Being a CIO or a CTO is a tough gig. You don’t control a full P&L or even a revenue line. You only create economic value through other members of the executive team, who may not understand what you do and may have conflicting or competing objectives. You face a vendor community that primarily sees you through the lens of a sales target. Corporate functions in finance, HR and procurement that have their own agendas. In many sectors, you have stringent regulatory oversight and unforgiving regulators. And your team members worry that technological advances will render them irrelevant within a few years.
Political savvy grounded in game theory is existential if you want to assemble the fragile coalitions that progress requires. But that’s not enough.
I’ve been wandering around large technology organizations for decades — I remember frame relay and installing software from CD-ROMs. CIOs and CTOs who sustainably make progress draw on enormous reserves of character.
Here’s my hypothesis on the markers of character in a high-stakes business environment — and why they matter for CIOs and CTOs.
Duty: recognizing what you owe and discharging it. Will the rest of the executive team see you as prosecuting the shareholders’ agenda or your own?
Integrity: committing to understanding the facts of the matter. Will your team see you as doing the work to understand the options they present to you?
Judgment: choosing a course of action dispassionately based on the world as it is. Can you put anxieties and preconceptions aside when making “one-way door” decisions?
Fairness: giving other people their due. Will your team see you as sharing credit for successes and accepting responsibility for disappointments?
Courage: acting on your judgment despite personal cost. Will you fight for the resources required to reduce technical debt and protect the environment?
Enterprise: taking responsibility for making something happen. Will you keep going, no matter the absurdities and frustrations of corporate life? [1]
I’ve had the privilege of watching some senior technology executives handle reductions in force, reorganizations, brutal budgetary choices, strategic disagreements, tough vendor negotiations and stalled projects with class.
Character is not pleasantness or even conflict aversion, no matter what the zeitgeist believes or what they sell in airport bookstores.
Early in my McKinsey career, I joined a team supporting a massive, stalled IT consolidation. Coincidentally, the company had just appointed a long-time senior executive to lead this program.
He called the dozens of people working on the program together in a big conference room. He stood and said, loudly:
I have some homework for every employee of the bank in the room. Do some homework about me. Ask around. I’ve been around a long time. I’ve bought businesses. I’ve sold businesses. I’ve built technology organizations, and I have cut them in size as well.
When you ask around, people will tell you that I get done what I promise to do, and they will tell you that when people deliver I am very vocal in the bonus committee at the end of the year, and I get listened to.
We need to get this program on track. If you help me do that, I will speak up for you in the bonus committee. And if you don’t, I will speak up about that as well.
This was not pleasant. It may not even have been nice, but it manifested character. This executive understood his responsibility — the financial health of the institution demanded the hundreds of millions of dollars we would all save. He quickly grasped the gravity of the situation and declined to console himself with happy platitudes. He acted to address the biggest problem, an uncommitted team, and he promised astringent fairness at year end.
And sadly, I have sometimes seen the opposite.
For all these reasons I was thrilled to talk with my partner-colleague Ramesh Srinivasan about leadership and character in the executive suite, how that intersects with the age of AI and what that might mean for CIOs.
Leadership as a choice
In this section:
Leadership means accepting accountability for outcomes that others deliver, and exercising it is a choice
The Bower Forum has put 800-plus CEOs through a learning program over sixteen years, and the work became a book
The guest brings 32 years at McKinsey, mostly healthcare and life sciences, and has studied leadership at close quarters through the Bower Forum
James Kaplan: All right, this is James Kaplan with another Prosaic Times video podcast. I’m on video today with one of my favorite colleagues, Ramesh Srinivasan, who I’ve worked with on a whole bunch of stuff, mostly for clients in the pharmaceutical industry, and we’re gonna have a conversation about leadership and AI and about CIOs and how they engage with CEOs.
And the rest of the executive team.
Ramesh Srinivasan: I’m a senior partner with McKinsey, been with McKinsey for 32 years. The sector I know well is healthcare and life sciences within that, which is where James and I have done some work. But beyond that, I call myself a student of leadership. I play the role of the dean of the Bower Forum, which is McKinsey’s CEO learning program. We have had 800 plus CEOs who’ve gone through the program over the last 16 years. So it’s given me a chance to study leadership at close quarters. Based on that, we wrote a book called The Journey of Leadership, and I continue to study that topic.
