June 10, 2025

208. Ambiguity to Action: Tensions and Trade-Offs of Leadership and Communication

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208. Ambiguity to Action: Tensions and Trade-Offs of Leadership and Communication

Amidst constant change, clear communication is the key to navigating uncertainty.

How do you communicate with others when you’re confused yourself? For Rob Siegel, leadership isn’t about avoiding uncertainty, it’s about embracing the clarity that ambiguity can bring.

"What if ambiguity is the new normal?" asks Siegel, a venture investor and lecturer at Stanford Graduate School of Business. From rapidly evolving AI to ratcheting geopolitical tensions, every day brings a “crisis du jour,” he says. “I may like it, I may not like it. That doesn't really matter, but I've gotta get my team through it."

In his latest book, The Systems Leader: Mastering the Cross Pressures That Make or Break Today's Companies, Siegel explores how leaders today are “living in dualities,” caught between managing existing processes and adapting to emerging disruptions. “The sooner we get comfortable with [change] in the sense of ‘I don't have to like it, but I can deal with it,’ then [we can] lead our teams and give them the calm to know they can get through this.”

In this episode of Think Fast, Talk Smart, Siegel and host Matt Abrahams explore how to communicate effectively amidst constant change. From preparation strategies for spontaneous speaking to building trust through candid conversations, Siegel offers practical tips for communicating with clarity when nothing is certain but change.

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Chapters

00:00 - Introduction

01:49 - Adapting Leadership for Uncertainty

03:18 - Systems Leadership and Cross Pressures

04:40 - Communication and Context

05:26 - Framing Complex Ideas

06:21 - Innovation vs. Execution

08:11 - Leading Through Ambiguity

09:33 - Short-Term vs. Long-Term Focus

12:44 - Balancing Strength and Empathy

15:26 - Leadership with Humanity

16:42 - Engaging Students Effectively

20:00 - The Final Three Questions

23:41 - Conclusion

Transcript

Managing different tensions is critical for effective leadership and communication. My name is Matt Abrahams, and I teach strategic communication at Stanford Graduate School of Business. Welcome to Think Fast Talk Smart, the podcast. Today I'm excited to speak with Rob Siegel. Rob is a venture investor and like me, he's an instructor at the Stanford Graduate School of Business, but unlike me, who only teaches one class, Rob is a teaching machine. He teaches a lot of different classes, including system leadership, the industrialist dilemma, and corporations finance and governance. You might remember Rob from his first visit to Think Fast Talk Smart in episode 37 where we discussed his book, The Brains and Brawn Company. Rob has a new book out called The Systems Leader: Mastering the Cross-Pressures That Make or Break Today's Companies. Welcome, Rob. Thanks for being here.

[00:00:54] Rob Siegel: Oh, thanks Matt. It's great to be back.

[00:00:55] Matt Abrahams: Should we get started?

[00:00:56] Rob Siegel: Absolutely.

[00:00:57] Matt Abrahams: A lot has happened in the world since you and I last chatted on the show. In an era of rapid technological change and global uncertainty, how have you changed what you're focusing on with your students and what you recommend as they become new leaders in this new world order?

[00:01:11] Rob Siegel: One of the courses I teach, and have for the last eight years, is called systems leadership. It was a course that developed out of a conversation that Jeff Immelt, my old boss from GE, we had about leading in a world where every product and service is connected. And we realized as COVID hit and even coming out of COVID, leaders in particular in business, are really struggling with this kind of constant crisis and the speed with which technology is happening like AI. And we think it's really important that leaders see systems, they understand action and reaction inside of their company, as well as the company and its ecosystem. And so what we've been really focusing on is trying to help leaders make sense of the chaos that's around them. Try to find clarity and how do they lead their teams when it feels like everything is just constantly blowing up on us. We turn on our computers in the morning and it's, oh my goodness, what happened last night? How do leaders keep calm and get through those times? 

[00:02:02] Matt Abrahams: What's some of the advice that you give or some of the frameworks that you teach in the class and in your new book regarding how to handle all that? 

