266. When Innovation Requires Disappointment: AI Strategies and Leadership – With Kate O’Neill

When Innovation Requires Disappointment: AI Strategies and Leadership – With Kate O’Neill

About this Episode

Ep. 266 – Does this sound familiar? You’re in a leadership meeting and someone asks, “What’s our AI strategy?” or “How should we be using ChatGPT?”

If you’ve been in one of these conversations lately, you’ve probably felt the pressure to have an answer. But here’s the thing, you might be asking the wrong question entirely.

This week, we’re diving into insights from tech humanist Kate O’Neill on why chasing technology trends is letting the tail wag the dog, and what successful leaders do instead.

The core insight? You don’t need an “AI strategy.” You need to understand how AI helps you achieve the strategic objectives you’ve already identified.

✅ You’ll learn why starting with purpose (not technology) transforms decision-making

✅ We’ll explore the Disney example that makes organizational alignment crystal clear

✅ We’ll share how to have productive AI conversations at three different levels

Kate shares real insights from her work with companies like Netflix, Google, and the United Nations, plus simple ways managers and teams can rethink how they approach change, technology, and decision-making.

If you’re tired of scattered (AI) initiatives that don’t seem to connect to anything meaningful, then this episode will help you have a clear strategy and a team that’s aligned.

Listen now on our Spotify, Apple Podcasts, or YouTube.

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Episode 266 Transcript:

Ramona Shaw: [00:00:00] Welcome to this episode of The Manager Track podcast. Today I have a very special guest with me, and I know you’re gonna love this episode. We’re gonna talk about s disappointment as a key to innovation and future ready leadership.

The guest that I bring on is Kate O’Neill. She’s a wildly recognized tech humanist, a prominent author, a keynote speaker, and a strategic advisor focusing on the intersection of technology and human experience.

She’s also the founder and CEO of KO Insight. Affirm, helping organizations make technology decisions that prioritize human wellbeing and ethical considerations.

But let me get a little bit into Kate’s history. Kate was among the first 100 employees at Netflix where she established the company’s first content management role. She also developed Ishiba America’s inaugural Internet and founded Meta Marketer and Early Digital Strategy [00:01:00] and Analytics agency.

Her client portfolio includes industry leaders such as Google IBM, Adobe, and institutions like Yale University and the United Nations. It’s quite a list than an impressive resume

then in 2020, she’s been shortlisted for the Thinkers 50 Digital Thinking Award and has participated in panels at the Thinkers 50 Award Gala. Discussing topics like AI’s impact on human work and experience.

Now she’s also the author of several influential books, including Tech Humanist, a Future So Bright, and Her Latest, what Matters Next released in 2025.

I am really excited to share this interview with you. I know you’re gonna take a lot away from it, so without further ado, let’s dive right into the conversation with Kate.

Here are the two questions. This podcast answers. One, how do you successfully transition into your first official leadership role? And two, how do you keep climbing that leadership ladder and continuously get promoted, 

although [00:02:00] the competition and the expectations get bigger. This show with The Manager Track podcast will provide the answers. I’m your host, Ramona Shaw. 

I’m on a mission to create workplaces where work is seen as a source of contribution, connection and personal fulfillment. And this transition starts with developing a new generation of leaders who know how to lead. So everyone wins and gross. In the show, you’ll learn how to think, communicate and act as a confident and competent leader. 

You know, you can be.

Kate, thank you for being on The Manager Track podcast. It’s really great to have you here. Thank you Ramona. Glad to be here. I. I already introduced you to the audience, but I’d love to hear from you when you think about your career starting off or early on being in, in Netflix content strategist and setting up that apartment, and now to the work that you do today with really leading the conversation around AI and the human-centric approach to ai.

What is it for you? What is that red thread that you, in reflection, look [00:03:00] back and you say like, oh, okay, this was what guided me from there to here? You know, it’s really funny. In order to find that red thread, I have to go back one step farther than Netflix to the fact that I was a language major, I was a linguist in my education.

And so I, I’ve always been really interested in learning languages and in the. In the core of language, like why do we use language? What is language for? What are we trying to accomplish through the means of language? And I think that that has been this kind of constant for me throughout my career and throughout my life, and you can find it throughout my career, you know, this kind of constant question of how do we connect with one another?

How do we communicate with one another? How are we using technology and tools to better connect and communicate with one another? And I think even as you think about the, the manager questions throughout my career and throughout, you know, the work that I do now and, and [00:04:00] helping leaders make better decisions around technology, it still has a lot to do with how we communicate with one another.

