In this episode, we dive into how complexity creeps into our systems—whether in software, organizations, or personal leadership. We start by looking at the evolution of Microsoft Word as a case study of feature creep and unintended consequences, asking why more options can end up stifling creativity.

We’re joined by Robert Siegel, Stanford lecturer and author of The Systems Leader, who unpacks why today is a uniquely chaotic time for leaders. He explores the cross-pressures leaders face—from balancing execution with innovation, to combining strength with empathy—and what it takes to thrive in turbulent environments.

Later, we revisit a powerful 2017 conversation with Seth Godin, bestselling author and entrepreneur. Seth reframes uncertainty as an inherent feature of modern systems, not a personal failure. He shares his perspective on adapting to continual change, why embracing smaller markets and iterative progress makes us more resilient, and how redefining success helps us stay in the game.

Whether you’re leading a team, navigating constant change, or just trying to keep your work meaningful, this episode will give you fresh strategies for thinking and acting systemically.

Five Key Learnings:

1. Complexity Creep Is Real: As with Microsoft Word, adding features to solve edge cases often leads to more user frustration and less creative freedom. Simplicity can be a competitive advantage.
2. Systems Leadership Is Essential: Leaders must operate with a systems mindset, recognizing the interconnectedness inside and outside their organizations rather than staying siloed.
3. Balancing Dualities: Success today means navigating cross-pressures, such as execution vs. innovation and strength vs. empathy—not just picking one.
4. Embrace Uncertainty: Uncertainty isn’t going away; learning to see it as a product of changing systems makes it less personal and more navigable.
5. Iterate and Focus Small: Applying your creative efforts to the smallest viable audience allows for better learning, less risk, and greater long-term impact.

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When Microsoft first introduced word in the 1980s, it was a relatively straightforward word processor. Its core value was that it allowed people to write and format documents digitally, which was a huge improvement over typewriters and early software like WordStar. It was innovative, it was relatively lean, and it was targeted at writers, students, and business professionals who just needed to produce clean documents. But as the software gained popularity, Microsoft faced increasing pressure from two sides. First, competing software like WordPerfect, which had niche features that loyal users loved. And second, from enterprise customers who demanded more and more capabilities tailored to their unique needs, like templates, macros, style guides, collaboration tools, and integrations with other software. So Microsoft did what most companies do. It added features, lots of them, and then more, and then even more.

Every release included new toolbars, sidebars, layout engines, auto correction tools, publishing features, collaboration options, and compatibility modes. At one point, Word contained so many features that Microsoft itself reportedly had a hard time documenting them all. In the early 2000s, a famous statistic circulated. 80% of users used only 20% of Word's features, but not the same 20%. In response, rather than simplifying, Microsoft introduced even more tools to help users find the features they needed. Tooltips, wizards, and ultimately that now infamous ribbon Interface in Office 2007. Each layer of fixing the complexity only made the system move more complex. The paradox.

Word was getting better by the metrics that Microsoft used. More powerful, more customizable. But it was becoming harder to use, more intimidating, more creatively stifling for everyday users. Writers in creative Pros began to feel overwhelmed. Writing a simple document now involved clicking through multiple menus, navigating styles, and sometimes fighting with formatting bugs from compatibility modes. Some creatives even began to flee Word altogether, seeking simpler distraction, free tools like Scrivener or Ulysses or Google Docs that embraced less as a feature. The story isn't just about software. This is about leadership, too.

As creative pros, as leaders, we are constantly building systems, processes, cultures, expectations, and whether we realize it or not, just like with Word, the systems we build can gradually become more complex as we try to fix problems on the fly, as we try to accomplish, accommodate every need, or just do what we're good at without stepping back to see the whole picture. It's easy to lean into what we're good at and in the process, make everything else more complicated. Because we're not thinking systemically, systems don't operate in isolation. Every action we take creates tension between priorities, across teams or within our own creative process. If we fail to think in systems and to account for the external forces that impact those systems. And we risk solving surface level issues while creating deeper dysfunction. The challenge is to slow down enough to see the system, to understand the crosswinds that we're navigating, the tensions that we're contributing to and the downstream effects of our well intentioned fixes. It means not just asking what needs to be done, but what does the system need in order to thrive.

Because the goal isn't, for example, just to add features, to solve problems or to do what we've always done. The goal is to build something coherent, something that works, something that lasts. On today's episode, we feature two conversations. First is Robert Siegel, author of the new book the Systems Leader. Then we're going to be joined via a 2017 conversation with Seth Godin about how creative pros and leaders can better approach the uncertainty in life and and work. This is Daily Creative. Since 2005, we've served up weekly ideas to help you be brave, focused and brilliant every day. My name is Todd Henry.

Welcome to the show.

Systems leadership is a way of thinking and a way of acting and behaving that allows today's leaders to deal with a world of increasingly complex, constant change and it seems like ongoing crisis.

