Depthfinding: Sky - Threats and Opportunities

Summary

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Episode Overview

Episode Title: Depthfinding: Sky – Threats and Opportunities
Hosts: Rodney Evans and Sam Spurlin
Date: January 27, 2025
Podcast: At Work with The Ready

In this episode, Rodney and Sam dive into the "sky" layer of their Depthfinding framework—a metaphor for the external forces impacting organizations, such as technology shifts, marketplace dynamics, climate, and politics. They explore why organizations struggle to pay attention to external change, the consequences of that inattention, and practical approaches to scanning for both threats and opportunities. With a mix of organizational examples and personal reflection, they pull apart why most teams are reactive (or oblivious) and outline ways to make “sky work” a healthy and habitual part of both personal and organizational practices.

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Key Discussion Points and Insights

1. The "Sky" in Depthfinding: A Metaphor for the External Why

• The "sky" encompasses all external forces—technological, social, economic, political, and environmental—that organizations exist within and must respond to if they’re to survive and thrive ([03:00]–[05:00]).
• Most organizations are "internally myopic," rarely looking up to consider what’s changing around them until a crisis emerges.
• Rodney: "The hard reality of being in especially a leadership role in any business is like every business decays. It just does. And the way that you know how it's going to decay is by paying attention to what's going on out there." ([06:26])

2. Sky as Both Threats and Opportunities

• While most leaders instinctively notice threats (the dinosaur or meteor coming for your business), the sky is equally full of underexploited opportunities ([08:30]–[10:30]).
• Human psychology and organizational habits tend to focus on pain avoidance vs. gain pursuit, often leaving innovation on the table.
• Sam: "There’s this whole other side, the whole opportunity cost of things not done that are also in the sky. And you don’t know to pursue those if you’re not regularly engaging with it..." ([08:33])

3. Sky is Multilayered and Personal

• Every function and role has its own unique "sky": the external forces shaping HR aren't the same as those shaping finance or product teams ([11:00]–[12:50]).
• Healthy organizations encourage teams to track trends relevant to their unique context.

4. Sensemaking is Social, Not Solitary

• Effective sky-scanning isn’t a solo act. Group sensemaking—coming together to share, debate, and synthesize external signals—is vital ([13:36]–[14:45]).
• "Depth finding is a team sport," says Rodney. The interplay of individual curiosity and collective reflection distinguishes robust sky work.

5. Texture Over Checklists

• It’s not just about tracking headlines or making trend lists. Successful leaders and teams develop "texture"—an intuition built from ongoing engagement and deep, diverse information ([14:37]–[15:28]).
• Quick fixes or borrowed strategy frameworks often miss this richness.

6. Why Sky Work Often Fails

• The "anti-example": Leadership teams express a desire to do strategic, sky-focused work, but lack rituals, rhythms, or space to actually engage in it ([20:43]–[24:00]).
• Strategy development becomes performative: “By May, nobody can find the deck. And by, you know, September we're talking about next year's and with like no memory of what it was before." – Sam ([23:27])
• Disconnect between declared aims and true external drivers leads to generic, unimpactful solutions.

7. Making Sky Work Part of the Rhythm

• Carve out explicit time for sky work, e.g., Friday sessions to discuss external articles or trends ([27:44]–[28:13]).
• Importantly, talk to people outside your organization to avoid echo chambers.

8. Individual and Collective Practices

• There’s much individuals can do: reading, journaling, having prediction and review cycles, using AI tools to surface personalized trend analysis ([29:07]–[33:48]).
• But collective synthesis—building a shared sense of threats and opportunities—is critical for real impact.

9. The “Ready” Example: Practicing What They Preach

• The Ready has redesigned much of its own operating rhythm to integrate sky work, dedicating ~50% of its time on external sensing ([34:00]–[38:42]).
• Rodney describes using scenario planning, red teaming, and engaging all members to collectively sense where their sector is going.
• Adapting to dwindling client appetite for “ways of working” required them to shift toward helping on clearly sky-connected problems.

10. Creative, Imaginative Sky Work

• Reading fiction (especially science fiction) can broaden leaders’ ability to imagine futures—a helpful practice for sky work ([18:03]–[19:23]).
• Sam: "A leader who has a robust fiction reading habit…is likely to have a more sensitive and nuanced take on the sky..." ([18:03])

11. Don’t Rush into Execution

• Resist the urge to immediately “action” every trend. Stew, experiment, and let clarity emerge ([41:19]–[44:41]).
• Stew vs. omelette metaphor: "We want stew in this. We want to develop those flavors." – Sam ([43:42])

12. Impact at the Individual Level

• Individuals who invest in sky work feel more confident and deliberate, even (especially) when making bold bets ([47:01]).