[00:02:09] Rob Siegel: We talk first about what I like to describe as unserious behaviors in a serious world, things that don't work, things where we see leaders being bombastic and outrageous at the expense of decorum. We see them focusing on trivial goals. And we try to get them to figure out what are the things that great leaders that we've studied, what do they do? And they kind of have a, what we call a product managers mindset, understanding customers, how products get built and go to market. We talk about living in dualities, understanding, how do we understand internal and external? IQ and EQ, how do we understand innovation and operations? And then in the book we highlight what I call five cross pressures.

[00:02:45] These things that seem to be pulling us in opposite directions that make it hard for us to know what to do. I look at setting priorities, innovation and execution. People, how do we lead with both strength and empathy? Sphere of influence. How do we understand internal and external? Uh, spend some time looking at geography, both local and global. And finally, purpose. You know, how do we balance stewardship, or statesmanship, or stateswomanship, with our own personal ambition? And we look at leaders that have visited us in the class, and that we've been able to study, and how do they handle those cross pressures? And try to lay out a path, a way of thinking, a framework that today's leaders, whether they're managing a team or a company, how can they follow and make that successful for them and their, their people.

[00:03:24] Matt Abrahams: I really wanna dive into some of those. 'Cause all of that is fascinating and I love that you have some very specific advice on how to manage that. I'm curious though, the role that communication plays in all of this, it seems to me that would be rather important. 

[00:03:35] Rob Siegel: Absolutely. And in fact, one of the things we talk about with our students is this aligned truth equals facts plus context. And facts are facts, but context is how we understand things. And communication's a big part of that. How do we help people make sense of what seems like constant craziness? And communication's critical, in written communication, on oral communications. What's it like when we talk one-on-one, like we're doing now, how do we handle small groups? What's it like when we're in charge of a large audience? And how do we make sure that our voice carries our messages in ways that makes things simple, but also gives people something to think about and hold onto. 

[00:04:10] Matt Abrahams: Do you have some best practices for some of those things? Like how do you take something that's complex and make it more accessible without dumbing it down to the point that it gets challenging?

[00:04:18] Rob Siegel: It's hard, and I think the first thing is kind of acknowledging it's hard. For me, I like to spend time thinking about an issue and looking at it from different angles and perspectives. In fact, all hard issues are nuanced, and like leaders today lead on nuanced issues in a world that seems to have very little time for nuance. I need to make sure that I'm looking at things from multiple perspectives and points of view. That also helps me frame it for the people with whom I'm communicating, and that also allows me to build empathy. Because even if I disagree with somebody, if I can understand where they're coming from, I can hopefully express my opinions, hear theirs, and then try to keep evolving my perspective on things. Communication's critical and part of communication, I would also posit as listening. Making sure that I hear others and really trying to understand root cause of what might be driving how they're viewing the world. 

[00:05:05] Matt Abrahams: You know, I often tell my students two things. I say communication is both operationalized empathy and operationalize leadership, and you touched on both. The fact that you have to take time to reflect and understand the intricacies and nuance before you communicate is really important. And part of that, as you said, is listening and then being able to articulate it in a way that's appropriate for the people that you're talking to, be it in a big platform or even in one-on-one interactions is really important. I wanna come back to communication, obviously in a little bit, but I'd love to explore some of these tensions that you talk about because this notion of managing these dualities is really hard. You talk in the book, and I know in your class, you talk about balancing innovation and execution and those can be loggerheads sometimes, right? Oppositional. How does one manage that? You want to execute well, but you also wanna be innovative and creative. How do you do that? 

[00:05:57] Rob Siegel: I think historically these things, if they existed inside of an organization, were in separate groups. So our colleague Charles O'Reilly and Michael Tushman from Harvard came up with this notion of the ambidextrous organization. And Robert Burgelman, our colleague, did a lot of work on strategic innovation in corporations. And the idea was that you had the people who made the trains run on time, and you had the crazy long hairs who innovated, and they would tolerate each other, and it was usually moderated and modulated at the top. Usually somebody who would deal with budgets and everything else. In today's world where technology is moving so quickly, I think it's important that we as individuals need to be able to do both.