You know, what are we trying to communicate? What’s meaningful? What are we actually prioritizing? So it’s interesting how I feel like. Everyone gets to find the way that they see the world, right? Like the lens they see the world through. And for me, the lens I see the world through is always language Ramona, I wanna ask you, what is your red thread? What is your, your lens that you look at the world through? I definitely have this intersection between business results and building and on the other side that like deep human interest. And it’s funny, I was, as I was deciding my master’s degree back in the day, I signed up for human resources first and then like pull back out like a week into the semester first semester.

And shifted into finance, but I can even go back then looking at, and it was constantly in my head of like, how do I connect the business [00:05:00] business results with like that human aspect and human behavior that I was always super interested in, even as a young child, like wanting to know how people live and why they decide what they do.

And, and just like that always fascinated me. And you know, now I, now I get this to be my job where I am listening to people tell their life stories or their own internal reflections. Yeah. So you can almost take an anthropologist view of the whole thing. Right. And all in the business context.

Yeah. Yeah. And every single job sort of ties into that. Thank you for asking the question. Now let’s talk about today. I think you are at the forefront of conversations that need to happen. What is it specifically for you that motivates you and gets you up in the morning, the thing that you wanna push forward?

Yeah. And so I, I think it’s interesting that we started out with that, that red thread and that lens conversation because so much of the way that I see the problems that I’m trying to solve in the world and the, the clarity I’m trying to offer [00:06:00] have to do with, with meaning and, and the shape that meaning takes in business is purpose.

You know, and I think we, we talk a lot about purpose in, in management work and leadership work and purpose. I think often. Starts to sound a little bit like this very vague, esoteric idea that’s sort of touchy feely and soft and fuzzy all at the same time. But it, but everyone says it’s so important.

It’s so important and, and I think the reason why, for me. That it’s so important and that what makes it seem a little more graspable to people is when you really come at that question of what lens are you looking at the world through and how are you understanding what matters to people? How are you understanding, you know, what matters in the business that you’re running and what matters to the people outside of your business?

What connects those and how can you make that clearer? How can you make it stronger? How can you use technology, for example, to amplify and [00:07:00] accelerate the value that you’re adding through that connection of what matters to you and what matters to people outside of your business? That’s what purpose really is, in my view, is that that clarity of your meaning and mm-hmm.

And other people’s meaning what they’re trying to accomplish. So I, I feel like. For me, what drives me, what makes me really excited is the idea or the, the opportunity to bring some of that clarity to people in the work that I do and help them see the clarity of the value they’re offering and of the, the good that they can do in the world, even as they build very successful businesses and, and bring their work to scale.

Can you break this down into an example or just demonstrate that in an example? Either for a company or, or for a department or an individual team. ’cause many of the listeners will not own, some are running companies, but some of them are just running teams. And so [00:08:00] there is sometimes a disconnect of like, how much agency do I actually have if I’m just one section of the, of the business.

So I’m curious to hear, based on your experience working with leaders. What that could look like specifically. I have one, one favorite example is to think about and it’s ’cause it’s an easy one for many people to visualize is Disney theme parks because the way that you can describe in, in very simple language and the way they do describe what their purpose is.

Their strategic organizational purpose is create magical experiences. And I think that’s a really crystal clear one because when you think about everyone who’s in any role across the organization, whether you are. Working in a souvenir shop on Main Street, in a theme park, or whether you are answering phones in a call center, trying to help people connect to their vacation and plan all the details, or you’re sweeping streets.

I mean, it doesn’t matter. If your job is to contribute how you contribute to [00:09:00] creating magical experiences, then that crystallizes things for you. That shows you what you have. The autonomy and the agency to do, assuming that that management, that leadership has done the right thing and made it clear that within the sphere of your influence, you should help contribute to creating magical experiences.

So I think that’s a, that’s one that’s really vivid for people and I think it helps to drive the point home. But then I think even on top of that, it becomes even clearer when you think about how technology layers onto that, because. They invested a good amount of money into those. My magic band wearables and the My Magic bands were all about connecting people to the data that they were going to connect through the park, you know, all their, their lodging information, their payment information, their bookings and reservations at various restaurants or, or rides or whatever, and all of this, the preferences they had, all of those things were.