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Notable Quotes & Memorable Moments

• On decay and sky vigilance:
  "Every business decays. It just does. And the way that you know how it's going to decay is by paying attention to what's going on out there..." – Rodney ([06:26])

• On collective sensemaking:
  "It is through the way that I talk about my interpretation of the sky and the way you talk about your interpretation of the sky that we actually create a new and better different take on what is actually happening..." – Sam ([12:50])

• On performative strategy:
  "February, we're all stoked about the new strategy. By May, nobody can find the deck. And by September, we're talking about next year's with no memory of what it was before." – Sam ([23:27])

• On the necessity but rarity of 'sky work':
  "...I just don't think that most leadership teams, in particular, make a lot of time for it." – Rodney ([14:37])

• On individual sky practices:
  "There's so much to be done as an individual where you don't need the buy-in of literally anybody else to really level up your ability to interact with the sky." – Sam ([29:07])

• On stew versus omelette as a change metaphor:
  "We're making a stew here, not making an omelette... Both are delicious, but only one is fast." – Sam & Rodney ([43:42])

• On imaginative practices:
  "Sky practices are imaginative in nature... you have to then imagine a future that may or may not exist." – Rodney ([19:23])

• On the “magic” of shared sky work:
  "When one of us posits a guess at what the play is, the rest of us go like, 'Yeah, that seems right.'...And that feels like magic. That feels like a magic trick." – Rodney ([46:57])

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Timestamps for Important Segments

• 03:00–05:15: Introduction to the “sky” metaphor and why most orgs ignore it
• 06:26: Rodney on the inevitability of decay and the "paranoia" needed to avoid it
• 08:33: Sam on opportunity costs and the human tendency to notice threats
• 11:04–12:50: Multiple skies – Every function/team faces its own unique set of threats/opportunities
• 13:36–14:45: Why group sensemaking is superior to top-down sky analysis
• 18:03–19:23: The value of fiction and imagination in future-facing leadership
• 20:43–24:00: The “anti-example” where leadership wishes for strategy but refuses to build the practices
• 27:44–29:07: Practical tips for building sky work into the operating rhythm
• 34:00–38:42: How The Ready has institutionalized sky work internally
• 41:19–44:41: Letting sensemaking stew—don’t rush into execution
• 46:57: The magic of synchronized collective understanding
• 47:01: Confidence that comes from deliberate sky work

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Practical Recommendations & Takeaways

• Don’t rely on structure alone (e.g., OKRs, matrix reporting) for sky work—build explicit, recurring practices.
• Balance the focus on opportunity and threat; don’t default to fear alone.
• Encourage individual curiosity AND collective sensemaking; both are necessary for resilient strategy.
• Read widely—including fiction—to build imagination muscles.
• Make “external sensing” a rhythm, not a one-off; talk to outsiders, use liberating structures, and let new direction emerge organically.
• Mix individual and organizational data sources—client feedback, team member insights, competitor moves, external advisors, publicly available information.
• Give sky scenarios time to percolate rather than forcing instant plans and actions.

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The episode is a rich, candid exploration of how teams can radically improve by building regular, creative "sky work" into their DNA—while calling out why so many fail to do so. Whether you’re a leader, team member, or consultant, the episode offers actionable wisdom on making external awareness an engine for adaptive, intentional, and meaningful change.

Transcript

[A]

Hey, everybody. Welcome back to the show. I'm Rodney Evans and that guy, host vacation is my co host, Sam Sperlin.

[B]

So refreshed. So just ready to go.

[A]

Just back from that cruise life.

[B]

That's right.

[A]

I love it. We didn't get to really talk about what you did on your cruise, but I'm imagining like drinking out of a coconut and playing shuffleboard on the lido deck. Am I close?

[B]

You're not too far off. I mostly just hung out where the free hot dogs were.

[A]

On brand. Well, welcome back to At Work with the Ready. This is a podcast about modernizing organizations as the future of work meets the present moment.

[B]

And this is our second episode of our miniseries on depth finding.

[A]

Yeah, I just listened to the first one and I really enjoyed it. So I'm looking forward to getting into it again. But before we dive in, we must check in. Sam, what you got?

[B]

What I got for us is what did Jackie get you for Christmas?

[A]

I love that we're doing this because Jack doesn't know and he has no control and he's already left the recording room, so he can't stop us. Jack surprised me with a very large box that was a variety pack of small, Deep river potato chips. One of the topics that Jack and I bonded over earliest on in our friendship slash coworkership was our shared love of potato chips. And if you could see the number of text exchanges that Jack and I have had, sending each other photos of potato chip. It's a lot. Like 20% of our relationship content is potato chip based. So I'm working my way through the Deep river snacks and the unboxing video that I sent to you. Like, I could not have been more thrilled.

[B]

Yeah, it was maybe the happiest I've ever seen you.

[A]

It was the happiest I've ever been.

[B]

Nice.

[A]

What did Jack get you for Christmas, Sam?

[B]

Well, there's a theme here, a food based theme, because Jack bought me something that I didn't even know existed, which is Snickers as big as my forearm.

[A]

It was a.

[B]

It was a loaf of Snickers. Basically. You have to, like, cut slices off of it. And boy howdy, have I been cutting slices off of it. It is. I have discovered that this is not a thing I can keep in my apartment because I just keep it out on a cutting board. And as I walk by, I just cut off almost entire Snickers at a time. And that is not like a thing that should become part of my routine.

[A]

Yeah, that's not just like Finger food.

[B]

No, it's not. And I literally today just finished the second one.

[A]

Wow. Well, our presents were as thoughtful as Jack always is and also so delicious and not the most healthy. It doesn't matter. No, because we're having a great time.

[B]

Thanks, Jack.