James: Always a pleasure and it’s always exciting to be talking with someone who’s been at the firm longer than I have, especially now with Vik Malhotra retiring.
Let’s start off. Let me offer a potential definition of leadership. I’d like you to beat it up and see if you agree with this or do disagree with it. So I would define leadership as accepting responsibility and enlisting others in discharging that responsibility. Is that a plausible definition? What’s missing? Are there other definitions we should consider?
Ramesh: It’s actually a pretty good definition, James. When we wrote the book Journey of Leadership, Kurt Strovink and I, but also a couple of others, thought about this question about how do we define leadership? And we believe leadership is a choice and it’s not something that you exercise by default, but it’s good to be explicit and you assume the role of leadership when you actually have accountability and responsibility for the outcomes that others may be delivering on your behalf.
Leadership in an always-on world
In this section:
The core principles of leadership have held for three decades while the pace of change has not
Geopolitics, AI, and social media have made the role more dynamic and always on
Shorter CEO tenures through 2025 point to a harder job
James: Roughly speaking, our professional careers have spanned about the past three decades or so, a little bit more. We’re both getting older. Over that time you’ve been active in the professional world, how has the model for leadership changed? If at all?
Ramesh: I do think the fundamental model and principles, I think the good news is there have been many constants over these three decades. And so some of those principles I feel haven’t changed as much. But the fact of the matter is that the rate of change in the world has increased tremendously. You and I have talked about it, the geopolitics have become more complex today than ever before. Technology broadly speaking, but AI and Gen AI have also disrupted the world in a tremendous way. And so these couple of factors I feel have really forced leaders to be even more dynamic in the way they operate. So I think leaders I feel need to have a sense of purpose, a purpose that typically comes from within. So we call it the inside out model of leadership. So why do I do what I do? What gives me meaning? What gives me energy? What is my identity? Those I think need work so that I start from within. And I’m always on with social media now. What I say as a senior leader can be shared anywhere in the world. So I have a greater responsibility. It’s an always-on 24 by 7 role, so especially as a senior leader in the business or social impact world, I need to be ready for that, which was not as intense three decades ago, I feel, James. That’s probably been the biggest shift.
What I say as a senior leader can be shared anywhere in the world. So I have a greater responsibility.
James: What’s your view on the state of leadership today? If you look around at CEOs, you say most CEOs are pretty good leaders, most CEOs aren’t such great leaders.
Ramesh: I think most CEOs are pretty good leaders. So, in that sense, that’s an easy question to answer. But the fact of the matter is that CEO tenures are going down. So, investors and boards, at least that metric tells you that it’s harder and harder for CEOs to be delivering value to their stakeholders for long periods of time that they were able to do three decades ago. And so in that sense, it is becoming harder.
And so as human beings and leaders, CEOs, but also all of us need to really keep asking ourselves, are we ready for this challenge? Are we ready for this next level of changes, for this even more rapid world?
Inner-directed or other-directed?
In this section:
Riesman’s inner-directed and other-directed types frame the tension between purpose and popularity
One path starts by wanting to be liked and learns to speak truth to power; the other starts with a fixed aim and learns to hear competing ones
The answer is a balance that starts from a purpose that comes from within, then serves the stakeholders
James: You said something very interesting a couple of minutes ago about internal purpose. Last time we chatted, did I mention David Riesman’s book The Lonely Crowd from the nineteen fifties?
Ramesh: No, you didn’t. Tell me more.
James: Okay. It’s a fascinating book. It was written in, I think, nineteen fifty. And you would have thought it had been written last year. And it divides the world, or says that most people are other-directed. In effect, they want to be popular. They want to be liked. They seek harmony. And it’s said that some people are inner-directed. They have an internal gyroscope that often was set at a younger age and they have a set of things they’re trying to accomplish.
And sometimes I worry over time we’ve defined leadership as being too other-directed rather than inner-directed, though inner-directed can have its pathologies also, right? You can be a little bit of a heat-seeking missile, as I’ve sometimes been. Are the best leaders a combination of other-directed and inner-directed?