That's Robert Siegel. He's a lecturer at the Stanford Graduate School of Business and the author of a new book called the Systems Leader.

And the idea is that leaders today need to live within a duality, operate at certain intersections and understand action and reaction inside of their organizations and between an organization and its entire ecosystem. I think that if we look at how leadership evolved over maybe the last three or four decades in companies in particular, people would often stay within their silos. That that silo be engineering, marketing, sales, manufacturing. And you came up and as you rose inside of an organization, you depended upon teammates who maybe they owned their functions. And then if all went well, you continued to rise up in an organization. And I think what's different now is we have to have a much broader understanding in a world where everything is connected, of what's going on inside of other organizations and even outside of our company. And there are a lot of cross pressures that are pulling leaders in opposite directions. Today we look at kind of these cross pressures that people are confronting and then we study certain leaders, all of whom are, I'll call them, really successful and also who have made mistakes and are flawed and try to understand what do they know, what do they not know and how do they get through these challenging times by really understanding action and reaction.

So you begin the book by stating that this is a uniquely challenging time to be a leader. We've both been around the business world for a long time, and so it seems like everybody is always saying, oh, this is an unprecedented time. But really, you make a really good case that this is really an unprecedented time. And you call it the perfect storm of chaotic forces. Why do you believe that this time we're not crying wolf this time? This is really a uniquely unprecedented time in the history of the world to be a leader.

I don't know that leadership has ever been easy, but if we look at what's happening right now, we see things like extreme technological disruption. Let's look at the rise of AI. I had a front row seat at the invention of the personal computer, the mobile phone, the Internet. The speed with which AI is impacting companies large and small all over the world is staggering. We see economic instability in all of the frameworks that we use post the Second World War about how countries were going to interact. That's changed. We see unprecedented geopolitical conflict rising up on a constant basis. We had the global financial crisis in 2007, and even when we saw SVB collapse a few years ago, and we see changing societal structures.

How are families constructed? How are societies constructed? The speed with which people cross borders. And this is just fundamentally different. And if we look at the last 25 years, we had the Internet meltdown, we had 9, 11, we had the global financial crisis, we had what I will call populism. 1. Oh, Brexit, yellow vest in France, Bolsonaro in Brazil, the first Trump administration, we had Covid. We have the current political dynamics that we feel here in 2025, this is the new Nor, and it feels like it's just constantly coming at us with increasing speed. If Alvin Toffler wrote in 1970 about future shock, this idea that technology was evolving so quickly and we have a hard time adjusting to it. That was 55 years ago.

And so I think this is an even harder time for leaders and individuals to make sense of the craziness that's going on all around us.

It does seem chaotic is a great word for it. It's definitely accelerated. The world feels more, maybe more random. I don't know if that's a good way to describe it, but it feels like there are more random inputs, more random forces coming at us that are almost unpredictable. Like, it seems like before you could generally see where things were trending, and now it's like, where did that come from out of the blue?

And what we see are leaders today. I call it unserious behaviors in a serious world. Things like we're replacing decorum with outrageousness. What gets them clicks or what gets them likes. We see them people focusing on trivial goals. We see people actually acting with disdain towards customers, indulging in self righteousness and failing to show spine when necessary. And we sit there and we look at this and we say, is this how leaders are supposed to be? And so we sit here and we feel like, oh, we've got all of these things coming at us at a constant basis. We turn on our computer in the morning, like what happened last night.

People seem to have no guideposts anymore for what does it take to lead an organization and to bring people along with you in these chaotic times?

I want to talk about the key dimensions or the cross pressures that you call out in the book. The first one is priorities. And you talk about the tension between execution and innovation. Could you share a little bit about what this duality or this cross pressure is?

We've seen a lot in organizational evolution and innovation, how companies need to, what's sometimes called the ambidextrous organization, exploit and explore. And the way that's happened in most companies is you had the people who made the trains run on time and then the crazy long hairs who did all of the crazy fun stuff. And I argue that in today's world, where technology is moving so quickly and as new inventions come in, we have to get it into production quickly. Individual leaders need to simultaneously be good at operational excellence and executing, but they also need to know how to manage small teams and innovation and figure out how to get that into operations very quickly. And I think what's different for leaders is they need to have both of those muscles that you can't just say, okay, I'm going to focus on one and my teammate will focus on the other, I need to know how to do both. Because of the speed with which invention is happening, I've got to quickly figure out how to commercialize things and if it works, get it to scale quickly. And so I think the difference is we as leaders used to be able to be good at only one of those things, and now we actually have to simultaneously know how to do both of those things. I think there's actually two things that people need to do.