[A]

Thanks, Jack. So this week we are going to talk a little bit about the sky. If you remember from last week, that's the weather that's floating above your ocean in depth finding. And specifically we want to talk about the pace of change in the sky. Because what we find in our work is that the external forces that are acting on your organization, whether that's technology, changes in the labor market, changes in the political climate, changes in the actual climate, things are moving out there faster than then we are able to adapt in here. And that disconnect, I mean, I would argue is a huge reason for organizational change, for organizational transformation, for organizational debt, for tension, for burnout, for a million other things. What we know is that responses to what is happening in the sky are always cross functional, as are the strategies that are going to be required to really adapt to any kind of framework force like the one that I mentioned. But our organizations are not really designed to do that. And no, like your matrix reporting structure will not save you, nor will your okrs. So we're going to talk today about how these sort of novel problems addressed with TRAD moves are just making everything worse. And that's sort of like the primer that's the lead in. So I guess like, I'll just start by asking you, Sam, what do you see particularly in your client work around the sky stuff.

[B]

Yeah. So a thought that I had literally for the first time as you were just kind of doing that lead in there is that I think this metaphor of the sky in the zones is great because like the sky in actual life, I think most organizations don't think about it very much. Like it's always there and it's always affecting things, but very rarely, maybe only when things are particularly difficult, do we actually become aware of what is happening around us. And that's the overarching thing that I see in most of the clients that I work with, is just a general lack of conscious attention and time spent on trying to understand what is happening in the sky and why.

[A]

Yeah, I agree with you. I see the same thing. Why do you think that is?

[B]

So two things come to mind for me and I think they'll probably show up in a lot of the examples that we talk about today. One is that I think most organizations are so well suited to consume all available attention on internal stuff. Just being a person in an organization will take up all of your attention and none of it will be left over for the stuff that feels outside of, you know, what you have to deal with on your day to day. And then the second thing is that I think sometimes we avoid the sky because if we're truly interacting with and understanding with and trying to make sense of what is happening in the sky, we will be forced to ask very uncomfortable questions about what we are and aren't doing in our organizations. And I think a lot of times we'd rather just kind of let sleeping dogs lie and not take a look up at the sky and just kind of operate with the inertia that we naturally have in most organizations.

[A]

I think that's true. And you know, I think the hard reality is of being in especially a leadership role in any business is like every business decays. It just does. And the way that you know how it's going to decay is by paying attention to what's going on out there. And the way that you build the bridge to the next thing is also by paying attention to what's going on out there. But in order to do that, well, you have to at least admit that, like your thing that has been successful or gotten you to this point or whatever is going to die. Everything does. And so it's like I was asking a friend who's an exec at a company for advice about a particular problem that I was having. And she was like, I just don't think that the person that you're describing is paranoid enough for being in that role. And she was talking about external paranoia. And I don't think that it is useful or healthy to be in a position where you believe that the sky is falling. You know, like, nobody wants that. And you also don't want to be like, you know, the Kodak story that misses the digital revolution.

[B]

Right.

[A]

And it's not that hard to miss. Like to your point, day jobs are busy. Our organizations, particularly older organizations, which is a lot of our clients, are so rife with process and bureaucracy. That was built for a different age. That was built for the information age, probably, but even in some cases the industrial age, like all of the time and attention of leadership is generally going to servicing the organization so that it functions in squeezing as much possible value out of the existing core business as possible. And then the whatever is maybe left over gets thrown at what the fuck is going on out there.

[B]

That's why we have an Innovation team.

[A]

Innovation team. Or like why we have a strategy consultancy to like tell us what signals to pay attention to and we're going to talk about this. But I also just think like it is a habit to build that's not so easy to build.

[B]

You made a point that I think we should emphasize. Because when I first started thinking about depth finding and the sky in particular, my mind immediately goes to the threats part of it. Like this is where the threats live, so be aware of it. Scary dinosaurs and birds are in the sky and they are coming for you. But there are also opportunities. And I think what organizations are best at are probably noticing threats because that's where you have the fear. But there's this whole other side, the whole opportunity cost of things not done that are also in the sky. And you don't know to pursue those if you're not regularly engaging with it and trying to make sense of what is happening around you from an opportunities perspective.

[A]

Yeah, and it's funny because I listened to our first episode and I realized like you and I both constantly refer to the Midnight Zone as being negative feelings and actually like it was not defined that way. Like it was defined as the full lived experience that everybody has internally. I know maybe this is more about us than it is about the world, but I think the sky is the same thing and, and what's interest interesting that I'm realizing literally in this moment is the way we describe this in the framework is the sky is your external why. It is the reason that you are going to aim for whatever you're going to aim for in the Sunshine Zone. And the Midnight Zone is your internal why. And so that's where your motivations lie. And like, you know, as a psychology scholar, like whys are pains or gains and humans have a tendency to filter for pain or to anchor to pain or to over index on pain rather than gain. And it's interesting because when I was thinking about this, the first sky examples that came to mind were opportunities like the opportunity for an acquisition, the opportunity for AI enabled, blah blah, the opportunity for incubating a new product. But as soon as we start talking about it, the things that come up are existential threats first. And I think that's like just human nature.

[B]

Yeah, it's not about like not having one or the other, but having like a balance of both and like using each as your entry point into thinking about things like, all right, what are the opportunities? And then that leads to threads and then you can also do it the other way around as well. One of the things that I've been thinking about with sky is that right now we keep saying, like, the sky, which is good shorthand and, like, maybe is the best way to describe it. But I had the idea that we're really kind of talking about lots of different skies.

[A]

Totally.

[B]

The way we've been talking about it, I think, is kind of the organization's sky, where that is across everything. But I'm wondering, you know, what does the sky look like for a functional leader? Like, what's the HR sky right now? What's going on in the HR world? Repeat for any and every function in an organization. Do you think that is a useful way to think about SKY as well?

