Abhi Dhar has had a rich career journey, from serving as chief digital officer of a Fortune 50 company to co-founding a tech startup. In his current role as executive vice president and chief information and technology officer at TransUnion, he\u2019s responsible for all aspects of the company\u2019s technology, including strategy, security, applications, operations, infrastructure, and delivery of solutions that support its global information systems and associates.\n\nJust as notable as Dhar\u2019s career credentials are the quiet calm and genuine humility that mark his leadership style. When we spoke for a recent episode of the Tech Whisperers podcast, we explored his vision around transformation and his ability to operate with a business-first, customer-first, and people-first mindset. Afterwards, he shared some more advice for up-and-coming digital leaders and explained why it\u2019s worth choosing to do the hard things. What follows is that conversation, edited for length and clarity.\n\nDan Roberts: You\u2019ve been a C-level executive for a Fortune 50 company, a startup founder, and on the board of airline. What are the benefits of these diverse experiences, and how have they positioned you to be a better CI&TO for TransUnion?\n\nAbhi Dhar: You look at business from all different sides and you realize that businesses are just these contraptions that are supposed to generate cash and cover their expenses and create profit and pay back their owners. And hopefully the contraption itself is of value so the owners get more value out of it. That\u2019s capitalism.\n\nWhen you\u2019re in a Fortune 50 corporation, you realize that it\u2019s this enormous contraption, but it still does the same thing. And when you\u2019re raising a million and a half in seed capital, and you\u2019re trying to build this contraption, it\u2019s still the same thing, just at scale. That just burns an owner\u2019s or a founder\u2019s mindset into you, and it gives context to decision-making. So does being on a board. This whole notion of \u2018Somebody\u2019s money created this thing and you owe them something back\u2019 becomes very important.\n\nIt also has helped me spot talent. There are people who, when you have a conversation like this, they get it. Then there are people who are just compliant. They\u2019re an organizational component. They\u2019re not mission people. You need them, but they\u2019re componentry, not value creators.\n\nWhat are some of the challenges startup founders or those working in small companies have when they move to big, legacy corporations?\n\nBig corporations, especially public corporations, have an established business model. You have risk and audit and all of these people trying to make sure that nothing wrong happens. This thing is working, it\u2019s generating money, let\u2019s not mess with it.\n\nA lot of startup founders, when they join a corporation, get frustrated. They\u2019ll criticize it constantly: \u2018I can\u2019t do this, I can\u2019t do that, I can\u2019t innovate.\u2019 Yes, it\u2019s a tanker. You were on a speedboat. They\u2019re two very different things. Don\u2019t criticize the tanker for being a tanker. It does something. It creates a value. If we want to change something, let\u2019s be very considerate about it.\n\nYou mentioned your ability to spot talent. You also have a reputation for developing talent and growing the next generation, including many leaders who\u2019ve moved on to become great CIOs in their own right. Why is that a priority for you? \n\nAt this point in my life, I\u2019ve realized that if you can harness the strange, undefinable characteristics of human beings, when they get fired up and work together, they can do magical things. That\u2019s how great things happen. So that\u2019s what I\u2019m focused on.\n\nThe greatest joy I get is when I hear stories about people like Greg Michelini, who was one of the people who asked a \u2018mystery question\u2019 during the podcast. There are 20 or 25 people in my career who are now CIOs of large companies, and as I look back, it\u2019s those stories I think about. It\u2019s this person who didn\u2019t think they could do something, and they did it and they\u2019re now a CIO and they look back fondly on what you did. Except you didn\u2019t really do anything; they did it.\n\nThe most successful CIOs make \u2018people\u2019 the first pillar of their strategy, and it seems like that is deeply engrained in your approach to leadership. How do you make it part of the culture of your organization?\n\nI\u2019ve never forgotten how hard it is to be a technologist. When there is a crisis, when a site is down, when a system is down, when a release is not going right, it feels like the end of the world. It is extremely stressful. And the people who deal with that stress the most are junior- to mid-level executives. These are people with small children. These are parents who are just grinding it out. And sometimes the systems we work on are used by people who are also going through these same things. This is humanity. That\u2019s what we\u2019re doing, and that\u2019s why it\u2019s so important for us to think about the culture and say people are not expendable.