Ramesh: No, great question, James. Well, I’m the youngest of three kids and unfortunately my father passed away when I was twelve years old and I was a lonely kid and I really wanted people around me and so I did want everyone to like me. And I actually built skills to connect with people and connect with them quickly.
James: I’m sorry to hear that.
Ramesh: And it’s really as I grew more tenured as a leader, I realized that leadership is not a popularity contest. In my role as an advisor, sometimes I need to be able to tell people tough news. I need to be able to speak truth to power. And so to be an effective advisor is not to be liked by everybody. And it’s been a growth process for me. And as I’ve gone through that journey, inner journey myself, I’ve learned that I need to strike a balance.
And I need to go back to my own purpose. My own purpose is to bring hope, optimism, a sense of possibilities in an ever-changing world.
So the answer to your question and what we saw even with CEOs is it’s good to have a bit of balance, but it starts from within. It starts by being an inner-directed leader and having a clear why and being able to communicate that.
But then leaders and CEOs and CIOs and other leaders have an obligation to think about the different stakeholders, and making sure that the purpose, the vision is then serving the needs of different stakeholders. And when there’s a conflict, being able to do that in an effective way and making those trade-offs, that’s where I feel leadership is about, James.
So the answer to your question and what we saw even with CEOs is it’s good to have a bit of balance, but it starts from within. It starts by being an inner-directed leader and having a clear why and being able to communicate that.
James: Yeah, and maybe the best leaders figure out how to manage that dialectic. And my journey, however imperfect, has been the opposite of yours. Even as a small kid, I was hyper-inner-directed. I was like, God damn it, I’m doing this. And anyone else is welcome to come along for the ride. And I had a bad habit of, okay, I’m trying to do X. I think X is the right thing. And I wouldn’t realize that someone else was trying to accomplish Y. And maybe Y was a legitimate objective also, right? Even if it wasn’t X.
And how do we mediate between I want to do X and you want to do Y? And maybe both those things are okay and we don’t have to work across purposes to each other. That took me probably into my 40s to sort of work out.
Ramesh: No, that’s a beautiful journey. That’s what I feel, because if you keep listening to others, which was sometimes my challenge, then A, that’s not what the world expects of me. But also more importantly, that was not giving me joy and meaning. I define joy as things that I do every day, coming from the work of Mihaly Csikszentmihalyi, who wrote about flow. I’ve really reflected more on what keeps me in flow.
James: Flow: The Psychology of Optimal Experience is one of my favorite books. It’s like one of those books which I think everybody should read.
Ramesh: Absolutely. And that’s what results in creativity and innovation in the world. And on the other side, the work of Viktor Frankl’s Man’s Search for Meaning. When you have a great why, the how matters less and less. And just reading about his story, his work, I have realized that, for me, when I’m 80 years old, I really want to feel like I’ve had some accomplishment, even as along the way I’ve had joy and been in flow throughout, James.
Resilience and the choice of reaction
In this section:
Frankl’s Man’s Search for Meaning shows purpose sustaining a person in the worst circumstances
Resilience means reframing a problem into a challenge and a challenge into an opportunity
Frankl and Marcus Aurelius both place power in controlling one’s reaction, which no one can take away
James: Yeah, and a couple of thoughts. One is I read Man’s Search for Meaning in high school, but it’s a pretty good exposition of an inner-directed mindset, right? Which he obviously developed or sustained himself with in the worst circumstances imaginable. Right? And obviously infinitely worse than any circumstance you could experience in an office type environment, but I think that’s an example of the strength that a sense of purpose and a sense of inner direction can provide to you.
Ramesh: And maybe one theme there that was there in Viktor Frankl’s book, and also a theme we then borrowed and we expanded in the Journey of Leadership book is the notion of resilience. In today’s day and age, with all the changes, I think it’s critical for leaders to be resilient. And part of that is the ability to reframe. I often say how do you reframe a problem into a challenge and a challenge into an opportunity? Similarly, Viktor Frankl talks about when there is a stimulus, the biggest power that we as human beings and leaders have is we control our reaction to that stimulus. And nobody can take that away. That’s a choice that will stay with us till the day we die. And that’s been a very powerful notion I learned from him, James.
