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Esther Derby draws on four decades of experience leading, observing, and living organizational change. She works with a broad array of organizations, from startups and Fortune 500 companies.
Esther started her career as a programmer. However, over the years she’s worn many hats, including business owner, internal consultant, manager, and team leader. From all these perspectives, one thing was clear: individual, team, and even organizational success depends greatly on the work environment and organizational dynamics. As a result, she’s spent the last 25 years helping companies shape their environment for optimum success. Her approach blends attention to humans and deep knowledge of complex adaptive systems. Esther has been called one of the most influential voices within the Agile communities when it comes to developing organizations, coaching teams, and transforming management.
Her formal education includes an MA in Organizational Leadership and a certificate in Human Systems Dynamics.
To hear more from Esther, check out her podcast, Change by Attraction, or read her most recent book, 7 Rules for Positive Productive Change: Micro Shifts, Macro Results.
Chatter: The Voice in Our Head, Why It Matters, and How to Harness It, by Ethan Kross.
Esther also enjoys reading medieval history. “History,” she says, “gives us a chance to look at the conditions [in our past] and what emerged from those conditions.”
Achieving product vision isn’t just about where we’re going, it’s also about where we begin the journey. A clear vision should also provide a path toward resolution of problems when they arise. Product teams should find their vision aspirational, yet relatable to their work and their values as humans.
In this episode of the Product Momentum Podcast, Esther Derby joins Sean and ITX Innovation Lead Roberta Oare to discuss the leadership principles she has discovered in her career. Simple, but often overlooked, these principles help product leaders navigate the environment in which we work: how we define vision, the interpersonal dynamics on and between teams, and how we apply these principles to achieve sustainable transformation.
Examining our environment is especially useful for product people, Esther adds. “Talk about how things emerge and what conditions are present that will allow for something to take hold and take off. How do we create the conditions that allow us to align deeply with our customers? What are the conditions that currently exist for them? How can we shift those conditions to allow our product to become an integral part of their lives?”
Catch our entire conversation to hear Esther explain why –
- Working on teams is messy.
- Traditional job descriptions are not as well defined as we think.
- Organizational structures and incentives get in the way of inter-team cooperation.
- Working toward your vision is like planting a forest.
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Sean [00:00:19] Hello and welcome to the Product Momentum Podcast. This is a podcast intended to entertain, educate, celebrate, and give a little back to the product leadership community.
Sean [00:00:32] Good morning, Roberta.
Roberta [00:00:33] Good morning, Sean.
Sean [00:00:35] I can’t wait to share this podcast with our audience. Esther Derby is such a rock star in the product leadership space.
Roberta [00:00:42] She has really brought some key points to my career to light and I just think that she’s got a brilliant, simple way of approaching success and change.
Sean [00:00:53] Yeah, well, buckle up. We’re going to talk about white space and the importance of inserting white space in the right places in terms of your team and in your thinking and in all sorts of areas. And we’re going to talk about her work, decades of work, in the product leadership space. I can’t wait to get after this, so buckle up. Here we go.
Sean [00:01:14] Well, hello and welcome to the Product Momentum Podcast. Today, we’re here to interview Esther Derby. She draws on four decades of experience leading and observing organizational change. She works with a broad, wide array of organizations. Her clients include all kinds of companies, from startups to Fortune 500 companies. She’s written such incredible books and has made such incredible contributions to the product community. I am forever grateful. Welcome to the podcast, Esther.
Esther [00:01:39] Thanks for having me.
Sean [00:01:41] So what’s got you excited about product development and product leadership these days?
Esther [00:01:46] Well, I’m really interested to see that people are starting to recognize that having diverse teams, on all sorts of dimensions of diversity, leads to better products. That’s what’s really exciting me lately, that people are starting to recognize that if you have a monoculture on your team, your product is going to be missing a lot of potential customers or ill-serving customers or potential users of your product.
Sean [00:02:14] I couldn’t agree more. I have a leadership framework that I usually open up our workshops with that talks about this need for expanding our circles of caring and our circles of influence. The more diverse perspectives that we have, the more powerful all of our work becomes. So I want to apply this to your work because I’ve read your book a couple of times now, the “7 Rules” [for Positive, Productive Change] and the second rule is honor the past, present, and the people.
Esther [00:02:39] Yeah.