[A]

I absolutely do. And this is where other models that I've seen that talk about the external environment really anchor to, like, the external environment of the organization. And I think that usually puts us in a very, like, industry state of mind. But to your point, I think everybody's sky is probably a little bit different. And I think in the healthiest organizations that I have seen and been part of, different teams and different leaders are paying attention to different trends and different forces. And like, I would hope that the finance folks in a large organization are looking at slightly different articles than the product folks, because the forces acting on any organization are going to be different. And then as you get further and further toward the center of the organization, your customer is different. And so those are different skies. Like, HR is a great example. What was expected of HR by its organizational sky 20 years ago is very different than what's expected today. I was in a conversation with somebody yesterday, and she was like, yeah, all I'm hearing now is like, be in strategic workforce planning. Workforce planning, workforce planning. And she's like, you know, 10 years ago, workforce planning wasn't really the thing.

[B]

Yeah, you're helping me see how kind of the individual practice collected together creates something different. So I was thinking about, like, man, the sky is like, really like an individual thing. Like, it's up for each of us to do our individual work to understand the sky, which I. I do think it is. But it is through the way that I talk about my interpretation of the sky and the way you talk about your interpretation of the sky that we actually create a new and better different take on, like, what is actually happening and, you know, bring in other members of the team and have this going on across the organization. You have this collective sense making of what is actually happening more so than any one person could articulate or hope to understand on their own.

[A]

Totally. And that's why, like, depth finding is a team sport and it's meant to be like anything we've ever done at the ready. Like the idea of participation and of divergence and then convergence and coherence. Like, those ideas, I think are evergreen and this is a place where. Done well. You get out of the idea that there is one right answer or one correct response to what's happening in the external environment because one CEO was told by one. One board that it must be so. And you get into a, honestly, like a more creative space that's like, what quiet signals should we be paying attention to? Like, I have a lot of conversations where someone will point out something that like, feels pretty edgy, but intuitively I'm like, that's something to watch. And like, this is where it's like the texture of this practice comes into play. And to your point, I just don't think that most leadership teams in particular make a lot of time for it.

[B]

And what you're not talking about there is just like, well, the sky is not just. Here's the list of the trends that we have to be aware of. I like to use the word texture because I feel like we're talking about a much more nuanced, almost tactile experience of you've been interacting with what is happening in your discipline, in your function, in your area of expertise in your industry on such an ongoing level for enough time. Time that you can even have an intuition. Nobody has an intuition about a trend that they only know the headline for. Like, and if you do, then I don't trust your intuition at all. Because it's not basic.

[A]

Exactly.

[B]

But the slow ongoing accrual of knowledge and experience and takes.

[A]

Yeah.

[B]

Your world. That is interesting. I think that is more so what we're talking about.

[A]

Absolutely. And I think that's how we get smart on what to respond to. You know, you said something when we were planning this app yesterday about transformation projects that we have done at the ready that did have a sky based. Why? In contrast with those that didn't.

[B]

Yeah.

[A]

And I thought that was really interesting.

[B]

Yeah. You seem to agree with my take.

[A]

I do.

[B]

That's all I gotta roll with.

[A]

Endorsed.

[B]

Basically, we have some projects where we are coming in and there is a very real threat or opportunity in the organization sky and that has kicked off some sort of initiative or some sort of effort that has resulted in us coming in to help with it. And those projects contrasted to, you know, somebody in an organization, like, had an idea or there's Some sort of just purely internal thing that they're trying to fix. Those projects not having quite the same staying power or not even that. It's like the ability to commandeer the attention of people in that organization. It's much easier to get people to make time to work with you when it's connected to a very real sky thing than it is if it is purely just an internal. Like, wouldn't it be nice if we could make things better? Which is hard for me to say because I am like super motivated by like making just internal shit better.

[A]

Totally.

[B]

What's better than that? But if you haven't connected that to something larger, I do see those projects not necessarily sticking around.

[A]

Yeah, I just had a conversation with someone right before the holidays who had wanted to work together about a year ago and sort of like didn't have the juice to get it done. And now they just announced a. A really significant acquisition and she's like, well, now everybody sees the particular way in which we're fucked. So like, now we can.

[B]

Now we can do it.

[A]

Yeah, now we can do it. Like, same teams, same tensions, same o. Same almost everything. Except now there is like a sky based lever that is shaping everything that happens below.

[B]

Yeah, no, I. I love that. I have so many more things I want to say about the sky, but I'm wondering if they're best saved for our examples. What. What do you think?

[A]

Yeah, save. Save your stuff. There was something in here that said a shower thought that I didn't read. So you're going to put that in your. I don't know.

[B]

All right, I'm going to. I'm just going to hit you with a thought. Maybe we'll come back to it.

[A]

Okay.

[B]

But the thought that I was having is that if you think about the sky as kind of the context in which the content of the organization reacts to and it's the context for everything is the sky. What it made me think about is like things like the liberal arts, something like fiction, like a leader who has a robust fiction reading habit who engages with things like that. I think I want to argue that they are likely to have a more sensitive and nuanced take on the sky, as we have been talking about it, than somebody who completely doesn't. And I'm. That's not saying you have to read a bunch of fiction in order to like get the sky, but I'm saying it doesn't hurt. And I don't know, I'm just curious of like how that hits you.

[A]

I mean, the first sky practice that I started when I took this role was a practice of consuming science fiction, which I had never done before and I don't particularly enjoy, but it just felt like to do this job well, it was really important.