[00:06:31] We need to be able to hit our numbers, but we also need to know how to manage innovation because the speed with which we need to get new technologies into our operations and into our products is happening so quickly. So we've gotta know how to manage a small team of three people and maybe trying to do something new, but we also need to be able to operate at scale. And whereas historically, that could be kept separate and you could build bridges between them, we as leaders, need to manage this duality. 

[00:06:55] Matt Abrahams: Absolutely. So it's speed and just being able to get your arms around what all the issues are. In a recent walk and talk, you and I did, we talked about how leaders need to be able to tolerate ambiguity in a way that perhaps they haven't in the past, and this is a, an area of interest I have around how we use ambiguity strategically. I'm curious for you to share with the listeners some of the things you and I talked about around this notion of managing ambiguity when things are changing, be it innovation versus execution. 

[00:07:23] Rob Siegel: What if ambiguity is the new normal, Matt? What if this is just the everyday state of affairs? And I think the ambiguities, like we don't know what's gonna come next. And it's almost like it's gonna hit us and we anticipate it, but I think it's being comfortable with it of, I woke up today, here's the crisis du jour. Okay, I may like it, I may not like it, that doesn't really matter, but I've gotta get my team through it. And I think it's that ability to say, I'm comfortable with this. I can think how to get through it, and we'll do our best as a team to get from where we started to where we need to get to. That's not comfortable for people. People don't like change. I mean, all the lies we tell at Silicon Valley about change is great. Embrace change. Change is constant. Yeah, that's true. But humans hate change. And it's happening faster and faster. The sooner we get comfortable with it, in the sense of, I don't have to like it, but I can deal with it, then it's our ability to lead our teams and lead the people around us and give them the calm to know they can get through this. 

[00:08:17] Matt Abrahams: When you and I were walking, you gave me the title of a paper I'm writing, which is the clarity that ambiguity brings. And the clarity is focusing on what I can control, focusing on what I need to message and how I need to message it. And I think all of us need to think about what it means to do our jobs, to hold the relationships we have, in a world where things are ambiguous and changing. And the notion that we are all by nature, risk averse is very true, and that comes into conflict with what the reality is, is that things are changing. So I like what you said, because it really does drive us to clarity when it comes to how we deal with ambiguity. I want to dig a little deeper going back to this notion of innovation and execution. Another tension that you talk about is the focus on short-term versus long-term execution. What are your thoughts on that and how do we deal with that tension there?

[00:09:04] Rob Siegel: I think part of it is if we think about things like capital allocation, how much do we make sure we spend and invest on both time horizons? Sometimes there's the tension of, do I invest in the current quarter or the current year? It's easy to say we have to do both, but we have to know how to manage both. And I think the short term, you know, we have to survive the short term to get to the long term, but if we don't manage for the long term, once we get there, we can be hollowed out very quickly. And we see that with great companies that spent too much time focusing on the near term and not thinking about the long term. And trying to bake that DNA, bake that mindset into the organization, I think that's really the job of the leader. And to make sure that people know that they've gotta be simultaneously delivering in the near term, whether that's days, weeks, or months or quarters.

[00:09:46] But also thinking about, what's my roadmap and am I delivering to it? Whether it's eighteen months out or two years out, some industries move faster, some industries move slower. Our industry in education moves historically very slow, and yet look at how quickly it's changing right now. Again, I'll go back to AI. AI does a pretty good job answering the problem sets that I assign in my finance class, and I've gotta make sure that I now have to test differently. I have to ask different types of questions, and that has to happen quickly. But I've also gotta be thinking when I teach the class next year, where do I think AI is gonna be? And the students are gonna use it anyways, whether I like it or don't like it is completely irrelevant. How do I make sure that I'm preparing for something twelve months from now? One, I don't even know what it's gonna be, but I've gotta be ahead of the curve thinking about it, knowing what's going on, taking in information from the outside and adjusting. 