When there is a stimulus, the biggest power that we as human beings and leaders have is we control our reaction to that stimulus. And nobody can take that away. That’s a choice that will stay with us till the day we die.
James: Yeah, I tell that to people all the time. Someone else cannot invite you to the meeting. They can criticize what you wrote, they can be unfair in some way. They can’t make you be upset about it. Right? Only you get to control how upset you are about something or how you react to something. That’s tremendous amount of power. I just finished reading Marcus Aurelius’s Meditations.
It’s a fascinating book. And one of the things you take is this is written by possibly the most powerful man in the world, as he was writing, the Roman Emperor, right? And he is talking through the petty frustrations he has to deal with, and he’s like, there’s nothing you can do to escape the frustrations. You can be the Roman Emperor. And still be frustrated by this sycophancy or that flattery or that disingenuousness or what have you. All you can do, no matter who you are, is control your reaction to it, right? And that was an astonishing thing to me. But I suppose that’s why Marcus Aurelius was one of the five good emperors, and a much better emperor than, for example, his son Commodus was.
Do we talk enough about character?
In this section:
Business talks about character far less than the military does
One working definition: what a leader does when nobody is watching
A second test: how a leader responds under stress, which Navy SEAL training simulates
James: Let me ask you this question. Do we talk enough about character in the business world? Because there’s some part of me that thinks that everything boils down to character. And it sort of feels like an old-fashioned word. Are we embarrassed to speak about it? And should we be thinking and speaking about it more?
Ramesh: I think we should be speaking about it more. The military world actually understands it better. I’ve been learning about it from Admiral Eric Olson, who spent nearly forty years with the US Navy, Navy SEAL himself. And I think it’s actually quite critical.
James: Our mutual colleague, Charlie Lewis, is a West Point grad, right? And he was upset about something. He called me about it, he says, I have a ring that says duty, honor, country. He says, I take those very seriously. And it was one of the most striking and inspiring statements I’ve ever heard a colleague say. Right? It’s like, for him, everything comes back to that, right?
Ramesh: So I think character needs to be studied more. And one way to define character is what is it that leaders do when nobody’s watching?
So I think character needs to be studied more. And one way to define character is what is it that leaders do when nobody’s watching?
James: Also, he’s been on Prosaic Times, right? We had a great discussion.
Ramesh: Another way is to see what do you do under stress. The Navy SEALs do this by simulating stress. And the fact of the matter is with all the changes happening in the world, business leaders have to very often deal with stressful situations and how I respond in those situations I feel is a good test and a good definition of my own character.
Long on character: a working definition
In this section:
Executive teams may be long on character, but few have definitions, behaviors, measures, or experiences that build it
Six proposed components: duty, integrity, judgment, fairness, courage, and enterprise
Proposed additions: purpose, resilience, courage preferred over boldness, and curiosity
James: Right. So if you look at executive teams, are they often long character or short character?
Ramesh: What do you mean by a long character or short character?
James: A long character means we have a lot of character. Yeah, I’m talking — you remember I’ve served banks — you can be long or short a commodity, right? You may or may not think of character as a commodity, but your average executive team, do they have lots of character or do they have a shortage of character?
Ramesh: I’ve never heard this frame long character and short character. I think many of the leaders, especially the CEOs who come to the Bower Forum, I actually feel they’re long on character, if I were to use your definition.
James: Maybe a self-selecting sample.
Ramesh: It’s probably a self-selecting sample. They want to reflect more and they wanna explore more. But I often feel they don’t have definition around it, they don’t have specific behaviors that define it. They don’t have ways of testing and measuring, they don’t have ways of building character, creating experiences that build character. So that’s the struggle that I’ve seen.
How do you help them explain what they’ve been through and put some definition and terminology around it?
James: Yeah, that’s a fascinating idea. Okay, let’s assume you have a CEO who is taking character seriously, is willing to do the right things when nobody is watching. Then there’s a whole nother thing around how does that CEO foster character in his or her executive team and two and three and four levels down in the organization.