Able to be stored [00:10:00] in those devices and it would open doors and open gates and magically connect them to their reservations and, and pay for things. And that does feel like a magical experience, even though it’s just technology. It feels like a magical experience. And yet the. Price tag for having done a huge transformation project like that is enormous.

But when you can think about how much ROI and how aligned it is with what the business purpose is, it becomes a lot, a lot easier at a leadership level to feel good about that in investment, to feel like we’re making the right investment because it, it aligns so clearly with what we’re trying to do.

So let’s assume we’re in a leadership meeting where we’re talking about making strategic decisions. What are you seeing as an observer? First mistakes that leadership makes, and then what are sort of the key messages that you wanna, you know, whisper, whisper into the room that they should hear to pay attention to?

[00:11:00] Yeah, I think the first thing that comes up an awful lot with my clients and the folks that I speak with in keynotes all the time is a, a real tendency that I think leaders have to chase the shiny object, right? And the shiny object very often is technology. Or it’s some new organizational structure or it’s, you know, some new methodology or or, or something.

But often these days it is technology and most often these days it is AI in some form or other. And so what you hear a lot are like, what I hear a lot in my work. Is what’s our AI strategy or what’s our, you know, automation strategy or what, fill in the blank here, right? But that is actually letting the tail wag the dog.

That is not how strategy work is done. Strategy work is done at that more holistic level. Thinking about purpose and origin stories and you [00:12:00] know, value creation and how it is that you’re connecting with the people outside of the organization and how you’re creating those experiences. Then technology is very, very useful and relevant in helping fulfill on that strategy.

So you might say, how does AI help us achieve the strategic objectives we have identified? I. But you don’t have an AI strategy per se. And I think that conversation, that distinction, you know, feels, I think to some people like nitpicking, but it makes a really big difference in the way leaders frame that question.

And it makes a very big difference in the prioritization and the way they approach, you know, kind of allocation of resources and alignment of resources. And it makes a difference in the way everyone in the organization sees their role in helping fulfill the success of the mission of the company too.

Even if they aren’t necessarily tied up in how we’re [00:13:00] rolling out this particular AI tool or something like that. If they understand the overall objective of the company and what that strategic organizational purpose is, and then they see, oh, okay, we’re doing this AI initiative and it’s gonna help us.

In the procurement side of the business, it’s gonna help us be hopefully 10 to 20% more efficient in our procurement. That sounds to somebody who works on the other side of the business, like it doesn’t affect them. But actually if you have helped communicate here, would come back to, you know, communicating clearly, right?

If you’ve helped communicate what it is you’re hoping to accomplish at that organizational level strategically by having this procurement system bring more efficiency into that side of the business, how it’s going to help the other sides of the business, how it’s going to help everyone be able to, be more effective in, in what they use and what they report and things like that.

However you communicate that it’s going to help people understand how they are a part of initiatives that sound totally [00:14:00] removed from where they are. I think another, another fun example of this that, that might be useful to share is that when I was at Netflix in those early days, it was the, I was one of the first a hundred employees of Netflix.

So, you know, we, we didn’t have a, a huge enterprise organization, like many of your listeners may be part of. So it wasn’t that difficult to stay abreast of things that were going on, but it was still important as a growing organization, a fast-growing organization to understand how my work connected to someone else’s work and how theirs connected to someone else’s.

And so what we did, what that I think is such a important lesson for much larger organizations that even the smaller company was doing is to say, we have a central. Goal that we’re trying to achieve. And at that time it was we wanted to grow to a million customers, I believe was the number. And then everyone had in their own department and their own group, their own metric that would contribute to the success of that top line [00:15:00] goal.

And so you can almost draw an organizational chart, not of the teams and resources, but of the KPIs, of the metrics that we were using to contribute. To that top, that most important objective. And so everybody could feel, you know, well, of course I want you to succeed in this metric that you are measuring, because I can see how that contributes to the top level measurement.

I’m contributing to it a completely different way. I’m coming at it from a different direction. But I wanna help you and support you in how you are getting to that objective. And it really, really helps cut across the organization in ad hoc teams and in the ability to collaborate in organic ways that are authentic, because we all want the same things.

So what I’m hearing from you is there’s either a tendency where we’re looking at the different AI transformations and initiatives, and then when we communicate them in a bit of a siloed approach mm-hmm.

It can quickly get scattered and it can turn [00:16:00] into a disconnect from what the purpose is and what we’re actually trying to achieve. Mm-hmm. Especially for people on the receiving end who don’t have the big picture. Right. Who then feels sort of like pulled into different directions. Or we can constantly start with the top.