[00:10:32] Matt Abrahams: You remind me of the saying, focus on not just the urgent, but focus on the important, and we have to, again, in terms of duality, be able to do both. You can't let one go without the other. And I always put from a communication lens, we have to reward and send and give feedback that affects the short term, but also have a mind what that means for the long term. And that's not just in the productivity and efficiency of an organization, that's just in the way we relate.

[00:10:56] Rob Siegel: Well, if we think about that in managing our people, we need to give them the hopefully specific enough guidance to know what we expect them to be able to do in the next few weeks or few months on KPIs. But we also have to be thinking about growing them in their career. We have to be thinking about are we developing them for their runway, is an expression that we should talk about in when I was at GE. Can they do not just this job but the next two jobs? And am I doing what I need to be doing as a leader to helping to set up the men and women who report to me, to make sure that they can take over my job and even the one after that. And that's that kind of near term and long term as well. 

[00:11:28] Matt Abrahams: One of the best bosses I ever had when I was working in the corporate world made me every six months turn in my updated resume. And the idea was that she wanted to see how I was growing and learning, and she said, your resume has to be ready because I want you to succeed at whatever's next if that's here or elsewhere. And I, I really took value from that. And what she was saying is, I want you to keep developing and I'm thinking about your future while also supporting you in your present. You know, in my strategic communication class, one of the first topics we discuss is the balance between warmth and strength. And I know you talk about the notion of balancing strength and empathy. What can leaders do to balance that out? Not just in their own lives, but in the way they interact with those around them? That's a, that's a really, again, tough tension. 

[00:12:12] Rob Siegel: There are a couple of great people that we studied on this one, and we've talked about her before, is a woman named Kathy Mazzarella. She runs a company called Graybar, used to be Western Electric. Most people haven't heard of Graybar, based in the Midwest here in the United States, plus or minus eleven thousand employees, twelve billion dollars in revenue, all employee owned. Kathy was described by somebody as an iron fist in a velvet glove. You know, she's one of these leaders, Matt, that when she walks into a room, we all sit up a little bit straighter because she's just that good and we know we need to bring our A-game. But she's incredibly human and she shows her human side to the men and women who report to her, but she also tries to see the human side.

[00:12:51] Now if somebody's not performing and not getting their deliverables met, that's not okay. But her first question is not, you know, I'm gonna beat this person up over it. It's like, why didn't they get it done? Is it, do I have a skillset mismatch? Or is somebody going through something at home, an illness, or a family member sick or something that's going on that I need to be aware of that she says might be impacting their performance? And so I think she balances both of those things. Another one we studied is Julie Sweet, who's the CEO of Accenture. Almost eight hundred thousand employees, you know, four billion dollars in revenue. They invest heavily in their labor force. They spend a lot of money training people on the latest technology. And what she will say is, look, we're gonna give you the tools to make it available for you to invest in yourself and grow.

[00:13:32] You need to deliver what you're gonna do today. You need to invest in yourself for tomorrow. My job is to make sure that investment and those capabilities and that education is available to you. She holds people to the task of you've gotta do it yourself. I'm not gonna spoon feed it to you, but I'll make sure you have the resources to get it done. And I kind of like that as well, because Kathy's a little bit more empathetic, but she's strong. Julie's a little bit strong, but also empathetic of, I've gotta invest in you and I know that, and I've gotta make that available to you so that you will actually continue to grow. And I think understanding that her people wanna be ambitious, that they want their careers to develop, that's a great win-win for her, for the company and for the employees.

[00:14:10] Matt Abrahams: I really like those two examples, and they highlight that in any interaction where there's a choice to, in your words, be empathetic or to demonstrate strength, in our words, we talk about warmth and competence. You have to take a step back and understand the context, as you mentioned earlier. Context really is important. And you also have to hold people accountable, but make resources and opportunities available to them.