Sean [00:02:40] So this diversity thing kind of plays into that rule a little bit. What prompted you to write that book?
Esther [00:02:46] Well, you know, it’s one of those things, like, you write a book and then you say, “I am never writing another book.” And…
Sean [00:02:54] How many times have you said that yourself because you’ve been pretty prolific?
Esther [00:02:57] Well, three or four. So I have just seen so many change efforts where people plow in tons of money, tons of time, where they, you know, try to give people pep talks. And then when that fails, they berate them and they end up two years later with essentially the same pattern but having, you know, damaged relationships. I’ve seen so many so-called transformations where they spend all this money, they overlay a process, and because they don’t pay attention to the existing pattern and what holds that pattern in place, that pattern reasserts itself. So you can’t just paint something on the top and then expect that pattern to magically shift itself. So that’s why I wrote it, to have a different approach to change, one that acknowledges the humans and acknowledges the complexity of organizations and the need to really pay attention to what is and how we can shift patterns.
Sean [00:04:01] Yeah, that is one of your special skills, I can attest to that, and I see a lot of the patterns that you point out in the book. One that you just mentioned was rule number four, right, attend to your networks. But it is about the people. It’s about expanding the narrative and everything we do is about people at the end of the day. So as I was doing my homework on you, I also noticed you’re pretty close to Johanna Rothman.
Esther [00:04:23] Yeah, we’ve been friends for years.
Sean [00:04:26] She’s been on the pod. I met her on an airplane. I was actually between her and her husband and she kept poking me, like, to chat. She’s like, “well, so what do you do?” I was like embedded in my work and just trying to get this thing done. And it turned out we had the most fascinating, wonderful conversation and became fast friends.
Esther [00:04:45] Oh, that’s fantastic.
Sean [00:04:46] And my next books on my list here are some of the ones that you two have written together.
Esther [00:04:50] So, yeah, well, I met her through her husband. Mark and I were in a workshop together and he introduced me to Johanna and we hit it off. So we’ve done things, workshops and writing and various other sorts of things off and on together for, yeah, 20 years by now. It’s hard to imagine it’s been that long.
Sean [00:05:11] She’s an amazing, amazing soul. She literally was so persistent she just wouldn’t let me be.
Esther [00:05:16] She is one of those people who leaves any gathering with new friends.
Sean [00:05:21] I believe that.
Esther [00:05:22] I, on the other hand, would have left you alone for your work. I would like to sit quietly and do not disturb the other passengers.
Roberta [00:05:33] Awesome, that’s fantastic, Esther. I do want to jump into this question because I think until I read your book, I hadn’t thought about how important this one first principle is, and that is that you assert that vision doesn’t only represent where you’re going, right. We all have a part to play in this. And a solid vision has to acknowledge that the current state of problems and the way that you demonstrate resolution is different for everyone, right. Obstacles will inevitably come in our path, right? We know that that’s the case. But getting to our future state requires that we understand there’s steps along the way, right? It’s not just where you’re going. It’s where you’re starting. It’s who you’re starting with. It’s the potentials that you have, the environment to shape and shift around you. What tools or what practice would you use to help those who are trying to keep vision moving, to keep people moving?
Esther [00:06:34] Well, you know, I think you have to concentrate on where it is you’re heading, you know, the vector of your travel, while you’re also dealing with what’s happening in the day-to-day. So you have to keep a focus on both. And in my experience, people often have a vision that is highly aspirational, but it is not necessarily tied to how they want to be, what difference they want to make for their customers, what difference they want to make in the world, what problem they’re trying to solve. So there are these vague things, like, “we want to be a world-class technical organization.” To what end? For what purpose? Right.
Esther [00:07:19] So I think that the vision that has to be tied to something that people can actually have some resonance with, that it’s at least something that they can see as tangible, if only in their mind’s eye. But, like what I was talking about the first, if people don’t pay attention to what holds the current pattern in place, they’re not likely to be able to reach it. And many, many companies default to training as the way to get to their vision. You know, “if we just train everybody in design thinking, if we train everybody in whatever it is, we’ll get to this desirable thing.” But I actually think it’s much more like growing a forest. So I happen to be married to an ecologist and we spend a lot of time hiking and I think about forests a lot.
Sean [00:08:09] I noticed you use a lot of rainforest analogies.