Main purpose and then communicate from here on out of how everything else supports that main purpose or the main KPI in that case. Now, when I think about a range of organizations, let’s say that I’m supporting, there are some where. Let’s say a company that mainly does translation services, they know they’re gonna completely be disrupted.

Yeah. It isn’t a question like everything that they do maybe even the whole purpose needs to completely be rethought. But then there are companies that are not gonna be disrupted. Let’s say this is an organization that does something. Brick and mortar, a hotel, a restaurant, and yes, sort of the automation, the technology behind the scenes can help, but they’re not it’s hospital.

They’re gonna do what they always did. Then there’s this huge range in the middle mm-hmm. Of [00:17:00] organizations who don’t know yet will they be disrupted or in which way. And I wonder sometimes how much leaders think AI is there to change the direction of the organization at large. And that seems exciting, especially for visionaries.

And people who like new ideas versus it just being a supporting function to the purpose that’s already been defined. And I think it’s a really meaningful observation and question, I think kind of rolled into one. I I think what happens with AI is, as you know, I’m sure, and I’m sure many of your listeners know, AI is a very broad term for a wide range of technologies.

It’s a, an umbrella term that encompasses. Many different kinds of things from all the way from, you know, the, the tools that make recommendations on, you know, Amazon when you buy something to suggest to you what else you might like to buy. To facial recognition, to, you know [00:18:00] sensors that recognize when you are approaching to, obviously chat, GPT and the, the category of large language models and lots and lots and lots of things more so when we talk about ai, we are really talking about a very diverse set of functions and skills.

So when I think about what you’re asking there, or what you’re saying too. I think it’s really important to acknowledge your implied understanding is correct. There are different levels of where this is relevant within the organization. It, it’s going to matter in. In an organization as a whole, a leader who’s leading a CEO or, you know, the boards of directors and things like that are going to want to think holistically about how AI is disrupting the category that they’re in, the industry that they’re in, and, and how it’s going to change the entire operating model of the company.

But that’s just one layer I think underneath of that layer, you have to be thinking about. [00:19:00] The ways that the company breaks down into its organizational functions and how it does what it does. And how, what it sort of secret sauce is. And that is obviously likely to be disrupted in various ways by different kinds of, of technologies, including different kinds of AI as well.

And I think even at when you take it to the individual level mm-hmm. You start thinking about how is AI part of how I do my job, how I’m going to augment my job, how my job is going to be changing over time and like what tasks. Are going to be automated that I used to do, and it used to be really important that I do, but now it’s not that important that I do that task anymore.

I think that’s part of what is so complicated about the future of work as a conversational topic, that we often conflate the future of work with the future of jobs and the future of. Industries and the [00:20:00] future of workplaces and so on, you get the idea. Like there’s a lot of different concepts that can be disambiguated and talked about separately, but often we think about them, we talk about them as if they’re the same thing.

And so I think it really helps for listeners thinking about this within their organizations and having this conversation. Within their organizations, really push yourself and your colleagues to, to break that down a little further and make sure you’re talking about the same level of disruption are you talking about as, as an organization, are you talking about individually?

Mm-hmm. And are you talking about like what category of technology are we really anticipating might challenge us as an industry? Because certainly there are still going to be ways for a translation agency, for example. To offer a kind of value that is unique to the moment, right? To be able to offer accuracy and human [00:21:00] nuance and, you know, cultural sensitivity and context sensitivity and all the things that we know that translation, automated translation isn’t necessarily all that good at yet.

And we would want to rely on human translators for the kinds of things that are going to be extra sensitive when it’s healthcare related, government related. Like anything where there’s a, a very, very critical context for getting it right and getting the nuance right, and you could extend that across to different types of organizations, different types of industries, just the same.

I think everybody has their own. Questions and considerations of where they bring a unique value. Mm-hmm. That so far, AI has not pushed aside, and they need to think about that at every level of the organization. What I’m taking from this in the aspect of what can leaders do with this?

I’m hearing you say, let’s say if a leader says, I have an offsite, we wanna talk about ai. We’re gonna spend two, three hours with the team, 15 [00:22:00] people in the room talking about. AI and impact on us as a team. In that conversation, I’m hearing you say is a get really clear on what level are you talking about?