[B]

Yeah, okay, that's cool. Like, yeah, read some fiction, and maybe that helps you think about what is happening socially or economically a little bit differently in your world as well.

[A]

Well, I think that, like, sky practices are imaginative in nature because you can use data and you can use history and you can use patterns, but you have to then imagine a future that may or may not exist. And if you spend no time exercising the muscle of imagination, it's gonna be super hard.

[B]

Yeah.

[A]

Yeah, I love that.

[B]

Yeah, that's cool. All right, well, shower thought has graduated to actual thought. I don't know. Aren't lesser, but podcast thought. There you go.

[A]

Okay. So from here, what I really wanted to do to start to give people a little bit of texture around this one, is just talk about a couple of examples where the big event that led to a whole bunch of other stuff further down was a Sky thing, or if it wasn't a big event, because it isn't always, sometimes to your exact point. It is a sharpened perspective that emerges over a long period of consideration and consumption and discussion and debate of what is happening out there. But regardless, we have a couple of examples to talk through just to, like, give you a sense of how we see sky stuff relating to the rest of the depths. So why don't you kick us off? I feel like you have an interesting.

[B]

Mine is like an anti example.

[A]

Yeah. Yours is an example of what not to do. Well, that's all right.

[B]

The example here, when I thought back through my last couple of years of projects, especially projects that involved interacting or really working very closely with executive leadership teams, the thing that united a lot of these experiences was a stated desire from that executive leadership team to do, like, more strategy work, to think bigger picture, and basically none of them having any sort of rhythm or practices or rituals around that work. So this kind of composite example is really the example of the lack of sky work.

[A]

Yep.

[B]

You'll have to help me kind of go through this because in some ways it's hard to talk about, because we're talking about the lack of a thing. But let me just kind of describe what was going on in most of these projects, then we'll play around with it.

[A]

Yeah, cool.

[B]

So almost universally, these leadership teams on their own, kind of identified this as a gap. Like, I find that most senior leaders, when asked will say that they don't spend enough time kind of just thinking big picture and trying to sense what is happening. We don't have to push them into that observation.

[A]

Yeah, they're not. Most of them aren't like, no, no, no, we're dialed.

[B]

Yeah. And we talked a little bit about why that doesn't happen. You know, the, the most number one answer for all of them is that all of these leaders spend all of their time dealing with shit in their own organization. So like my first thing is like if you want to do more sky work, there's an element of like fixing your house.

[A]

Yeah.

[B]

If you spend all your time dealing with escalations and broken ass systems and interpersonal conflict, like when and where and how are you supposed to have the energy to be like, like what does this science fiction book tell us about what we could be doing in the future?

[A]

If your Twilight zone has no practices for attending to or making sense of or responding to what's happening in whatever your particular sky is, you're not going to do it.

[B]

Yeah. And other than like a guilt that they feel like their role should be doing more of it, the thing that was actually showing up for their organization was just strategy articulation and artifacts that nobody like gave a shit about. Like everybody could tell that there's not really a deep insight to the strategy that is being espoused. And we're all very good at kind of doing the song and dance of this is the strategy and we're going to talk about it and like everybody get in line and everyone excited about it.

[A]

Yeah.

[B]

And it, the half life on the excitement for something like that is very, very short. You know, February, we're all stoked about the new strategy. By May, nobody can find the deck. And by, you know, September we're talking about next year's and with like no memory of what it was before. And I think even the, the leaders who created it, they are the best at doing the song and dance. But I think even deep down they know, like there's not an insight here and why we have to do this, but there's not really anything in this exercise that is going to help us as an organization.

[A]

I mean like preach the number of really difficult, not difficult, I would say uncomfortable conversations that I've had with leaders in a strategy session where they have made a declaration about usually about like a revenue number or a number of users for a product or whatever. And I've been like, those seem good. Why? Yeah. And they're like, because then we'll have more money. And I'm like, because bigger. But why? But why? And it's pretty rare to come across a leader who can tell you. And I'm not saying that to be critical. I'm saying it because I don't see it as part of a strategy practice. And I think it's really important. And if just growth is the whole, why, like, fine, but boo.

[B]

And also we could do that process so much faster. Like, we don't need weeks and months to like play. We could spend.

[A]

Make more.

[B]

Make more. Make more. Like we spend more.

[A]

Make more, but also spend less and do make that part bigger between them, between the top and the bottom. Yeah. And then like the lazy man's version of it. I feel like we got a decade of like, you know, change the world through. Blah, blah. And I'm like, fuck that too.

[B]

Synergistic solutions.

[A]

Change that world, please. No, you know what I mean? It was like to change the world through ride sharing. Change the world through. And it's like, oh, okay.

[B]

Like, that's the kind that masquerades as like sky work, but really is just as devoid as get bigger, more fast.

[A]

It's just as lazy. It's just like the less capitalist version. So I'm putting a fine point on this. Not to be a pain in the ass about it, but because I think it's missing because it's not asked of us and because it's really hard to do. And because when you're in the leadership seat and someone does ask you that question, I've been that person. It feels immediately like what they're asking you to do is show your math on your strategy and justify why you picked it. And that's not really what they're asking. What they're really asking is like, why this instead of something else? Like, what do we get if we do this? And that is a question worth having an answer to as a leadership team.

[B]

Yeah. And it's not the type of thing that you uncover and develop and really beat up in like 190min session.