[00:14:32] Rob Siegel: I think it's a false choice for us to have to choose between being ambitious and being kind. I think that's just fundamentally a false choice. You know, one of the things I saw in the book, there's fifteen or sixteen leaders that we write about, all of whom are successful by any figure of merit. They run decent sized companies. Their companies have done well. They've achieved a level of success. Not all large companies, some are startups or mid-size companies, but they're all very human. You can look at these people and say, these are good people. They may not be the people we read about all the time on social media or in the mainstream media, but they're there. And so I want readers and my students in the class to be able to look up at these people and say, I can choose to be like that if I want to. I can be a leader who is both ambitious, but also a good human. And these people are out there. They just don't seem to be shown off very often in what we see when we read articles or we watch videos or whatever the case may be.

[00:15:26] Matt Abrahams: I'm glad you're shining light on people like that and helping us learn from them. I'd like you to get meta for a moment. And what best practices do you use to help you gain and maintain students' engagement and attention, because you really are a master at it.

[00:15:40] Rob Siegel: I don't know about that, but thank you for saying so. I, when I go into a classroom, I want to make sure I know the material ten times better than the students do. Because they've got so much going on in their lives, it's generally easier for me 'cause I've been studying it and they've got so much happening. It's about preparation for me. I was taught to teach by Robert Burgelman. And when you have structure, for me, that allows me to think about what are the lessons I wanna get across and how much time will I spend on things. What happened with my teaching style, over time, was I found that my best classroom experiences were the unscripted.

[00:16:13] And so where I used to be very scripted, I got to the point of I have four or five key questions or topics, and then I just go in and see where the students take me. And what that allows me to do or forces me to do is to be very present. I have to listen to what they're saying and see where we're gonna go. And sometimes they'll take me places in areas that I didn't anticipate, and I try to maybe let that run. The key for me is also to be interactive. More so than most today, and I have to be a bit careful, especially doing it with Gen Z, is I would like to challenge their thoughts, and I'll say to them, if a student says X, I'm gonna say why?

[00:16:44] I'm not saying you're wrong, but tell me why? I will often explicitly stop the room and say, I'm not trying to make anybody look bad, but leadership today is all in the gray. Leadership today is very few of the easy decisions get made lower down in an organization. And so I want the students to think about what they say and then to defend their points of view and to highlight, look, if this were a, an executive meeting or we were in a conference room, you're gonna have really smart peers who are gonna look at it differently and I'm gonna challenge you. And so I want them to be able to get used to that. I want them to practice that, but I also want them to know that these issues are hard and these issues are increasingly difficult.

[00:17:20] And by the way, the classroom's a safe space to do that in. And I want them to know that they can take risks there. And so as long as I'm prepared, as long as I know the material and as long as I can be, hopefully tough, but not mean, you know, and then to also try to remember the dynamic of they, I see myself as basically them. I sat in those chairs thirty some odd years ago. But I look in the mirror and I don't look like them. I've gotta remember there's that dynamic. And sometimes that's hard for me to remember 'cause I know how smart they are, and I think I'm just debating somebody who's just as smart as I am, if not smarter, but I know that they might be looking at that differently. So I think it's that awareness of the context, being ready. And then I was trying to also have some fun, like I love what I do. 

[00:17:57] Matt Abrahams: And you do it very well, and you do it not just in your classroom, but in your interpersonal communication too. I think this notion of setting up a safe space, making sure that you're prepared, but not so prepared that you can't be spontaneous and present, and preparation allows for that spontaneity, I would argue. And being a little challenging, but also being open to having some fun and seeing where things take it. Those are really essential skills that, through time, people can develop. 

[00:18:23] Rob Siegel: I also, I think about some of the walks you and I will do, and we start almost always, how's the family? How are our spouses, how are our children doing? You can't be perfunctory about that. Like you actually have to, I think, care about the other person and the other person can tell. And so I think if you have that genuine interest in learning about other people and knowing what's going on, I think that also helps build a connection on communication. 

[00:18:44] Matt Abrahams: And that leads to trust, absolutely. And, and it's really critical. Well, you know the drill. You've been here before. Before we end, I like to ask three questions. One I create just for you, and the other two are similar to everybody I interview. Are, are you ready?