In my internal newsletter, I suggested six components of character. Let me run you through those. Tell me if you think this is missing anything. Duty. Integrity. Judgment. Fairness, giving other people their due. I was really bad at that when I was younger. Courage. And enterprise. How does that work for you as a definition of character? Does that resonate or not resonate? Or are things missing?
Ramesh: It resonates. The risk with some of these, like duty, for example, is that it comes with such heaviness that in a world that is changing so fast you need to figure out how you can be light and flexible, take initiative, take risk, back to your point about enterprise, so that’s a reaction that’s going through my mind. I’m a big believer on purpose. What is my why? And often that purpose is tied to my own crucible moments and my inner work and inner journey. So there’s something about that inner purpose and my why deserves some attention.
James: Yeah, as I define duty, I think I define it very similarly to the way you define purpose. I define it a little bit as what you owe, but I think you’re someone who sees his purpose as doing something for those outside of you. Right? You have a purpose that is not entirely endogenous, right? That it is service to others.
Ramesh: Correct. It’s a service to others but comes from within. I went to a public school in India where I paid five rupees a month and got an excellent, fantastic, almost I would say, world class education, and I felt like therefore I owed it to the system. And in part that’s what has driven my passion for education equity, later on, right? So to me the purpose, yeah, I could live with the sense of duty. Yes, it has a service to others and it has to come from within. I think the other is this concept of resilience that you and I have already started talking about. It goes back to my notion that character really gets tested when you’re under stress.
So to me the purpose, yeah, I could live with the sense of duty. Yes, it has a service to others and it has to come from within.
James: No, this is fantastic. Yeah, my takeaway here is even if you have senior executives who have character, I offer the hypothesis that institutions should be thinking more systematically about character.
Ramesh: I agree with you. And by the way, I love the notion of courage. Our colleagues published this book called CEO Excellence and one of the big ideas they talk about is being bold. I actually prefer the word courage to the word boldness. My sense is courage has a better, more robust and more rigorous definition. And then I love to use the word curiosity as well within the character, which goes back to your notion of evidence and really asking deep questions. We often talk about the five whys, and I feel like that’s so critical. Yes, we want to move fast, and yes, we want to react to changes in the world, but I think leaders need to ask the second order questions about implications of both the root causes and implications of their actions. And I feel like that’s a test of character as well.
Curiosity as a test of character
In this section:
Curious people make the best colleagues, and incuriosity makes intellectual integrity hard
Observation and orientation come before decision and action in Boyd’s OODA loop
Observing with limited judgment is a discipline, and asking questions can itself intervene in what is observed
James: Perhaps the biggest single discriminant for me about whether I enjoy working with someone is their curiosity. I love working with curious people. I love working with people who say, Yeah, gee, why is that? Explain that to me, right? And I would tie, and I thought about this, I would tie curiosity to integrity because I would argue it’s very hard for people who are incurious to have intellectual integrity.
Ramesh: I love that linkage. I love the intellectual integrity that I am really testing my own beliefs, my own frameworks against what’s happening in the world and I’m open to that debate and challenge as a component of character. I like that a lot, James.
James: Yeah, because if you think about strategy setting, right? John Boyd’s OODA loop, observe, orient, decide, act, which is, if you’re not observing and you’re not orienting, how the bloody hell are you gonna decide and act effectively, right?
Ramesh: In fact, my wife who is an educationalist, she often talks about low inference observations. When she goes into a classroom and she sees a teacher with forty students, her first instinct is just to observe. And observe, she might pick some great behaviors and some bad behaviors by teachers or students. Her instinct is to just pause the inference and the judgment or any decision making or comments, but really observe and observe with as limited judgment as possible for a period of time before then forming hypothesis and figuring out how to coach the relevant teacher or whoever is in the mix.
In fact, my wife who is an educationalist, she often talks about low inference observations. When she goes into a classroom and she sees a teacher with forty students, her first instinct is just to observe.
