Three Questions Every Investor Should Ask About Any Management Team

In this episode of Motley Fool Hidden Gems Investing, Motley Fool contributor Rachel Warren talks with Cornelia Choe -- international leadership expert, former Morgan Stanley private equity investor, and co-author of The Panoramic Leader -- about the following:

• The hidden warning signs that a management team is operating on autopilot
• The three questions she uses to immediately assess whether leadership is truly on top of what's happening
• Why, in a world where AI has commoditized knowledge, the executives who can see around corners will be the ones worth betting on.

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A full transcript is below.

This podcast was recorded on Nov. 1, 2026.

Cornelia Choe: It's easy to fall in love with an investment thesis, and especially if we've invested in it. We want confirmation that we've made the right decision. But just step back and dare to look at the opposite opinion and just to see what we learn. It can only strengthen us, especially if we're long-term investors.

Rachel Warren: That was Cornelia Choe, co-author of the Panoramic Leader. I'm Motley Fool analyst Rachel Warren. In this conversation, Cornelia and I get into something that every long-term investor should be thinking about. Why the very instincts that make executives successful often become the thing that blinds them. We also dig into what the gap between how CTOs and COs think about AI is actually telling investors right now, and she shares the three questions she uses to immediately assess whether a management team is really paying attention or just running on autopilot. We hope you enjoy.

Welcome back to Motley Fool Conversations. I'm Motley Fool analyst Rachel Warren. Today, I'm delighted to welcome Cornelia Choe. Cornelia is an international leadership expert, the founder and CEO of the Leaders Alliance, and the co-author of the new book, The Panoramic Leader: How Great Leaders See Differently. Cornelia has worked in private equity at Morgan Stanley and other institutions previously investing in and supporting leadership teams across Asia, Europe, and North America. Today, she advises senior-level executives, heads of major multilateral organizations, and governments across five continents. Cornelia, welcome to the show.

Cornelia Choe: Thank you so much, Rachel. It's such a pleasure to be here with you.

Rachel Warren: I want to dive into your book. One of the things that really stuck out to me is you start with this scenario that I think maybe many in our audience would have experienced this idea of land a promotion, but the familiar playbook isn't working. Markets shift overnight, stakeholders multiply, and suddenly, maybe what felt like a good decision, maybe as likely a bad one. Why is it that the exact habits that get a leader to the executive suite often cause them to actually fail or struggle once they get there?

Cornelia Choe: That's such a good question, Rachel, and it's really central to our thinking because we go through life trying to figure out how to succeed. Finally, we find a map that works for us. We establish our thinking about how to do a good job, how to get promoted, and how to invest, for example. With the amount of change that we have in the world today, the map that we're using is very likely to be outdated very quickly. The biggest problem is that we don't know how. We have change coming from all directions constantly, whether it's supply chain disruption or tariffs, socio-political, economic shifts, technology and environmental shifts. If we are driving on a road that we think is a highway where it's all catered to us and very straight, yet we're on the open road with all the change around us, then we're going to get in trouble. That's essentially what a lot of leaders are seeing today.

Last year, we had the most amount of a record number of CEO departures for the second year in a row. These are very intelligent people with a lot of experience. What's really difficult today is that the information that we need to bring together to understand what's happening around us is really distributed in the minds of a lot of different people around us. For example, our finance department is dealing with varying costs of capital and financing costs that are changing, whereas supply chain disruptions could be affecting some of our operations or even our suppliers. The only way to really understand what's going on is to get up close to our stakeholders and to different people, understand how they see the world, and to bring their perspectives into a 3D understanding so that we can see more and make better decisions.

Rachel Warren: You were talking about seeing this mass exodus of leadership in certain areas. I wonder if you can talk more. Is that concentrated in specific industries? What tend to be the key drivers of those shifts from your vantage point?

Cornelia Choe: This goes across a lot of industries and company sizes. One of the problems is that it's really hard to lead today, not just because we're not able to see the whole landscape, but because it's hard to bring different people we're working with together, A, when we don't know how they're thinking, but B, because their thinking is diverging. To give you an example, according to a Grant Thornton survey, 39% of CIOs and CTOs believe that their companies are fully ready to adopt AI. Whereas only 7% of COOs thought the same. Now, this survey had a lot of overlap in companies, and that is a really big gap. To be able to bring together people who are thinking so differently, and in a lot of cases, diverging, it's an even bigger challenge than before. It takes a lot of humility to be able to question our own thinking when we've worked so hard to establish a formula that works and to find success.