\n\nAs engineers, if we can\u2019t avoid something that\u2019s going to create troubles for ourselves later on \u2014 where we\u2019ll have to jump on a crisis call or do something that would cause a colleague to jump on a crisis call \u2014 we shouldn\u2019t do it. I can\u2019t write do\u2019s and don\u2019ts and FAQs about it. But I can appeal to people\u2019s desire to do the right thing and to work as part of a collective.\n\nYour senior vice president of global technology platforms, Deepika Dugirala, has described software development as a creative process, comparing it to \u201ccreating a painting, carving a sculpture, writing a symphony or making pottery.\u201d What\u2019s your take on that?\n\nIf you look at those people like Elon Musk and Steve Jobs and others who have created an insane amount of value, nobody would argue with you about whether or not they\u2019re creative. The people who become engineers, they\u2019re the fixers and the tinkerers \u2014 because they\u2019re creative. They want to make something. If we\u2019re not careful, we\u2019ll kill their creativity. Part of it comes from refusing to acknowledge that they\u2019re engineers. We keep referring to them as IT \u2014 not that anything is wrong with IT, but the function of IT is not engineering.\n\nYou\u2019ve said that the first time you became a head of technology you wrestled with imposter syndrome and had to prove to yourself that you could actually be the head of technology. How have you dealt with imposter syndrome over the years, and what\u2019s your advice to the rest of us?\n\nImposter syndrome is a real thing. I used to think, I have to go to all these CIO meetings because now I\u2019m the CIO, and I need to remind myself that I\u2019m the CIO. It\u2019s that constant worry of, am I good enough, can I do this job, what if something happens? Thankfully, I\u2019m sort of beyond that.\n\nI think one way I\u2019ve managed it is that, given choices, I choose the harder thing. And then I\u2019ll think, oh my God, I\u2019m done. But somehow, some way, some force carries me forward. People around me support me and I make it to the other side. And once I\u2019ve made it through, I\u2019ll say, I\u2019m never going to do that again. I\u2019m going to take the easy path. And sure enough, two days later I\u2019m back at it. And I\u2019ll be thinking, why did I do that? There was an easier path! Why would I join a board? Why did I do a startup? Why would I go to a financial services corporation when I\u2019m a retail guy \u2014 I don\u2019t know anything about financial services. This is so hard!\n\nBut somehow, we make it. And somehow, slowly, that little voice that says you can\u2019t do it starts feeling less important, because now you\u2019ve done it. The most important thing is, if you\u2019re completely devoted to the service that your role is supposed to provide to the organization and overly focused on it, then it\u2019s kind of like you\u2019re not even in it. It\u2019s not about you at all.\n\nYou are intentional about pushing people beyond their comfort zones. Could you speak to those across our profession who are climbing the ladder but can\u2019t seem to break through to the next level? \n\nI am an immigrant. I came to the US, didn\u2019t know anybody, and constantly wondered if I was good enough. By happenstance and luck, I ended up in situations where I needed help, so I sought out mentors and they helped me. Because of what happened to me, when other people are stuck and don\u2019t see how they can really progress as professionals, I\u2019m able to spot it.\n\nI remember having this conversation with Greg, telling him he needed to take the job at this Fortune 10 company and be responsible for our pharmacy systems, from a tech point of view and from a customer point of view and from a business point of view. I said, \u2018You\u2019re the best of the best. What are you doing running around here being like a bureaucrat? Go do this.\u2019 He was like, \u2018That\u2019s crazy. That\u2019s so risky.\u2019 And I said, \u2018Yeah, but you\u2019ve got it, man. If I did it, so can you.\u2019\n\nThere are multiple people like that, and it\u2019s not because I have some great foresight. It\u2019s just that I made a lot of stupid mistakes, and I can point out to people how that\u2019s going to end. So it\u2019s very important that I do that. That\u2019s also where I talk about \u2018flipping the script,\u2019 because a lot of people will say, this is the script. And I keep telling them, no, you\u2019re none of those things. You are this person who can do this by generating this much value because you understand this. Once you provide that clarity to people, they do great things.\n\nThe biggest success in my life outside of my family is all these great people. They are amazing CIOs. If they worked for me, and they\u2019re a CIO, I\u2019m telling you right now, I give you my reference: You send them into any battle, and they will win.\n\nFor more wisdom and insights from Abhi Dhar\u2019s leadership playbook, tune in to the Tech Whisperers podcast.