[00:18:55] Rob Siegel: Yep.

[00:18:56] Matt Abrahams: So you have been honored, more than once, to give what's called a Last Lecture. It is the students here at, at the GSB at Stanford select speakers to come in. You have been honored many times with this. And you've shared with me that at the topic of this year's last lecture is going to be about education. For those of us listening who won't be in that auditorium when you give that lecture, can you give us a distilled version of what you intend to say and why education is so important at this moment? 

[00:19:22] Rob Siegel: I'll do that in reverse order. I think education is important to me personally, having devoted twenty-two plus years of my life being a teacher, and so it's something I care very passionately about. The reason I want to talk to the students about that this year is I have a strong belief, as we've talked about actually in the systems leadership class, I think education is the great equalizer for society. It allows us as humans to do better for ourselves and for our families and our communities, and the role and importance of education. And so the students I'll be talking to, that's kind of the tie that binds, if there is no education, there's no reason we would be there together. And even the place to come into Stanford, like it's not about, you know, our students work on startups and they work on the soft skills, and we try to teach them about communication and empathy and finance and marketing and all that stuff.

[00:20:08] But so much more that holds us all together is education. And my wish for them is that in whatever capacity they choose to do it, whether it's in their local PTA, whether it's in their community, whether it's trying to help people in other parts of the world get better educated, or even if they wanna help the alma mater to spend some of their time on education. It's really the foundation by which all of us get to do what we do. The expression is, it's the big X in our equation. And I want them to hopefully spend some time or some number of them committing to not just seeking a business career, not just seeking all the benefits that come from a successful business career, but that notion of thinking about others and education is just one way of doing that.

[00:20:49] Matt Abrahams: Absolutely. Amen to that. Education is critical and it's what really can make a difference in people's lives. Who is a communicator that you admire, and why? 

[00:20:58] Rob Siegel: Irv Grousbeck, our colleague. Irv has just a grace and a dignity with how he carries himself that I just find so admirable. He's who I go to when I'm wrestling with heart issues.

[00:21:08] Matt Abrahams: Irv is amazing in his Yoda, Zen like master a way of helping you see things differently. You've picked a good role model there. What are the first three ingredients that go into a successful communication recipe? 

[00:21:21] Rob Siegel: Understanding the key things you're trying to get across and being very concise about that. Secondly, knowing where your audience is, whether that's one-on-one, whether it's in a small group or in a large audience, where are they at that moment in time? And then third, for me, extensive preparation. So for this last lecture that I'll give next week, it's a new speech. I'll say it out loud, probably twenty times in my home office. And the hope is that when I'm in front of the students, they'll think that it's just flowing out, but it's not. It's something I will have practiced just to make sure that I get the key transitions, the key messages, and hopefully deliver it with warmth and kindness, but not shy away from hard issues. 

[00:22:01] Matt Abrahams: So it's about focus, it's about context, and it's about preparation. And those three ingredients make up an effective recipe for sure. Rob, I knew this was gonna be fun. It always is fun when we get together. I greatly appreciate you bringing your insights and wisdom to the show and to putting them out there in all the ways you do, but especially in your new book, The Systems Leader. Thank you and best of luck.

[00:22:22] Rob Siegel: Thanks Matt.

[00:22:25] Matt Abrahams: Thank you for joining us for another episode of Think Fast Talk Smart, the podcast. To learn more about leadership, please listen to episode 37 with Rob Siegel and episode 35 with Jeff Immelt. This episode was produced by Katherine Reed, Ryan Campos, and me Matt Abrahams. Our music is from Floyd Wonder. With thanks to Podium Podcast Company. Please be sure to follow us on YouTube and LinkedIn. And check out FasterSmarter.io for deep dive videos, English language learning content and our newsletter. Please consider our premium offering for extended Deep Thinks episodes, Ask Matt Anythings, and much more, at FasterSmarter.io/premium.

Robert Siegel Profile Photo

Robert Siegel

Lecturer at Stanford University, Venture Investor, Author