As we mentioned, these are very intelligent and experienced people. There are two main pitfalls that my co-author, Marshall Goldsmith, and I see. The first is autopilot. This is when we think that what we assumed before that worked is still going to continue on. The brain takes up a lot of energy and calories, 20%, as opposed to 2% of our body weight. It makes sense to offload or to go on autopilot on as much as we can. The problem is this works in a world that's very stable, and it becomes very efficient in a tool, in that case. But in a world that is anything but stable, cutting back on this can help prevent what we call perspective blindness when we think that what we see is the whole landscape, whereas there's a lot more changing out there. On the other end, Rachel, we have an overwhelming fear of the unknown, where we're exhausted because we're dealing with unknown across the company, across our portfolio. We narrow our view and say, I'm not going to look outside. I'm just going to look at what I know and to manage that. Both are very tempting and make sense in a lot of situations. But for both investors and leaders of organizations and companies, it's a tool that can be overused in our attempt to deal with so much change around us.

Rachel Warren: It was interesting. You mentioned that one of the key factors you've been seeing is C-suite executives struggling with adapting to the world of AI, as we are seeing the pace of change happen in a way that maybe we haven't seen before. Maybe you could talk a little bit more about that. I find that a really interesting point.

Cornelia Choe: AI is affecting different departments and different stakeholders in different ways. For example, you have a CTO who might be very excited about what this could bring to the company, and they're looking at the power of the technology, whereas you have the CHRO, for example, who might be looking at how that translates into effects on people and what their apprehensions might be within our company. It's this translation that's the most difficult. A wonderful example of getting through this by really taking a deep dive into our companies is Piyush Gupta, the former CEO of DBS Bank. He really operationalized panoramic leadership within DBS, not because he knew what panoramic leadership was at the time. The book hadn't been published yet, but he provides an excellent example of how he was able to implement this into his company and adopt AI throughout his organization. He did this at four different levels, and at the first level, he created opportunity for all employees to surface ideas to senior management, and they put a lot of investment and funding behind these ideas. They knew it wasn't just a symbolic suggestion box.

Secondly, customer journey leaders were asked to bring something meaningful from outside the company, whether it's from a competitor or from a completely different industry, whether it's a practice or an idea, into the bank. This was written into their KPIs. It wasn't a choice to be more panoramic in our thinking and what we see.

Rachel Warren: The entirety of your book is centered around this idea of panoramic leadership. I think it begs the question, what are the traits of a panoramic leader? How does that tend to differ from how an average executive might function?

Cornelia Choe: Panoramic leaders are able to see much wider and to understand a lot more perspectives. We actually have three steps in the book called The GEM Process to help you become a panoramic leader. The first step is called Get UpClose. To ask yourself, who's not at the table, and to be able to see very wide. For example, Satya Nadella, when he became CEO, he didn't come in with a strategy deck saying, I have the answers. He went on a listening tour, and he listened wide, and he asked himself, what can I learn from everyone? He talked to managers, employees at many different levels, customers, partners, universities. He was able to create a strategy panoramically after listening to many different stakeholders. The second is to go deep, whereas in the first step we went wide.

Here, we go deep to establish meaningful bonds. To continue on with the example of Satya, he spent his weekends about a year ago, in fall 2025, studying start-ups and how they build products. At a start-up, he saw that everyone was sitting at one little table, and everyone involved in the product was altogether discussing it at the same time. He said that Microsoft's size had become a massive disadvantage. He was able to create the relationships to get up close, whether it's talking to founders or to be reading about them. He was able to establish the bonds and to really take a deep dive into them. Then, lastly, map your evolving perspective is the third step. What did Satya do with the knowledge that he got about start-ups being at one small table together? He created a commercial team where he combined engineering operations and finance together with sales and marketing, and they had shared accountability, which is somewhat similar to what Piyush Gupta created at DBS. He wanted to tighten the feedback loop between what customers wanted and how Microsoft delivered on it. These are the three steps that anybody can take, whether you're an investor or a leader or a manager or an entry-level employee to be able to get up close and understand more of what's happening around you and to rewrite your map so that you can see much clearer about the world around you and to make better decisions.

Rachel Warren: We focused a lot on these hallmarks of panoramic leadership and intelligence, but I wonder taking a look at the flip side of that. What are the most common strategic missteps that ultimately hurt long-term shareholder value and, of course, the company?

