands and i thought oh my goodness i've oversold myself i really just didn't think i could do it but i went back and i read every single book i could on pricing accounting evaluation everything and i went in a very short period of time went back
rebuilt all of those models. Instead of making them just disparate pass-offs, I actually integrated them all, created configurators in Excel, started being able to do forecasts instantly, which was something that would take days usually. And then I started to look at how you would use for technology the way it's really meant to be used is to arbitrage time.
So how I could actually get a time advantage with my competitors, exactly what I'd done in aviation. So for me, and that experiential learning is the most powerful form of learning, was actually became the foundation for everything that followed. So it's a little like riding a bike. You can study it all you want until you actually apply it and put it together and get on the bike.
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 develop 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.
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Chapter 3: What role does learning play in overcoming the fear of change?
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 terabyte.
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
The motto of a podcast is make your laws of change. Steve has shared his own laws of change on his website, which I'll link in the show notes to those interested. He outlines three core principles. that change is always met with opposition. that implementing change requires a forceful effort. And third, that the larger the organization, the greater the force needed to enact change.
These principles aren't just relevant to organizational shifts. They apply to personal transformations too, such as career changes, something many of us are facing today. Take the first principle. Change is always opposed. If you are in a stable job with a decent income, why risk what you have for the conservancy of change? The second principle states that change requires force.
Whether it's due to layoffs or needing to relocate, the push and pull factors must be compelling enough to drive the change. Finally, similar to large organizations needing greater force to change, the higher you are in your career, the more you have a stake, and the stronger the impetus needed to push you through a transition. People generally resist change.
less is stressed upon them unexpectedly and without clear reasoning, logic, or alternatives as many experienced during COVID. However, if the conditions for change are managed well, involving and consulting those affected throughout the process, people can and will embrace change. Don't you agree, Steve?
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Chapter 4: How can older employees contribute to innovation in tech?
Chapter 5: What lessons can be learned from failure in a career?
So speaking of innovation and change and how it's sometimes resisted or embraced, you and I previously discussed an interesting case involving a bank in the Philippines. You mentioned that a particular segment of the staff there, the more mature, often overlooked group, actually contributed significantly to innovation efforts after you engaged with them.
I wanted to bring this up because there's a common belief in the tech world that older employees might not be as tech savvy as their younger counterparts. which can lead to ageism in the workplace. From your experience, can you share how you've seen mature employees contribute to innovation? And what are your thoughts on overcoming this legacy mindset that sometimes holds back valuable talent?
Sure. Actually, I'll start back earlier.
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.
And 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.
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Chapter 6: How can organizations manage resistance to change effectively?
Chapter 7: What are the core principles of successful change management?
How do you address the stigma or reservations that some might have about mental health in a high-pressure environment of startups?
I think it's very common. My response to folks that have that issue is saying it's very simply you have the wrong investors. I think that... If you deny people the ability to share, you're actually being part of the problem and actually more likely to lead to the failure of your investment than if you actually have a tolerance or more importantly, an alertness to what's going on.
When you see something going wrong in the business, the first thing I ask is always, how are you feeling? And I've had many entrepreneurs that have run, these are like quite well-funded startups that come back and say that you're the only person that's asked that question.
And if they don't have that outlet, then the chance of that mental health issue either spiking or becoming quite serious actually increases. Everyone knows that founders often suicide. I don't want any of my founders to suicide at all. That would be the worst possible outcome for the company as an investor and for me as an individual.
And I think that we need to be far more open to actually being empathetic. If you look at it, going back to ESC, it's one of the core principles of everything to do with customer interaction and with founder interaction. That emotional quotient is the foundation of everything that we do in life.
If you look at, there was a book written by Paco Rabanne many years ago, which I took to heart, is why people buy. And they make decisions with emotion, justify with logic and take action when it's easy. ESE. This is what drives trade and economies, etc. And the most important, at the end of the day, this is all about people and people map.
There's a really important point to emphasize. Mental health issues are not exclusive to entrepreneurs. They affect anyone, from entrepreneurs to employees to CEOs. I've personally faced mental health challenges three times myself, with two of those occurring during my time in corporate roles. It's something many of us might encounter regardless of our positions.
I asked one of my staff to take leave because it was very obvious that they were having mental health issues. And that leave made a world of difference. And that person went on to become very successful. And I won't narrow it any further, but was very successful in the career that followed.
And that person stayed working with me for quite some period of time before they left and found a bigger and better role. If you don't give people that opportunity to get back in balance, then I think that everyone loses.
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Chapter 8: How does generative AI change the landscape for experienced professionals?
Number five, empower people to own the change process. This approach helps eliminate their fear and can drive change more effectively and extensively. Number six, mature and experienced employees bring significant advantages in the era of AI.
Their first-hand experience with workflow pain points before technology intervention places them in a unique position to integrate technology seamlessly and enhance processes with a human touch. Number seven, pay attention to mental wellness, whether it's for employees or entrepreneurs. Everyone can be affected by mental health challenges in one way or another.
Number eight, maintain a balanced reading portfolio. It's essential for staying informed, curious, and effective in continuous learning. Until next time, take care.