Mm-hmm. Like what’s the level of AI influence? Are you talking about sort of broader, what the team does and the team’s purpose, or is the purpose very clear? Then start with that. Talk about the main purpose, the main KPIs, and then look at the workflows and the tasks. The tools that the technology currently in use to look at where, how to optimize it to then get to that outcome, the KPI or hire a KPI.

Yeah. ’cause I think there’s, every, every leader, every manager, every professional right now wants to know how they should be using ai. And they’re, they’re figuring out day by day how to use. AI and other technologies to advance their own productivity and effectiveness and, sort of shore up their own value contribution into the organization and into the industry.

That’s just clear [00:23:00] across the board. I have consultative sessions on a regular basis with clients whose executive teams want guidance on how they can better use AI tools for their own effectiveness and their own. Sort of leadership communications and things like that. Mm-hmm. That’s cool. That’s fine.

But that’s not the same as considering how do we as an organization think ahead, you know, a few years, 10 years, 20 years, how do we think about what the, the next likely steps in our industry are likely to be, as well as adjacent to our industry? What are some of the intersecting pressures and opportunities where you might see movement on that sector that’s adjacent to where we are.

And maybe there’s opportunity for us to distinguish ourselves. As an agency that understands that sector or we’re, you know, we pick up a little slack or we step away from that sector and we move over here. Those kinds of considerations that, that future readiness is incredibly important for leaders to think about and to talk about and to plan.

[00:24:00] That’s work that I do with my clients. But I think it’s a conversation that leaders can have amongst themselves very effectively too. I think it just requires that, that they understand that they’re asking. Questions at different levels of abstractions, different levels of time period, right? Like, so are we talking about what we are, what we’re doing now, what we’re gonna decide today about this?

Or are we talking about what we think we’d like to set ourselves up to decide over the coming 12 months to 18 months? Mm-hmm. And then kind of longer term. You know, where we see making trial investments into how we might bring more automation into, these procurement workflows or into our customer support function or that sort of thing.

But, but what I don’t wanna see, what I, too often see is managers and leaders jumping the gun and saying, great, we’ve got chat, GPT, we can get rid of our customer support function now. Right. That is. Or, you know, whole [00:25:00] newsrooms being replaced by chat GPT and that’s it’s way too rash.

And you see a lot of these decisions where the leaders backpedal on them shortly thereafter. Right. You, you see this happen again and again. So I think it, what we do is we take a, a much more both and kind of approach to it. We wanna have a foot in that water. We definitely want to, you know, be sticking our toe in and figuring out.

What makes sense for us, where the value is, how we want to build, you know, what, what direction we wanna go. And we wanna be sure we’re being clear and communicative with our teams about how we value them, how we value their contribution to the team, and how we want them to help us figure out the future with us.

And that, that sets up a, an environment where people aren’t scared that they’re going to be replaced by. Technology. Mm-hmm. They’re more curious about, huh? Yeah. You pre, you present an interesting challenge because if our value is this and what we’re trying to do is that, then [00:26:00] AI could really help us do more of this with more of a the team involved.

And so it becomes much more of a, a group problem solving exercise. And I can imagine that also supports the upskilling, reskilling and, and sort of people’s adaptability due to change. Yeah. When you have these type of conversations, absolutely. People become curious about how, what skills they can add to their own re repertoire as opposed to, having a defensive posture and going like, mine, all mine.

Like, I don’t wanna let go of any of these responsibilities and let AI take that over. Even for tasks that AI is perfectly capable of taking over at this point in time. Oh, that, that could, is, could get us down into a whole other conversation. Very interesting one, because I know how much the ego plays into what we do or don’t do.

And I’m sure there’s some you know, understandable concerns over people’s. Safety around their job that influenced those decisions as well. [00:27:00] But I’d like to talk a little bit more about the point that you make around strategic disappointment. Mm-hmm. Tell us what you mean by that.

Yeah, so it’s funny, I, so I just wrote an article for a fast company about strategic disappointment. And it’s a, it’s a funny term. I think people come at it like a little bit sideways, like, what, how, what are you talking about? But I think of it partly in contrast to this other term that I use in my work, which is strategic optimism.

Mm-hmm. And strategic optimism. I’ll start with that first because I think it’s really important to recognize that strategic optimism is a way of thinking about. The future that is neither perfectly optimistic nor perfectly pessimistic. It’s not just about dystopia versus utopia. It’s a way of saying, look, we know that there are risks and harms with whatever we’re looking at, whatever decision we’re looking at.