Esther [00:08:11] Yeah, well, I don’t hike in rainforests very much, mostly northern hardwood forests. So you do not start a forest from rocky ground. You know, if you have rocky ground, some little plant species will take hold, usually something minuscule and tiny, but it has little effect on the environment. It might break up the soil a little bit or it might hold a tiny bit more moisture, which makes it possible for another plant community to take hold, which will alter the environment again. You know, maybe it’s a little taller so there’s more shade, which will affect the humidity, which allows another plant community… And eventually, you get a forest. But you can’t just plant rows and rows and rows of trees. You might get a pine plantation, but you won’t get a forest. Right.
Esther [00:09:00] So I think this is a really important metaphor for us to think about when we have this vision of what we want to achieve, what purpose we want to serve, what problem we want to solve. And we have what our current situation is. We have to create the conditions iteratively for whatever that new thing is to emerge. We have to make the conditions hospitable for whatever it is. If it’s technical excellence, then maybe you have to look at, “people are so slammed they don’t have time to think, how can we create the conditions for people to actually learn how to do this in an excellent way or in a way that has the desired quality or to take time to deeply understand our customers?” Maybe that’s where you start, right. And that creates the environment for something else to take hold. And each little change that you do creates the possibility for something else to emerge.
Sean [00:10:02] My theory on vision is you have to, and I love the way you described it in the book, you have to understand, to the greatest degree possible, your customer and create a shared understanding of, who does this organization, who does this team exist to serve? And what do they care about? And then, once you understand them, you have the right to ask yourselves and to organize what problems you can possibly go and solve for them with the skills and the tools, and the context that you have. And to me, that constitutes a powerful vision, like, when you have a clear understanding of the current landscape, like, “here’s who we exist to serve here’s the problem is we exist to solve,” and knowing what success looks like, that painted a picture of the future that we want to create, we may never actually get there. That’s the thing we want to accomplish. If you do it well, I’ve found it serves to motivate the team.
Esther [00:10:54] Yeah. Much more so than, “oh, we want to be number one in our market.” That motivates the people who are going to be financially rewarded by the stock market for being number one in their market, but it typically doesn’t motivate a lot of other people. You know, they want to solve a really significant problem, whether it’s a technical problem or a human problem, or they want to make life better for people in some way.
Roberta [00:11:21] Esther, earlier you had mentioned that if we don’t resolve those patterns that have formed and are sometimes invisible until you try a new approach and realize that repeat is happening, how do you identify those patterns more quickly? Is there any experiences that you have that you can share with us where you’ve had those light bulb moments and there have been others where maybe it’s taken a little bit longer or the pattern behavior didn’t really emerge but you know there’s something there?
Esther [00:11:48] Well, I would say… So I have to go in a little roundabout here. So in most organizations, people are just flooded with events and information and just stuff happening every single day that they have to respond to. So there’s all this stuff coming at them super fast every day. I think about those as events. Those are things that are happening in the know. And patterns are things that you can discern if you take a longer temporal view or a greater spatial view. So you can sometimes model patterns if you look at existing data in the organization. So, you know, what has the performance been on, you know, projects. Is every single project late and over budget? Well, that’s a pattern, right? Or is our productivity going down after each reorg? I mean, those are things you can easily measure and model to see what the patterns are.
Esther [00:12:44] And then the patterns are generated by structures and other policies and processes that exist in the organization. So then you have to figure out how they relate to each other, what contributes to that pattern. And then you just, you work on them as you can. You can’t always get all of them directly. But if you can figure out the ones where you have some control over it, at least to influence it, and then you can have some sense that this is affecting other things… Because they’re almost always entangled. So you figure out, “well this one looks like it will affect camaraderie,” then that’s how you start. You work on those. But modeling, if you have data, is helpful. Sometimes I use techniques out of Glenda Eoyang’s work to do some modeling, not necessarily about things that are quantifiable, but if I’m seeing strange patterns of interaction among people looking at a workflow through the organization, that’s another way to see patterns.
Sean [00:13:41] I say it’s a key leadership skill is this ability to figure out at what level of resolution you’re looking for the problem, to be able to zoom out and be able to zoom in. That’s where I think a lot of these models, like they’re useful, but only if you have the ability to zoom out with them and zoom in at the right resolution, you know.