James: I’m really bad at that, not because I jump to the hypothesis. I’m like, why’d you do that? Why did someone say that? I always wanna ask the questions. I wanna understand why. So it’s hard for me to sort of sit back and not ask the twelve questions about why someone did something or why something happened, right? Which one of the things that fascinates me about the work we do and the work our clients do, which is say large enterprises are these incredibly complicated, interconnected machines, right? Machines with this, obviously tremendous human components. And just the ability to just like, okay, why did this happen? Right? Explain that, explain that to me. It’s sort of the part of me that was passionate about history, where you say, okay, gee, why did this set of events in the French Revolution happen, right? It’s like, why did this set of events in a merger or a business strategy happen or a technology strategy?
Ramesh: No, I love that curiosity about you, James. I think what I’ve learned from my wife is just the balance between getting those set of facts to just describe a system and then absolutely the asking the why you really dig into it.
James: Well, yeah. I’m not disputing her point because the challenge with asking so many questions, it’s like Heisenberg’s uncertainty principle. [2] Right, by asking the question you’re disrupting the experiment. So I’m not saying I’m right to ask all those questions. I’m just saying it’s hard for me not to.
Right. You’re observing the classroom. If you start asking questions, the classroom will go in a different direction. The act of asking the questions becomes an intervention.
Ramesh: Exactly. The first question becomes an intervention, even if it is asked from a place of curiosity and learning.
The CEO’s role in AI strategy
In this section:
The CEO need not be the AI expert but does need to understand the pace of disruption in the business
Three roles proposed: aspiration setter, systems thinker, and disruptor of governance functions that slow AI value
A fourth role: culture carrier; AI adoption moves at the speed of trust, and the CEO sets that tone
James: So let me bring this back around to AI for a second. What do you think the role of the CEO is in the age of AI, in pursuing AI strategy?
Ramesh: So the first thing is the role of the CEO is not to be the expert on what’s happening with AI, but I think the CEO needs to start with just an awareness of their business and what they’re trying to accomplish, their vision, their purpose. What is the level of disruption? And what is the pace of disruption?
As they then craft their strategy, how are they going to embed AI into what they are planning to do? And where is it that they want to experiment, where is it that they want to place some big bets? These are some of the critical choices. That’s what a CEO needs to be able to do effectively, James.
James: Yeah, I wonder if it’s three things. Tell me if you agree with this. First of which is the aspiration setter. Like people come and say, RPA is gonna change everything. Really?
I really think it’s easy to underestimate the transformative potential of Gen AI, largely because it allows us to process new types of data economically, process messier data and messier business rules economically than we could in the past. So one part of the CEO role is to set higher aspirations. And then a second thing I think is to be the systems thinker.
Right, particularly in bigger organizations, it’s easy to do local optimization. But the real value comes when you can connect across multiple businesses or multiple functions or multiple regions and truly step back and think about the system.
And the third is to be the disruptor. And in many places I look and see governance functions of procurement or HR or what have you, sort of being the decelerant for AI economic value because it’s just like, well, this is different. And I wonder if that resonates with you or things that are missing.
I feel like it can only move at the speed of trust. And that trust is really set, the tone is set by the CEO.
Ramesh: It absolutely makes sense. And there, a hundred percent, I agree with you that it starts with setting the right ambition and direction and back to our notion of courage and boldness that we are talking about, I think that is absolutely the CEO’s role and it needs to be done in a thoughtful way.
I think beyond that, the systems thinking part that you’re talking about, the disruption you’re talking about, I think all of that then needs to lead to capital allocation and resource allocation on where is it that you’ll have the highest impact.
So those are some choices that only the CEO can make. And then maybe that one I would add is there’s something around being the culture carrier, the tone setter, getting the right capabilities and skills around yourself that are technology enabled but still can drive business value. So maybe that’s the only dimension I would add, because when we look at the adoption and scaling of AI, I feel like it can only move at the speed of trust.
And that trust is really set, the tone is set by the CEO. So that’s the third role I might add to what you were describing, James.
Advice for CIOs
In this section:
This is the CIO’s moment, with CEOs and the C-suite coming to them for advice
Pick a few areas with the most business impact and partner with the more progressive executives
A May session in Chicago would take up character and culture for technology executives
James: So let me ask one final question. What advice would you have for CIOs aspiring to be better leaders and aspiring to influence more effectively the rest of the executive suite?