Like rolling out AI in a, in a customer support function, for example. And we also know that there are opportunities. So how do we lean into the opportunities while [00:28:00] mitigating the harms? How do we embrace the best possible futures that we want to create and create some safety and security around what the risks are?

And similarly, what I think strategic disappointment is the opportunity to say in order to do new things, in order to bring about new things into the world. People who are not going to be excited about that change, who are, who are thinking, I liked it the way it was, are going to be disappointed. And you need to get into the habit of questioning whether the change that you’re bringing about is truly in line with that top level strategy that we’ve talked about multiple times throughout this discussion.

And if it is. Then you have to believe in it enough to be able to disappoint people. Mm-hmm. And I offer a grid in, in the fast company article. People can find it on fast company.com. Looking up strategic disappointment. And I offer a matrix, a two by two matrix [00:29:00] that breaks down the way that you can think about.

Certainty versus disappointment in the decisions that you’re considering. Like if you have a, a decision that you need to make and the certainty is high and the disappointment is low, well by all means, you know, lean into that, do that mm-hmm. Enthusiastically, just know that that is not likely to bring a whole lot of innovation with it.

Mm-hmm. On the other hand, if you have a change that you think needs to be made and your certainty is fairly low, but your, your disappointment is fairly high, a lot of times what those are, are situations where you think there’s a transformative potential, some kind of true innovation potential, somewhere you can pivot the company into a, a whole new area.

But you have to do it very carefully and you have to make sure that you’re messaging that within the company carefully too, so that people don’t begin to think that you are chasing something that is totally I irrelevant to what they’ve understood the mission [00:30:00] of the company to be. So you have to make sure that people can see the trajectory that you see, the opportunity you see.

And there’s different, so there’s different communication challenges for each of these scenarios. But there are examples that I share as well, like Apple deciding to get rid of headphone jacks, and that was something that tech journalists and the general public were very critical of at the time.

People called it they were, they called it user hostile. They said it was stupid. And now, you know, we’ve got these and no one can even remember. People are so com comfortable with, you know, AirPods and Bluetooth headsets that you see people with headphones every so often, but it’s just not, or you know, the wired headphones.

It’s sort of a. A Gen Z trend, I guess. But you also also recognize that most people can say like, oh, that turned out to be a pretty good decision, right? Mm-hmm. So [00:31:00] it’s the confidence of recognizing why you’re making that decision, what it ultimately is leading you to, and the the future that you’re freeing up in that strategic optimism sort of way.

The future, you’re freeing up in order to pursue it. And if you have that clarity of the vision, you can withstand the disappointment that you’re creating, but you just have to make sure that you’re creating that disappointment intentionally and purposefully, and not in a way that’s hostile or harmful to people.

I. Because that means that you haven’t communicated it clearly enough. You haven’t shown what the, the vision that you have for the future is, you know, you’re not casting a clear enough vision. Oftentimes, that’s where leaders fall down, is that they will talk about the benefit of making this change now, but they won’t cast a clear enough vision about where we’re trying to go as a result of making this change.

As you’re talking about this, it’s becoming like really clear to me that when you talk about strategic disappointment, and I see this in my own decisions [00:32:00] too, really taking the disappointment factor into consideration almost as if that was part of the strategy. So that I don’t see it as, oh, it’s, a negative side effect or byproduct.

Of it, but I, if I put that into the matrix that you just explained, I then can actually see what kind of transformation we’re gonna go about based on the enemies I create or the disappointment that will ensue. Yeah. It all connects to, in my book, which I know we briefly talked about yep.

What matters next there, one of the, the models that I, I introduced is called the now Next continuum. And along that continuum, you know, this is a way of visualizing the timeline of past, to present, to future in ways that hopefully offer. A sense of it being less daunting to think about the future because people I think, often feel like the future is too uncertain for the, [00:33:00] the rapid acceleration with which we’re moving toward it.

It feels like things are changing so fast and we are going toward what feels very uncertain. But there are actually ways that we can put our arms around it much more and, and get some clarity about what we’re dealing with. And so these are some of the models that I lay out in the book. One of them is the, the clarity that, to your point.

We often talk about digital transformation or just transformation and innovation as if those are interchangeable terms, but they are not. They’re actually in two different places on the now, next continuum. The transformation happens in a, in the sense of bringing the past to the present. It’s catching up to the current moment.