The first is if we look at our career spanning, hopefully, if we're lucky, multiple decades, making sure that we do different jobs along the way so we get the understanding of different roles and different functions. And the second is a mindset, one which is am I delivering what I need to be on time and of high quality to people? And am I also trying and experimenting some new things? And by the way, even on something like that, it's. Are people doing stuff like understanding TikTok or realizing that's where the younger generation is getting their news? Are they bringing ChatGPT or Claude or perplexity into their everyday behaviors of how they write emails or create presentations or or create artwork? And so it's that willingness to make sure that we're doing both of these things that on the execution side that we keep our, what's called a say do ratio, keep that very high. We deliver on time and people can depend on us. But we also spend some times in our days and in our weeks thinking about I need to be growing my mind and learning new things and trying new things. And we used to be able to, if I focused on one or focused on the other, that was okay. But being able to be thinking about doing both, looking at our calendar at the end of the week and say, did I spend time on both of these things? And. And then also making sure, as I said longitudinally over our career, making sure we're building and growing our muscles by understanding different parts of our organizations.

Let's talk about people. The tension or the cross pressure between strength and empathy. Share a little bit about what you mean about that cross tension.

At the extremes, we've got the hard charging leader who might be a screamer or might just be demanding results and doesn't care why you couldn't get it done, just get it done. We've all worked for someone like that. And at the other extreme, I'll talk about somebody who's always talking about their feelings and that's great, but in today's world, we actually need to do both. And so some of the leaders we study really gave a great example of how to do both of these things. One of the ones we studied, and you'll see this kind of consistently throughout the book, was a lot of leaders who were hugely successful. But maybe we don't read about the media all the time. Kathy Mazzarella, who is the CEO of a company called Graybar, $11 billion in revenue, 10,000 employees. This, she's hugely successful.

She was described by somebody as an iron fist and a velvet glove. And she's one of these leaders, like when she walks into a room, we all sit up a little bit straighter. This is a very strong leader who deserves and commands our respect and our attention. But at the same time, she's very kind. She shows her humanity and she sees the humanity of the people in front of her. And I think it's being able to do those two things to say, look, if we make a promise to a customer, we deliver. If we make a promise to a teammate, we deliver. But also understanding that life happens and make sure that sometimes we see the whole person sitting in front of us.

I think there's a false choice between being ambitious and being kind. And someone like Kathy really does a good job of modeling that. But great systems leaders, they bring a gravitas of personality and purpose, intelligence and wisdom about the seriousness of the times. They're dependable when things are volatile. They drive change beyond self interest. And I think that the leaders that we studied in the book, the great thing about these leaders in the book, they're hugely successful by any figure of merit. And maybe we don't read about them all the time in the press, but they're out there, right? And they're there for us to see. And I think that that purpose, that sense of being able to be both ambitious and successful, but also being able to be thinking beyond the self, I think that's actually something that I noticed the world is hungry for.

And I believe that leaders today, in any size organization, have free will. They have a choice to be exactly who they want to be. And they can be bombastic and they can be obnoxious and they can be kind or they can be both. They can master these dualities that are required to get through these cross pressures. And so for me, that's what purpose is, that notion of ambition and statesmanship. Leaders can be actually both of those things. I think it's more about a mindset than it is even about talent. If people have the mindset, they can develop the muscles to figure out how to navigate through these things.

And I always say, start with the self, and then from that, then you can expand out for others.

Robert Siegel's new book is called the Systems Leader. It's available now wherever books are sold. And we only scratch the surface of our nearly 30 minute conversation in this episode. So if you want to listen to the full interview with Robert and hear about the other cross pressures that leaders are facing, you can do so@dailycreativeplus.com it's absolutely free. Just go to dailycreativeplus.com, enter your info and we'll send you a private feed where you can listen to all of our full interviews. One thing that all of the cross Pressures that Robert mentioned have in common is uncertainty. We are living in uncertain times. In a minute we're going to come back with a 2017 conversation I had with one of my favorite people, Seth Godin, about how we can deal with uncertainty in a more meaningful way.

Stick around, we'll be right back.

The expected way is to understand that certainty is something we do to feel safe. But we now live in a chaotic world where the safest thing to do is feel uncertain. But that's really hard to process and it doesn't always make conceptual sense.

That's Seth Godin, multi best selling author and entrepreneur from our 2017 conversation about uncertainty.

Let me riff a little bit on Russ Akoff here and talk about systems. Systems, when they are stable, create certainty. So that if you I'll use a bowling alley as an example. Go to the same bowling alley every week. You know where the counter is, you know how much it costs, you know who's going to be in your lane. It's safe, it's certain, and it's tempting to try to change our life to make more certainty. But in fact it's the systems around us that feel certain or uncertain. And what has happened in the last 20 years because of the massive disruption that a multi billion person connected world has created is we are now in this ever widening cycle of uncertainty because the system is changing now.

