Feeling Fearless | Interview with Citi FinTech’s Carey O’Connor Kolaja

What is your greatest fear for the fintech space over next 1-5 years?

Looking ahead into the next few years, we need to ensure that the regulatory landscape keeps pace with the rate of technological innovation. The policies and laws that are governing our industry are protecting the expectations and needs of the past, not the needs of today or those of the future. Embracing the need to evolve regulation, protect the data that defines us, protect our identities and manage risk levels the playing field for society to participate in the financial system. We need to strike the right balance between controls and choice.


What advice would you offer to help other leaders be fearless?

The best advice I can give is to deeply understand yourself, what you stand for and what you believe in. We live in a world of contradictions, paranoia, uncertainty and perpetual change; to lead through it and above it you need a strong sense of self. It’s that strong sense of self that allows one to take risks, and then being fearless becomes as easy and natural as getting dressed in the morning.

To be a fearless leader includes a willingness to be imperfect, vulnerable and authentic, which means you have to be willing to make mistakes and to own them and, more importantly, share them. It’s beautiful that today’s speed of change and innovation is accelerating. The cycle of what matters today vs. in the future is growing shorter each year. For leaders, that means being able to move quickly through mistakes, which are inevitable when you take risks and act fearlessly.

As part of my journey to develop a strong sense of self, I read “The Alchemist” by Paulo Coleho once a year. It reminds me that fear is often a bigger obstacle than the obstacle itself. This is one of my favorite lessons. New pursuits require entering uncharted territory, but with any great risk comes great reward. The experiences you gain in pursuing your dreams will make it all worthwhile.


Tell me a little bit about what you do at your current company.

I’m the Chief Global Product Officer for Citi FinTech, a unit charged with ensuring Citi’s Global Consumer Bank rapidly adapts to – and also shapes – the evolving financial landscape. We design every product, solution and experience with a client-first mindset. Through our Open Banking and Canvas platforms, we’re accelerating the design and delivery of new solutions to address industry disruption and evolving client behaviors with a commitment to co-creating within and outside the financial ecosystem.


What’s the most valuable learning experience you’ve had – that is, one that lit a fire under you, inspired you, or caused you to make a change in your career?

At one point during my career, I was struggling to co-exist in an environment where I felt people were not always doing what was right for the company. I defined myself as “truth teller” but while I thought I was doing the right thing, a senior executive said to me, “Everyone has their own version of the truth, so stop being a truth teller.” That really resonated with me and going forward I began to reflect on how others were viewing the situation. I began to consider what another person’s version of the truth is and how it could or should potentially reshape mine.

What’s the best piece of career advice you’ve received?

About 10 years ago, I participated in a leadership immersion session and my coach told me to “always speak in the first 5 minutes of a meeting.” Before hearing that advice, I was uncomfortable with public speaking. I preferred intimate, in-depth discussions. I was worried about perception and optics and would opt to remain a quiet observer and lead from behind. That advice helped me find a way to break through my mental block because I realized that if you don’t you’ll never be given the platform to have a broader impact on others. So I started talking, and I haven’t stopped.

Another piece of advice that has stayed with me was from my boss when I worked at eBay. He encouraged me to follow the money, but not in the way you may think. He made me realize that many executives do not understand the economics of a business. As a result, many are unable to determine where there are inefficiencies and where they can make meaningful trade-offs when there is a downturn. In fact, it was in him that I found pride in being able to do more with less, in creating capacity to take on more, on balancing how to run a business at full-throttle with the ability to dial it back to “keep the lights on” when necessary.

What’s a skill or character trait that’s crucial to success in your field?

It is critical to have an insatiable sense of curiosity and relentless commitment to challenging the status quo. To change an industry, you must embrace change and stay informed of global, industry, market, regulatory, and most importantly consumer behavior trends.

You must be comfortable learning from others and have a desire to understand, to learn, to ask questions that don’t yet have answers and then work to solve them. Thinking differently is important and being able to see around corners is a gift, but it is paramount to have empathy for others. Empathy for your customers, your colleagues and the world at large.

Do you have a mentor? How did you meet them, and was it beneficial for you in your career?

Many of my mentors never knew I saw them that way. Those I have had the privilege to work with were amazing. I have always believed in this statement, “Leadership is about making others better as a result of your presence and making sure that impact lasts in your absence.”

There have been many members of my team and my professional and personal communities that opened my eyes, gave me feedback, took as much interest in me being a great leader as I did in them.

What’s the first thing you do when you get to the office in the morning?

I would turn this around on you and ask you…where is your office? I believe that work is changing and we are living an integrated existence. I don’t separate my office from my home or delineate between work and home hours. This requires that I set my own boundaries and define when I work and when I don’t. Each day is different depending on the demands of my integrated life, but there are a few constants. I always start the day by doing something for myself. I’ll workout, meditate, watch the sunrise, read, write – whatever I need that day to fuel my soul.