Cornelia Choe: Traditionally, we wanted leadership to know exactly what was happening. We have an image of the strong leader who says, I know exactly what's happening. I got everything under control. Ironically, today, that is a very clear sign that someone isn't looking panoramically, because when we do understand what's happening, that only lasts an instant. Things are changing constantly on a daily basis. As soon as I hear a leader say, I know everything that's happening around me, I've been doing this for a long time. Trust me, I get really worried. What I look at in companies, and especially in leadership, is three questions. Does leadership understand its stakeholders? Can they anticipate change faster?

Because when you understand your stakeholders, you have so much more information about what's happening around you. Can they articulate an opposing view? Because if they can't articulate this, then they don't understand it. Secondly, is management updating its assumptions? Are they learning or are they confirming? Again, when I hear someone say, I've been doing this for a long-time. I know everything there is to know about this, I'm the expert, then again, I get very worried, and I start looking even deeper into what management is thinking and what's happening in the industry and how the company fits into that. Then lastly, does management notice weak signals? Because a lot of change starts as shifts in customer behavior or supplier concerns about supply chain and other indications. The sooner we can see these, the more we can see around corners and being able to see that in a climate that is shifting is so important and gives us so much more of a magnifying view that we need today.

Rachel Warren: For investors in our audience who are evaluating corporate governance, looking at company leadership as they're determining the right choices for their long-term portfolio, what are some of the ways that shareholders can look at a company's leadership team and tell if they're operating on autopilot versus actually practicing some of those hallmarks of true panoramic leadership?

Cornelia Choe: I would look at investor communications, and there is always one very clean message that companies give to investors and to their stakeholders. But behind that are probably 10 different opinions even within the company and certainly amongst the shareholders. I would look at communications and if I can get up close to customers, to research online to see what they're thinking, to see if that correlates, because it might be that management and senior leadership aren't aware of what's happening, but it might also be that there are many different opinions within the company, of which many are important, but we don't get access to. Being able to do that legwork and to look much wider than we had before is so important today and being able to see more of what's going to help a long-term portfolio succeed.

Rachel Warren: You spent years in private equity at Morgan Stanley evaluating leadership teams across Asia, Europe, North America. Of course, today, you advise C-suite teams across borders. When deploying capital, what are some of the indicators that a management team has the agility to handle global change to scale across different geographic markets? What are also some of the mistakes they tend to make in those expansions?

Cornelia Choe: In the past, when the world was a lot more stable, my default would be look at what they've done in the past, and that would be a good indicator of telling us how they'll react in the future. The problem is we've hit an inflection point where what got you here isn't going to get you there in the words of my co-author in a book that he wrote, what we've learned so far may not be applicable going forward, and the level of change we see today might be the slowest level of change we see for the rest of our lives. To pinpoint a leader or leadership team that's able to rewrite their assumptions and do the heavy lifting of not going on autopilot, but constantly keeping the pulse on the market and to be able to understand a lot of different opinions, what's happening in America, but also what's happening in China? How do they think and to be able to put that together on an ongoing basis, that's a new skill that leadership needs that isn't taught in schools, generally, but is going to be so crucial going forward because you can be successful in the past, but going forward, it's going to take a lot more agility.

We look at AI, it's really commoditized knowledge. Everyone can get access to very deep level of knowledge very quickly. Being an expert isn't going to help differentiate us going forward. It's being able to know which knowledge and of all the data we get from AI, which data is the most important. What is the context around the data? How does it fit together? What does that mean for us? For people who are able to put that information together both when they talk to different people and when they look at a lot of research, are the ones who are going to be able to see more around corners and what we're going to be in store for 1, 3, 5 years from now.

Rachel Warren: Succession planning is also something that's notoriously difficult for major enterprises. I wonder how does that play as well into this concept of panoramic leadership and intelligence, when leadership is maybe, training other senior leaders to take their place down the line. What does that look like?

Cornelia Choe: Succession planning is more of a long-term exercise than a lot of people think. It's very tempting to say, there's somebody that I trust and I know they're going to carry on this wonderful work that the company is doing. Equally important today is to say, what's happening in the future. The skills that we've needed up until now, are those the most important skills for the next 5-10 years, for example. What do we need for our company? Because the situation we're in today could be completely different a year or two from now. But the problem is we don't know how. To be able to see what skills we need in the future and to be able to update who we think would be most successful in leading a company through the succession is going to be a new thought process that we haven't had to think about before. Being able to be flexible, and again, it's not up to one individual to make this decision. To be able to explain that and to get buy-in from the board or to be able to share our thoughts with a lot of people around us is both going to make the choice of a successor more long-term, and also the integration of that successor once they do start their new role, much more successful.