[A]

No.

[B]

Strategy day. No.

[A]

No, it's not. No, it's not.

[B]

Yeah. Yeah.

[A]

So I feel like you're nailing like a lot of what is sunshiny about this and where the disconnect is there between like the declared aim and what it responds to. Like there's already a break there. What about further down between sort of a generic declaration and then how it actually gets executed and then how people show up to that?

[B]

Well, yeah. So what I was thinking about in the kind of the Twilight Zone Y type of stuff, basically. Like, what are our ways of working that help us actually do this better? So what has been true across all of these projects? You know, have you heard of this thing called an operating rhythm? We like them. We're a fan of them.

[A]

I haven't Tell me, tell me more.

[B]

Episodes that we've done about them. But, you know, meetings get a bad rap. But I would argue you could look at your calendar and see what your priorities are. So let's start by. By protecting some time for sky work, even if we don't know what that actually means yet.

[A]

Yeah.

[B]

And you could do a lot worse than getting your team together for every Friday for an hour and somebody brings an article and we talk about it. Somebody shares a video and we talk about it. I don't care. But basically it's spend that time doing anything except the tactical stuff that you spend most of your time thinking about. And build a rhythm of raising your gaze up to the sky. Making sense of what you are seeing there as a team is a good starting point, at least.

[A]

I love that. I also think that while you're busy changing your operating rhythm, like, really schedule time to talk to people that don't work at your company.

[B]

Yeah.

[A]

You know, it's like really easy to get into an echo chamber. That is true of every company I've ever worked in or around. And I generally find that, like, I ask people questions that I'm having a hard time answering and like, everyone will give you their opinion. And so I just ask people shit all the time. All the time. And, you know, over time I've found like, the people whose opinions I feel like are the most applicable to our organization and our work. So I just bug them the most. But it's not happenstance. It's like I have my own metric for how many of those conversations that I have in a month. And I do consider it part of my job, not like an ancillary thing that may or may not happen.

[B]

Yeah. What I love about this topic in this part of depth finding as kind of a individualist, by just inclination, there's a lot of individual habits that you can develop here that really can go a long way. So doing what you just described, carving out an actual reading and thinking time, having a journaling practice where you are like, writing down your thoughts about what is actually happening. You're maybe making predictions in writing and then going back and checking them over time. Like, there's so much to be done as an individual where you don't need the buy in of literally anybody else to really level up your ability to interact with the sky.

[A]

Yeah. You know what I just realized also? I feel like in a lot of transformations that I've been part of, where there is a sky motivator, there's like one or a couple of leaders who are really locked in on it and are sort of dragging the organization's attention toward it. And I feel like they're doing the work that you're talking about, but they're missing the routine, the Twilight Zone routines where like we all see the problem together and we all agree that this is the next evolution for us because obviously this is the meteor that's coming toward us. And this doesn't just like, like to the earlier conversation, not just the leadership team. Like, if you're a product team inside of an organization that's making apps for the employees, your sky is the workforce and they're changing needs. But like, there is a little bit of a one, two punch of individual consumption and reflection and opinion formation and then enough synthesis and coherence that it doesn't feel like I'm the only one who's going like, look over here, look over here, it's coming. Look over here. Because like, that's exhausting. And you'll never get the kind of momentum the way that you do when a group of people is in conversation with the external environment and has agreed on what they are sensing and how they want to respond.

[B]

Totally. So just a couple of things kind of in that more Midnight zone layer.

[A]

Yeah.

[B]

So what is going on? I mean, I think sometimes people just aren't curious and you can really dig into like why that is. Maybe people would be curious if they had the time and the support to like actually follow that curiosity. Maybe they've been smacked on the nose too many times for being curious. There are os kind of things going on that are keeping them from that curiosity. But that is definitely present in the midnight zone for folks when we talk about this. I think a really powerful one is just the importance of self conceptualizing yourself as a. I put it in quotes, but a strategist, like, it is part of your job and your role, even if it seems very far away from where the strategy is happening. To be thinking like a strategist, to be understanding and hypothesizing about, because things like this are happening in the external environment. That's showing up for us internally like this. And here's what I think about it, and here's what I think is going to happen I think you can begin to self identify in that way without making any grand pronouncements or really changing that much about what you're doing. But just starting to care about or think about this as part of what your role requires, I think is an important step in that.

[A]

In this direction totally. And like, if what Sam just said makes, like, your palms a little bit sweaty, like, this has never been easier than it is in this moment. Because, you know, obviously, like, full disclaimer, like, check your privacy settings. Don't get fired. Disclaimer over. When I am doing this work, which I do all the time, I'm like, this is my Persona, this is my company. This is what we do. This is the type of client organization that we work with. What should I be paying attention to? Like, set aside an hour to have that conversation with ChatGPT and I guarantee you will come away with insights and it will not be a heavy lift. Now from there, you do have to develop your own sense of, like, taste for what lead to follow and curiosity to do so. But it's not like you have to start with like a blank Google box anymore or somebody being like, look over here. Now you can get personalized curated sky information anytime you want to in a conversation with an expert that understands the entire Internet. Like, nobody has an excuse anymore.

[B]

No, not at all. I think we got a lot of juice out of essentially an anti example.

[A]

It was an anti example, but we were still able to talk about all the things we wanted to.

[B]

An actual example, maybe.