The system will get stable, it always does for a while. So if you think about email, for example, email goes years and years in a row as a stable thing. And then technology comes along and it changes again. So we need to learn to look at systems. So here's how I like to think about it. Back to the bowling alley. If you take the pins on a ten pin bowling alley and move them one inch closer to each other, you're going to get a strike every time. That in fact strikes are not about the pins, it's about the space in between the pins.

And once you realize that it's space that you're dealing with when you're bowling, it's a totally different sport. Well, the same thing is true in our lives that we do what we do and we make what we make, but we are part of a system. So Procter and Gamble had a system that was based on TV advertising. When the TV advertising system changed, everything changed, even if the formula for tide remains the same. So what we have to do when we're feeling unstable, when we're feeling uncertain, is look hard at the system that's causing us to feel that way and to Come to the conclusion that it might not be us that's the issue or the problem. It might be that the system has changed. And if you can learn to see the new system, then you can go back to doing your work.

Seth says one of the reasons that we feel this uncertainty so palpably, this tension that Robert Siegel was talking about, these tensions between the polar forces working against each other, is because as that space around us changes, as uncertainty increases, the space that we occupy can feel threatened. But Seth has some, I think, encouraging words for all of us.

The thing is, you probably should remind yourself that the only reason you have the position you have is because the system changed in a way that let you get in, right? That except for, you know, people who sweep chimneys or a certain kind of doctor, all the rest of us got our shot because the generation before us got left behind because the system changed. And you can't have it both ways, right? That you got your shot because there's chaos. So now that there's new chaos, it's hard to whine about it. The challenge then, is to figure out how to shoot your arrows without using them all up. And that means figuring out how to have an abundance of arrows, figuring out how to make it so that everything you do isn't the one and only shot you've got. Because if it's that filled with risk, well, then I'm not surprised you feel paralyzed. But it turns out we have more arrows than we think we do.

I've heard you say that before, that the goal is. The goal is not to win every time. The goal is to stay in the game. I think a lot hinges on how you define success for yourself or how you define the outcome that you're aiming for. And in some ways, I think that people, when they feel paralyzed, it's because they feel like, this is my one shot, this is my one opportunity. And they're not. They don't have that mindset of, you know, my goal here isn't to win big every time. My goal is simply to maintain enough that I'm able to stay in the game and place another bet.

That's right. But it's against everything we grew up being taught. That's not what they teach us about the sat, and it's not what they teach us about the soccer game, and it's not what they teach us about the job interview, and it's not what they teach us about our career or our investments. So why are we surprised, right? But in fact, it's that work in every creative field. And as you've pointed out so brilliantly, that's all of us. It's that work that makes it happen that every bestseller is a surprise bestseller, every hit movie is a surprise hit movie because the people who are supposed to know, can't know, don't know. They're always wrong. And yet we persist because the system is so complicated, we can't know for sure.

How do we prepare ourselves for that? What is it that we need to be doing to position ourselves to have more arrows or to be able to stay in the game when the environment around us is perpetually shifting?

Well, I think one place to start is by understanding that we succeed with the smallest possible market, not the biggest possible market. Another example of brainwashing that when we are trying to reach and engage with the smallest possible market, by possible I mean sustainable, that we can live with not one human, then the stakes are lower, but the feedback is better. We are not pushing ourselves to be average stuff or average people. We are pushing ourselves to engage in a meaningful way with a group of people that we can serve. And the beauty of this mindset is if you are wrong, well then there's another tiny group of people that may very well want to hear from you. And as soon as you get out of that monolithic, I only have one shot to make a first impression mindset, then you can go and do something worthwhile. So no one should try to debut their work on the TED stage because you only get one shot and it's going to reach a lot of people. You should debut your work on a TEDx stage in front of 100 people.

And if it doesn't go well, then go find another stage and try something else. If it does go well, Repeat that on 120 people and repeat and repeat and repeat. And the same thing's true. If you're a sketch artist or someone selling insurance, you don't seek to once and for all get the right answer. We seek to find the smallest natural group of people who are eager to hear from us and then deliver something that delights them.

Seth Godin's latest book is called this is Strategy. We actually had another conversation about that book, which you can find in the Daily Creative archives or at podcasts.todhenry.com no matter what we do, no matter what we create, no matter what kind of work we're involved in, we're not going to get rid of uncertainty. So in the face of uncertainty, systems become our friend. Understanding how to think about systems, how to live within the tension that uncertainty yields will make us better leaders, better creative professionals, and frankly, just better human beings. So here is to thinking in Systems. If you'd like to hear the full interview with Seth Godin and all of our full interviews, you can do so@dailycreativeplus.com just enter your name and email. We'll send you a private feed where you can listen to all of our bonus content. My name is Todd Henry.

If you'd like to know more about my speaking, my books, all of my work, you can find that@todhenry.com until next time. May you be brave, focused and brilliant. We'll see you then.