Rachel Warren: We've talked a bit about, of course, the gem method, this idea of panoramic leadership. But I'm curious what led you to write the book with your co-author, and maybe you can also talk us through some of the book's other core themes?

Cornelia Choe: Sure. I've known Marshall, my co-author, for a while, and we realize that we're some of the only people bringing very different people, leaders who think very differently together to solve their problems together. When you talk to people who see completely opposite of you, they're able to see your blind spots. It's such a gift to have them look at the problems, you're struggling with and to say, I see it completely differently. I hear leaders say all the time, I've never thought of that, but I've seen that you've done it and you've succeeded, so I'm going to try that myself. It's so helpful in being able to get more options and create more flexibility and maneuverability for ourselves in the future. He came up with the idea of writing this book together because, again, the skill of being able to integrate a whole range of information and opinions around us and to be able to choose what's the most important. How does this fit together and which information am I going to accept versus put on hold is something that we want to share with everyone so that they are able to do this going forward. That's how the idea of the book came about. We haven't looked back since then.

Rachel Warren: I wonder in the journey of researching and writing this book, what was maybe one of the most surprising things you've discovered about human behavior or leadership?

Cornelia Choe: The most wonderful interview I've had is with a wayfinder whose name is Punua Tamaehu. He led a traditional sailing boat from Tahiti to China, which is more than 12,000 miles. At one point in the journey, the sail had torn because of very inclement weather, and they were barely advancing and very worried that their supplies wouldn't last until they got to the next port. Punua was the captain, and he's sitting here taking his glasses on and off and wondering what on earth to do, turning his glasses will burn his hands. He comes up with this idea where he breaks the arm of his glasses which is the part that connects the frame behind your ear. He snaps that off, and he sees the needle that he needs to fix the sail. He sharpens one end of it, and very soon they're going at full speed towards their destination.

When I thought about solutions, up until then, I always thought, we need to create solutions. We need to build something. We need to create a coalition. It just goes to show solutions can be really right under your nose. You just have to see them from the right perspective, and that really brought home how immediate and real this can be. That was the most amazing interview we conducted because wayfinding is very similar to panoramic leadership. When you're out on the water without instruments, you have to feel the currents and the ocean, the swell, as they call it. Watch the animals to see which way they're going, look at the color of the clouds, and they all give you different information. Again, the question is, how do I bring this information together so that I can see much further so that I can see the island and my destination in my mind and make good decisions, and our survival can depend on this. Being able to do this is a talent that we're going to need more and more going forward.

Rachel Warren: It's a wonderful story and the wonder of human ingenuity. One more question for you as we draw to the end of our time together today. If a listener or viewer could walk away with one or two core lessons from the panoramic leader, what would you want those to be?

Cornelia Choe: It's easy to fall in love with an investment thesis, especially if we've invested in it, we want confirmation that we've made the right decision. But just to step back and dare to look at the opposite opinion, and just to see what we learn, it can only strengthen us, especially if we're long-term investors. The one advice I would say is, don't be afraid to question yourself and to get up close and to learn about opposing viewpoints, which it's easy to say, but it can be difficult in a world where we are already overcome by the unknown or we're already exhausted. But to start with small steps and to be able to increase our curiosity, we have something called courageous curiosity in the book, and that's so helpful in these small steps in a time when we feel overwhelmed because curiosity can give us something to be excited about and to look forward to and can also lead to a lot of understanding that gives us a much wider view than the one we started with.

Rachel Warren: Thank you so much for that. To those who are listening or watching, check out Cornelia's new book, The Panoramic Leader: How Great Leaders See Differently. Thank you so much for joining me today. It's been just a pleasure to speak with you.

Cornelia Choe: Thank you. It's been such a pleasure, as well. Thank you, Rachel.

Rachel Warren: To see the full interview, go to our Motley Fool Conversations YouTube page. As always, people on the program may have interests in the stocks they talk about, and The Motley Fool may have formal recommendations for or against, so don't buy or sell stocks based solely on what you hear. All personal finance content follows Motley Fool editorial standards and is not approved by advertisers. Advertisements are sponsored content and provided for informational purposes only. To see our full advertising disclosure, please check out our show notes. For the Motley Fool Hidden Gems Investing team, I'm Rachel Warren. Thanks for listening. We'll see you next time.

Rachel Warren has no position in any of the stocks mentioned. The Motley Fool has positions in and recommends Microsoft. The Motley Fool has a disclosure policy.