[A]

Maybe an actual example. Yeah. So we have some really interesting ones from client organizations. But because a lot of them also don't have yet, they don't have the moves yet that I think they should be making, I'm going to talk about the ready instead, actually. Because, you know, the thing is, folks, you all probably know this from listening. Like, the way that we work at the ready is always going to be edgier than what our clients are going to do. And that is by design. And it's the nature of the beast. Like, we just have freedom at our size and in our structure that most orgs don't. So I give you these examples not because client examples aren't interesting, but because they're not as extreme. And I think there's more inspo. And I can also just talk about anything I want to talk about related to the ready, which obviously we can't do with our client stuff. So the big shift at the ready, like what we've been paying attention to and what I've really watched for a couple of years, not alone at all, but with other people. And we have hundreds if not thousands of data points from competitors adjacent industries. I've talked to several friends who are investors in future of Work tech about this from our clients is like the appetite for ways of working as the thing has really waned. Despite the efficacy, despite the direct correlation between dollars, efficiency, engagement, et cetera and ways of working. Mostly clients don't have the patience and the fortitude to stick with it enough to actually shift their OS without a forcing function from the sky and a declaration in the sunshine zone. They just don't. And that to me in some ways didn't always feel intuitive. Like what felt intuitive to me was like what you said earlier, which is like people know work is fucked. People know that old ways of working aren't serving. All of the data backs up that this is like a multi trillion dollar problem, bureaucracy or debt slash. Like people keep writing books about the problem and that's sort of where it stops. And so like intuitively the sky is showing that this is in fact a giant threat. It's not sufficient, like it is not a sufficient force to organize a business around frankly. And so just like over a couple of years and paying a lot of attention to how work has gotten done and what client projects have had the biggest, biggest impact and repeat customers and things like that. We absolutely still believe in and deploy all of the things that we always have. But now the aim is very much at a specific, usually cross functional, not always, usually cross functional problem that is declared in the sunshine zone. And making this shift has really required us to like think differently about who we listen to and have different kinds of advisors. And I'm paying a lot more attention now to people who aren't so like wonky in the self management space. And we are carving out a third thing that's not self management stuff and is not trad consulting the way that like a big consultancy quote unquote does organizational design and is a third thing. And that has required different aims, different sources, different conversations. Our twilight zone work now about 50% of our operating rhythm is external facing and 50% is internal looking for this very reason. And we've created a lot of practices like some have been org wide like we worked on like critical uncertainties together. That's a liberating structure. At retreat we recently did like a likelihood and likeability matrix of all of the things that we think are coming. We've done red teaming like to start really thinking about what business would eat Ours, like, it's just starting to notice based on a lot of data where the category is moving, whether that's the category we want to be in, whether we want to create our own category and what the OS needs to be for us to do that. And like, that's really fucking hard work. I don't want to say that it is easy or that it is perfect, or that we are nailing it, because none of that would be true. But I think this is how you do it.

[B]

Yeah, I mean, I. I think so too. And a observation that I was going to share is that so we have the source team, which you are obviously a part of, doing a lot of this work, but it is not happening exclusively within source. And I think that is the right way to go about doing it. Like having some folks who are really, really focused on it, but also everybody having a shared accountability to also be noticing these trends and talking about it and showing up to invited spaces to share those observations and thoughts with the people who are really pushing a lot of this work forward. It feels very fluid, even though there is a smaller concentrated group where more of that work is happening.

[A]

I mean, that's a really good way of thinking about it. Like, you have to have some people who have the capacity like in the day to actually get after this. It can't be everybody's job or it's nobody's job like anything. But to your point, I consider our existing client projects and the transformers delivering them part of my sky.

[B]

Yeah.

[A]

So like when I am forming these opinions, some of it is from external advisors, some of it's from reading, some of it's from my past clients, some of it's from prospects. A bunch of it though is like crowdsourced from the ready to be. Like, what are you seeing? And you see how many projects now are related to OP model. That's just because of this kind of sensing work that has happened internally and the way things have shifted. And so I say that because I think you're exactly right. And I think anyone who has sky work as part of their role, and I think probably the more responsibility you have for strategy, the more time you need to be spending on this. A really significant input is our members who are delivering our business. And I do think of it as like, like three vectors that I am always paying attention to. I'm paying attention to external content and advisors, I'm paying attention to actual clients and customers, and then I'm paying attention to what our own workforce says. And between those three sensors, you get A pretty interesting bunch of data to braid together.

[B]

Yeah. And then what do you do with that data? Then like, what do you. How do you start to make sense of it and make decisions about it and like actually do things in the sunshine and twilight zone with that?

[A]

Well, it's interesting because to me, and I'm curious if you see this differently. I actually don't think that most sky practices, whether you're doing future scenario planning or you're doing red teaming, or you're doing sense making or you're talking about an article that you all. Whatever the thing is, I don't think it's super wise to actually rush to planning around it.

[B]

Yeah.

[A]

So if you think about the work that we did around critical uncertainties at Retreat, which was an org wide exercise that we spent a lot of time on, Jack can link to critical uncertainties, liberating structure. It's great. If you haven't done work like this before, it's a really easy place to start and you can do it with a lot, a lot of people. And then we worked on crafting some possible scenarios and then from there the expectation is like, people will reflect on those, use them to steer. I've probably looked back on them or ported them into every sky meeting that I've been part of since and I've seen them show up in that way. But what we're not trying to do is go like, okay, well that scenario is the one. So what does that mean for the Gantt chart?