Ramesh: This is the CIO’s moment, James. CIO, CDIO, digital and analytics officer. All these folks have an incredible opportunity today by the disruption that AI, Gen AI technology offers to the world. Most of the CEOs and the C-suite is gonna come to them for advice. They are the technical expert, they have the credibility. So my advice to them would be: seize the moment. This is your chance. Of course, continue to learn to be at the forefront of whatever is relevant for your business and maintain the technical depth that’s expected of you.
But then really learn about where is it in the business you can deploy this value, make some choices so that you can really pick a few areas where you can show the most impact and treat the rest of the C-suite as your allies. Figure out where it is that you’re going to find some people who are going to be more progressive and partner with you to make things happen. So as you think about where to drive value, base it not just on the technology maturity and what’s possible, also on the business impact and also on the openness of the rest of the C-suite. So that as you help the enterprise, you’re really showing business value in partnership with the rest of the C-suite, and then bringing the whole, the CEO and the rest of the C-suite in this technology journey. That would be my biggest advice to them.
They are the technical expert, they have the credibility. So my advice to them would be: seize the moment. This is your chance.
James: Terrific. You just gave me a thought. So I think as you know, about every fall and every spring, we get together about sixty, seventy CIOs, CTOs, CISOs, and what have you. Next one is next week, but we’re gonna do this again in Chicago in May. And I would like you to come and lead a session on leadership character and being a technology executive. I think that would be a fascinating session.
Ramesh: No, love to do it. We’d love to do it. And maybe we do it with another CIO or a CEO who came from a technology background. That’s the format. So that maybe it’s a panel. Yeah.
James: Yes, we’ll figure out the exact format. Maybe it’s a panel or something like that. But this is something in between all the things about evals and platforms and what have you, which I’m very passionate about, as you know. I’d also like to have a discussion about sort of what’s it take from a character and a culture and a leadership standpoint to lead change around technology at this moment in time.
Ramesh: No, I love that. What does it mean to be a character builder and culture carrier as a CIO? That would be a cool topic to explore with a panel, James. Would love to do it. And maybe hopefully by May I’ll have a better framework as well on what defines character.
James: All right. I will recruit a panel for you. Terrific. Thank you so much, Ramesh. This has been great.
Ramesh: Thank you, James. Take care.
What is character?
Ramesh and I agree on a lot, and love working together, but you can see a little tension between our definitions of character. I see character beginning with obligations imposed by reality and one’s role: What do I owe? What is true? What does the situation require?
My six virtues govern action: duty identifies the obligation; integrity establishes the facts; judgment determines what to do; fairness recognizes others’ legitimate claims; courage bears the cost; enterprise gets it done. None of those requires the action to feel good — to you or anyone else.
Ramesh’s conception is more purpose-centered and inside-out. He repeatedly begins with why: meaning, identity, crucible experiences, joy, flow, resilience. The leader discovers an internally grounded purpose and then translates it into service to others. Character is partly about becoming the kind of person capable of sustaining that purpose through adversity.
My list gives conflict and personal cost a central place: courage specifically means acting on judgment despite cost. Fairness can be astringent. Duty may require doing something unpleasant. Ramesh worries explicitly that “duty” carries too much heaviness and reaches for resilience, flexibility, initiative, hope and optimism.
Humans have argued about character for millennia; forgive Ramesh and me for not settling the matter in a podcast. But intellectual tension yields insight. Purpose gives character an internal foundation: Why am I doing this? Duty subjects that purpose to an external test: What do I owe?
Any steward of an institution — anyone entrusted with consequential decisions — needs an answer to both.
Especially when navigating the lunacy of corporate life.
Footnotes
[1]: Character is a journey. I shudder at the man I was at 30. I was self-centered, callow and quick to anger. Looking at the list above, I’d say I did okay on a sense of duty, a commitment to integrity and on enterprise.
In contrast, I let anger and frustration cloud my judgment. And I gave no thought to fairness. I would roll over you (denying you your due) in the service of discharging my obligations as I saw them.
[2]: Strictly, Heisenberg’s uncertainty principle limits how precisely paired properties, such as a particle’s position and momentum, can be known at once. The effect I am describing is the observer effect: the act of measuring a system can change it.