Esther [00:14:00] Yeah, that’s an interesting one, because I think we have been taught, partly explicitly and partly just by the structures that are around us, that people are always the problem. You know, people are easy to see and they’re easy to point to.
Sean [00:14:15] Easy to blame.
Roberta [00:14:15] And blame. Yeah, they’re easy to blame. “You know, the reason our projects are late is because our project managers are crap,” or “the reason that our products aren’t well-received is because our development teams are crap,” which is very seldom the case. But it’s easy to point there rather than look at some of the structural things and look at some of the difficult issues that might be uncomfortable to face up to personally.
Roberta [00:14:41] Yeah, it’s interesting that you picked this right to our second question, which is great, because right now we’re in the process of doing some reorganization ourselves and it’s sticky with people because relationships have been formed and built. And, you know, even if it’s for positive growth, it sometimes is still met with anxiety and it leads to stress. So from your experience as a developer and throughout your career, when you look at organizations that have focused on building software, have you seen any structures out there that make more sense than others to help facilitate that work and also establish some of those relationships that might not always be org chart related?
Esther [00:15:29] Well, I think there are a couple of different ways to answer that. In general, I think cross-functional teams are super helpful. You get a broader point of view, you’re less likely to miss, you know, major things that you need to be thinking about. So I generally like to have cross-functional teams. But most organizational structures can work when the incentives are not designed to prohibit working together. So I see a lot of organizations where the incentives for one group are directly in conflict with the incentives or another group. And the more the structures and the reporting relationships and the incentives reinforce that difference and amplify that difference and reinforce it, the less likely it is you’ll be able to have cross-functional collaboration between those groups. You know, they’ll end up saying, “oh, well we’re doing a value stream,” but their value stream starts and ends in their silo. It becomes very difficult for people to look across the whole thing.
Sean [00:16:31] We’re in the agency business and this is something we struggle with every single day, right.
Roberta [00:16:35] Sure.
Sean [00:16:35] You got the clients incentivized to get as much feature functionality as they can for the dollars they’re spending. We’re incentivized to maximize our billing. And if we don’t get those incentives lined up properly and get the teams motivated about the right things, it doesn’t work. And that’s one of the things we figured out early on. It’s part of our secret sauce, for sure. And then on the inside of that, you have this need for visibility and revenue. And we have people, you know, I’ve got to make sure they’re incentivized to grow and learn and do the things that they have to do to build a successful agency. You know, all of those incentives are like so important to understand and to actively, openly talk about, be vulnerable with, and to make sure that we’re playing the long game, you know.
Esther [00:17:18] Yeah, people get really attached to their turf, right. Particularly when the incentives are pushing them that way and when the structures and the incentives kind of propel people towards collaboration and innovation, they’ll go that way. But our traditional structures, very often, you know, they could work, but the incentive structures make it very difficult for them to work.
Sean [00:17:45] Yeah, sometimes you don’t have full control over those incentive structures. So I think the most important thing is to openly and vulnerably talk about them so that we can really deal with the human side of our production and our teams and the work output.
Esther [00:17:59] Yeah, absolutely. I mean, there’s one company I worked in where their job descriptions were so narrow that people were incented to “hone my skills in this narrow little area and any time I spent working with someone else or any time I spent developing near neighbors skills would in the end work against me at review time and promotion time.” That was a structure that was there and the incentive system that was there and it would have taken the approval of, I think, 17 vice presidents and an act of God to change it.
Esther [00:18:35] But we contextualized it. So we just started talking about, you know, “this is what we’re trying to do and this is what your job description is and this is what we’re trying to accomplish here. So this is how we would look at this in this particular case and what we’re trying to accomplish in our group. And this is what we’ll be talking about when it comes to promotions, too.” So we didn’t worry about changing the job descriptions because that would have, you know, people would have been dead and gone by the time we got that taken care of. But you just, you talk about it. Just like you said, you talk about it openly and honestly and you talk about people’s fears that, well, “if I contribute to this team in this way, is it going to hurt me when it comes to getting a promotion?” We just have to have those conversations.
Sean [00:19:22] Yeah. As a leader, it’s the hardest thing: titles, role descriptions. Like you have to have boundaries so you can have open conversations, but at the same time, you don’t want them to restrict people from being successful together. And that’s often what happens when people start to play the political game, you know?