[B]

Right. Everybody line up behind this one scenario we decided, we voted on. This is the one that's going to happen. So we're going to do it. No. And say Monday. Much more amorphous kind of ambient type thing, which I think a culture like ours can handle.

[A]

Yeah.

[B]

Because we, I think we've done a pretty good job of trying to root out kind of false urgency in places where we don't need to have it. Whereas I think in a lot of our clients there is an expectation that if we're gonna do the absolute arm wrestle to get a group of people into a room for half a day, we're sure as gonna turn that output into something as soon as possible. Otherwise what are we actually doing? And I mean I, I have found myself kind of like getting into that with, with clients in terms of like, yeah, you're right. Like, all right, we did a thing. We got to like make sure like we can prove like a show, like we, it was worth our while. We had to like really advocate for this. But sometimes, especially in this type of work, it is more of a slow burn. It is a, we're making a stew here, not making an omelette. And you know, I would say both are delicious, which is breaking down my metaphor. But we want stew in this. We want to develop those flavors.

[A]

Both are delicious, but only one is fast.

[B]

That's true.

[A]

And honestly, like I also come out of sky meetings sometimes like with my own little small type A voice being like, but where are the next actions? Should this be in a board somewhere? You know? And it's like, if you need to do that, fine. But like I prefer the practice of at the end of one of these times together as a team or even with clients holding a little bit of time for individual reflection rather than like spinning up a bunch of shit to do that may or may not move the needle. I will tell you that in the arc of the last year, what this sense making and sky practice has resulted in is a new essential intent and all of depth finding. Yeah, but what it wasn't was like, we need a new icp, we need a new framework. Somebody go make one. Like it just. I just don't think that's how it goes.

[B]

Yeah, I think you are right and I think you're putting your finger on kind of some of the Midnight Zone stuff. Those little voices that either need to be quieted or on the positive side, like encouraged, like I. There are, there are the positive. To our point earlier, Midnight Zone doesn't always have to be negative, even though that's where our brains go. I'm wondering like, do you have any kind of of the more positive Midnight Zone Y type stuff that has, has shown up in the redis work on Sky.

[A]

I mean, I think that the thing that's been super exciting and enlivening is first of all, once it becomes a practice that any group at any level is doing together with any consistency, it becomes much less scary and you just get much better at it. And the conversations end up being really fun. Like, I really look forward to the next sky meeting where we do this kind of conversation and where we map out possible futures for ourselves. So it's the kind of expansive and sort of creative space that I think anyone operating in an environment today should be in regularly. And I also think that I'll only speak for myself, but I bet there are a lot of people at the ready who would say they've had this experience now when an idea becomes really clear and it like just, it keeps knocking at my door and I'm ready to share it with the team that I work with most, I never have the experience now of feeling like, okay, well, now I gotta go sell this to them and I gotta try to get them excited about it. It's like, if I'm the one with the articulation, and it's not always me, to be clear. Like, I'm just talking from my experience, if I'm the one in the moment with the articulation, that's like, I think it's this. They're like, yeah. And it's not because they're deferring, and it's not because they don't know any better. It's because they are coming to the same conclusion because we've been on the same exploration of what the fuck is going on out there. And then when one of us posits a guess at what the play is, the rest of us go like, yeah, that seems right.

[B]

Yeah.

[A]

And that feels like magic. That feels like a magic trick.

[B]

That's cool. I'll just kind of take it from my own perspective because it's really only. I only know my own midnight zone really well. So when I. I am really engaging well with the sky, or the multiple skies that show up in the roles that I hold, there is this sense of, like, confidence of. Of self assuredness in the actions or deliberate inaction that I am, am taking. And I think, you know, come back to something I said earlier about a sky. Practice is really about developing your senses. I think anytime you are able to sense the environment that you are in, you are able to move through it with more confidence. And that. That makes me excited to always invest a little bit more time and effort into doing the work.

[A]

Yeah, it's like, it's like echolocation. And also, for what it's worth, when personally I feel like I've been the one to articulate a bet and then there's been some rough sledding. It's really helpful to be able to anchor to all of the time spent stewing, validating in conversation with the environment, rather than being like, well, that was a whim that I had one day and now that it's wobbling, I guess it was a bad one.

[B]

Right. And that's not to say that if you do sky work, you never strike out. Like, of course you're gonna strike out. You're still gonna have those things that just don't work out. But I think the posture that you're already naturally in is one of experimentation. And you know that it was a well thought through, well supported bet, even if it didn't work out. And you probably have a long list of other bets ready to go that are now slightly better informed based on how the previous one went.

[A]

At least you know why you did it.

[B]

Yeah.

[A]

Yeah.

[B]

Which there's, there's a lot of just doing random stuff in a lot of organizations, and we just kind of go along with it, so.

[A]

That's so true.

[B]

All right, Rodney, we've been going for a while. I think we should wrap it up.

[A]

I think we should wrap it up, Sam.

[B]

All right, thank you everyone, as always, for hanging out with us for a while. Please like rate and review us on your platform of choice. And if you have a gnarly cross functional problem you'd like to hear about on this show, shoot us an email at depth finding theready.com the music for.

[A]

This series is Yagang by BGA and Coyote Radio. This show is produced by by our favorite Santa Claus, Jack Van Amberg, and engineered by Taylor Marvin. Our team at the ready makes it all happen by helping companies solve their biggest problems out there. So we can share stories with you right here. Thanks for listening.