It’s catching up. To customer expectations or to where the market has moved, what your competitors are doing and that sort of thing. All that, that’s all where transformation efforts focus. Innovation, on the other hand, is present to future. It’s saying here we stand. We’re looking ahead. We’re [00:34:00] trying to think about what green space we could create, what green fields we could open that nobody’s in, that we could totally do something new and revolutionary and create a whole new opportunity.

And at, at any given time, companies should be heavily invested in both of those activities because every company needs to catch up on something and every company should be looking ahead on something else. And that’s the balance that I think what we see here is that, that as you so astutely observe that disappointment is part of the strategy because it is trying to figure out, you know, what can we do to catch up with the moment?

What can we do to get ahead of the moment? And how are we going to manage the change that we need to, to manage? How are we going to manage the behavioral resistance to change the, the messaging of this to the public, the bringing the team along, making sure that they’re on board with the changes that we need to make.

And that’s all part of the human centricity [00:35:00] of managing through transformation and innovation. And that’s why that’s such an important part of using these tools like strategic optimism and strategic disappointment. Hmm. When you think about the next three to five years so this is a bit of a question to, to wrap us up.

What would you like to see, what would make the next three to five years really successful not just for you and your own work, but as you observe the evolution and the developments that you see in the market? Ugh. What a great question. It’s such a, a wonderful opportunity to think big and broad, and I, I love doing that.

I think for me, I loved that. You know, we, we started out talking about, I, I talked about how language is such an important part of my lens and my thinking, and obviously once chat, GPT came on the market in November, 2022 with as a large language model and all the tools that came alongside it. Everybody started to understand, [00:36:00] oh yeah, language.

That’s a really important way to interact with technology. But I think we have missed one really important detail, which is it isn’t just language as a tool itself, it’s the meaning that we wrap up in language that’s really important. And meaning actually takes other forms too in, in terms of the intentionality of the design that we use when we’re creating experiences in terms of the context we allow to be part of the decisions that we make.

If we’re creating. Patient experiences, for example, in a hospital or healthcare setting, it’s really important that we’re thinking with empathy about how scared someone might be about how and how much pain they might be in, and that we can, we design experiences with compassion. I. For that kind of thing.

So what I think is that as we see models like AI models move from just this language interaction sort of paradigm to, to things that are going to be [00:37:00] more more multisensory, we’re going to see a lot more integration. We gesture which we’ve seen some of, but maybe not as much of as we’re, we’re likely to.

We’re going to see other senses come into play and we’re gonna see more ambient use of technologies like we see with, you know, smart speakers in homes and offices. But more of that and, and I think it’s really important that we use the opportunity to think in a meaningful way. About how to use these multisensory environments, how to create the next round of technology, the next round of business opportunities in ways that really do fulfill as much of that meaning potential.

I. For people as possible and really thinking about what as a company, what meaning you are trying to convey and what, what meaningful experiences you are trying to have with the people who do business with you, and how can you. Amplify that meaning how can you [00:38:00] really lean into creating more meaningful experiences, whether it’s with technology or with good old fashioned conversations mm-hmm.

Or whatever that might happen to look like. And so I hope that’s what we start to, to see is the opportunity to use the great. Advancement in sophistication of technologies to go to a very core place with what we’re doing and the design of experiences that we’re creating around meaning and really making the most of that Thank you for sharing that. I think with all the sort of noise that we see around all of this, when we look what already has been built and already, you know, died out. I think if that component of the meaning and the purpose and that human aspect isn’t considered, it’s unlikely to be sustainable, at least based on what we’ve seen over the last few years unfold that that trajectory I assume will continue that way.

So you, you said that, you articulated that so [00:39:00] well. Thank you for allowing us, for creating that space in this conversation to think a little bit bigger. Beyond just the, how can I make my work more efficient and more effective, or how can I help my team try to figure things out? But really having that top down approach.

Yeah. And really anchoring it around that meaning. Well, thank you for allowing that, that opening to happen. Thank you Kate, for being on The Manager Track podcast. We will link in the show notes both to your book as well as your website, obviously, and that fast company article that you mentioned earlier too, so people can read up a strategic disappointment.

Wonderful. Thank you Ramona.

Thank you Kate. 

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REFLECTION & DISCUSSION QUESTIONS

  1. What’s a recent change I made that might’ve caused quiet disappointment and was it worth it?
  2. Where am I chasing a trend, instead of following our bigger purpose?
  3. What message does my team need to hear about the ‘why’ behind a tough decision?

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