Esther [00:19:37] Yeah. I think traditional job descriptions strike me often as almost like functional specs for humans. Right. And there’s this little box and you have your skills and your responsibilities in this little box. But real work doesn’t happen that way. You know, there’s all that white space in between and the collaboration and sharing of ideas. And so I think of jobs is like being more like a fried egg, you know, there’s the yolk or the egg gold in the middle that might be some core set of skills, but everything else you do, it conforms to the shape of the people around you and the work that you’re trying to do.
Sean [00:20:14] Love that analogy.
Esther [00:20:15] Now we’re hungry. Now we want an egg.
Roberta [00:20:19] So, when a company is looking to initiate a large change, where and when do you recommend that they begin their communication plan?
Esther [00:20:29] Well, first I would say, if you are planning a large change, the first person you have to communicate is with yourself and think about what are all the tiny little steps you can do to move it forward. Right. There’s actually some research that shows that, oh, if you want sustainable change, you do small changes. So after years of people talking about making these big changes, it’s like finally, finally micro shifts. So I would say, you know, talk about where you want to go and that there’s a lot of steps on the journey and you cannot find them all up-front. That’s a fool’s errand. And then you work on small changes because, you know, big changes feel like an existential threat. And little tiny ones, they don’t. I mean, it might cause a little blip, but it’s not going to be a major disruption. And so you communicate, you know, “where do we want to go? And this is what we’re working on now and there’s some stuff we’re going to have to figure out together. We don’t have all the answers.”
Roberta [00:21:27] And how do you, I’m not going to use the word convince because that’s not the right emotion here. But when you’re trying to influence folks who may have a resistant attitude or have concerns that you haven’t necessarily identified yet, how do you start with them? Do you identify them individually? Do you address the masses and use use cases or analogies? What is your approach for helping people get what they need to feel comfortable and work towards the same goal?
Esther [00:22:02] Well, I listen to them. You know, I mean, because I might learn something super useful from their concerns, something that would make a huge difference in what I’m trying to accomplish. And I treat their concerns as valid. I don’t necessarily agree with them, but you have to listen to what the concerns are and find out, you know, kind of what’s underneath the concern. And then sometimes you can say, “well, yeah, that’s true, and this is the benefit we hope to get.” Or, “yeah, that’s true and there is going to be a loss; it is going to be uncomfortable.” You know, acknowledge that almost always include some negative space for a change. So, you know, I think some of that can happen one-on-one. Some of it needs to happen, you know, be dispersed through the organization by people who are working on the change. Some of it can happen in public settings where people just get to talk about what their concerns are.
Sean [00:22:56] The theme of this podcast is listening and communication, right?
Esther [00:23:00] Well, there you go.
Sean [00:23:02] All right, white space, you had a cool idea in your book in terms of conversations and context, but you talk about white space in the org chart. I just want to hear your thoughts on that because I think those are valuable.
Esther [00:23:12] Well, I mean, in some ways that’s related to the egg yolk thing. It’s all this white space, the communication and the coordination and the thinking together that happens that doesn’t show up in an org chart at all. And that’s a sort of fractal thing. You know, you see it in the networks that exist in the white space, right. They don’t show up on your formal org chart, but they’re essential to getting work done.
Sean [00:23:33] Those informal networks.
Esther [00:23:34] Yeah, but you also see it on well-functioning teams. There’s all sorts of white space roles that don’t get called out in anybody’s job description, but they form the kind of the, some of it’s the social glue, some of it’s informal roles that people take like, you know, organizing stuff. And these are not formal roles. They’re not titles. Usually they just emerge as needs show up. You know, someone pays attention to how are the relationships working? Someone pays attention to, do we have enough ideas? You know, so that white space exists on multiple levels in the organization and without it, they don’t work. But we like that nice clean org chart and our nice process diagrams. They’re comforting. They make it seem like everything’s nice and neat. It’s actually kind of messy.
Roberta [00:24:21] And there’s a lot of value in that messiness, too, right. That’s the part of the organization where, when the process breaks down, work still moves through because you’ve got each other’s backs, right?
Esther [00:24:34] Yeah. And that’s where the juice is, you know.
Roberta [00:24:37] Mm-hmm. So we talk a lot in our team about innovation, and we always like to get definitions and what these words mean to people. So if we asked you your take on innovation, what would your answer be?
Sean [00:24:50] How would you define it?
Roberta [00:24:52] Oh, yeah, true.
Esther [00:24:54] How would I define innovation? Well, I would Google the definition and read it to you… Well, I think it’s in finding novel solutions to problems that people are experiencing or novel ideas that create the possibility for something new. So, you know, a lot of the innovations that exist for us today came about to solve a particular problem. And another class of them was just, you know, in imagination. But they are both, in some ways, either creating novel possibilities or finding a novel solution to an existing problem.
Sean [00:25:32] Love that definition. Last question for you.
Esther [00:25:34] OK.
Sean [00:25:34] What are you reading or listening to these days that you would recommend to other product readers? Other than your own books of course.
Esther [00:25:43] So when you said, “what are you reading,” of course, the first thing that came to mind was I’m reading medieval history.
Sean [00:25:49] That’s a great intro.
Esther [00:25:51] This is not a typical history and I’m listening to it. Right. Most history talks about, you know, looking backward from a nation-state, kind of tracing backward to all of the events that led up to that nation-state. You know, you look at French history and they talk about Agincourt and they talk about, you know, Kressy and all of these battles and so forth that happened. And it’s like it’s somehow a normal, natural, and predictable evolution. But this particular history is saying, “well, let’s start from Rome and let’s look at the conditions and what emerged from those conditions.”.
Esther [00:26:26] So, you know, in Rome, there was a pretty dense network of cities and well-done roads to get between them. And that allowed certain things to emerge in the southern part of Europe. And when you crossed certain rivers, which was the boundaries of the Roman Empire, you go to countries in northern Europe, something completely different emerged because they didn’t have this dense network of cities and roads and taxation played into it and a whole bunch of things. But what’s interesting to me about that, that I think is potentially useful for product people, is it talks again about how things emerge and what conditions are present that will allow for something to take hold and to take off. So how can we create the conditions to be deeply attuned to our customers? And what are the conditions that exist in our customers’ lives? And how might we shift those conditions in such a way that would allow our product to become an integral part of their life?
Sean [00:27:30] So the lesson here that I’m taking from your recommendation goes back to the thing we started this conversation with, about diversity. I think it’s important for product leaders, in particular, people who are supposed to be in this creative space helping produce creative products, to have some other things that they’re doing and thinking about in their lives, and all of this stuff matters in creating or fostering diverse ways of thinking. You’re tapping into history here. I think there’s things to be learned from every industry. And I think it’s important to keep that sort of creative flow, what you put into your mind, because what you put in is what you get out. Right?
Esther [00:28:07] And maybe a less weird example would be I’m reading Chatter, which is about how we manage our inner voices and how we can gain some psychological distance and become calmer, in which case we’re more creative and we’re more able to relate to other people.
Sean [00:28:26] I love it. All right. Well, thank you, Esther. It’s been a fantastic time interviewing you.
Esther [00:28:31] It has been delightful. Thank you for having me.
Roberta [00:28:34] I truly enjoyed the prep work.
Esther [00:28:36] Yeah, it was fun.
Sean [00:28:38] We had a lot of conversations about it before the podcast, which is not always the case. So really, really great content that you’re putting out there. And I wanted to personally thank you for your contributions to our industry because they are spectacular and enduring.
Esther [00:28:51] And I hope I can keep contributing for some time.
Sean [00:28:55] Excellent. Even if it means writing another book?
Esther [00:28:59] Well, it hasn’t been announced yet, but I signed to do a second edition of a book that I co-wrote in 2006.
Sean [00:29:07] Congratulations.
Roberta [00:29:08] Fabulous.
Esther [00:29:09] Well, I never thought I’d do that, but here I am.
Sean [00:29:14] Well, thank you, Esther.
Esther [00:29:15] Yeah, my pleasure.
Paul [00:29:19] Well, that’s it for today. In line with our goals of transparency and listening, we really want to hear from you. Sean and I are committed to reading every piece of feedback that we get. So please leave a comment or a rating wherever you’re listening to this podcast. Not only does it help us continue to improve, but it also helps the show climb up the rankings so that we can help other listeners move, touch, and inspire the world, just like you’re doing. Thanks, everyone. We’ll see you next episode.