Depthfinding: Twilight Zone - Where Work Happens

Summary

Podcast Summary: "Depthfinding: Twilight Zone – Where Work Happens"

At Work with The Ready
Hosts: Rodney Evans & Sam Spurlin
Date: February 24, 2025
Episode: Depthfinding Miniseries, Episode 4

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Overview

In this installment of their "Depthfinding" miniseries, Rodney Evans and Sam Spurlin dive deep into the "Twilight Zone"—the middle layer of organizational life where the real work happens. They unpack what the Twilight Zone is, how it manifests in organizations, and why most business problems (and solutions) play out here. Using a real-world example from a data analytics firm, they show how companies typically overlook this alive, dynamic layer in favor of superficial strategies and tangible outputs, often to their own detriment.

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Key Discussion Points & Insights

1. Personal Check-In and Tone Setting

• Rodney and Sam kick off with a playful exchange about their favorite pieces of clothing, establishing the episode's candid, human tone.
  • Rodney tells a story about her favorite leather jacket found in Kyoto, Japan (00:46).
  • Sam describes a gigantic, cozy sweater his mom knitted (02:16).

2. Twilight Zone: Origins and Metaphor

(03:01–07:59)

• Rodney shares the model’s origin: Her early-morning musings on the "Twilight Zone" as both TV show and oceanographic concept.
  • “The words Twilight Zone just felt to me like the experience of being at work and trying to, like, figure things out.” – Rodney (04:22)
• The metaphor: The “Sunshine Zone” (surface, visible layer) gets most of the attention, but “barely anything... actually lives up there;” the Twilight Zone teems with life but is less obvious (05:28–06:38).
• The Twilight Zone represents how work happens—behaviors, routines, interactions—not just what work gets done.
  • “How you deal with people's emotions, reactions, motivations, behaviors is in the Twilight Zone.” – Rodney (06:14)
• Organizations often focus on surface-level change (“Sunshine Zone”) and emotional fallout (“Midnight Zone”), skipping the “how” that actually drives outcomes.

3. The Real-World Example: Data Analytics Company

(08:33–17:26)

• Company is losing customers but doesn’t fully understand why.
• "Sky" (external force): Customers are leaving; unclear if it's competitor-driven or a shrinking need (09:25).
• "Sunshine Zone": The company responds by mandating customer proximity and hiring "grownups" to add control and professionalize processes.
  • “There’s this kind of general sense that we need some grownups in the room.” – Sam (09:54)
• Common Misstep: The reflex is to push their solution harder, hire heavy-hitting execs, and declare strategies—without understanding the true nature of the problem.
  • “The answer is almost never, just tell them why our solution is so great.” – Rodney (10:42)

4. Midnight Zone Reactions

(12:45–19:23)

• Team feels “serious sense of loss,” shame, and existential worry when outsiders are brought in.
  • “There’s a serious sense of loss and probably some resistance starting to cook up in folks who were there from the very beginning.” – Sam (13:37)
• Loss of identity, value, and belonging for original, scrappy team members.
  • “Do I still belong here? Am I still valued here? … Is all of the stuff that I was able to do to get us to this point part of the next chapter or not?” – Rodney (17:26)
• New leaders bring their own (potentially misaligned) practices, causing anxiety about rapid culture change.

5. Twilight Zone in Practice: Where Solutions Live

(21:33–40:36)

• Hiring a Leader: Tiny distinction in impact—adding a role is “Sunshine Zone,” but HOW that leader changes routines/processes = Twilight Zone (21:58).

a) Beware Superficial Mandates

• Mandating “FaceTime with customers” is common but shallow if it focuses only on activity, not impact (23:08).
  • “I can go see people all the time doesn’t necessarily mean that it is going to do anything in terms of our customer acquisition or retention.” – Rodney (24:08)
• True value comes from understanding users’ real problems, not showcasing your solution.
  • “The best book for this is The Mom Test. It’s such a banger…” – Rodney (25:10)

b) Metrics & Accountability

• Companies often use outcome targets as a blunt tool (“number of customer visits,” “quota of sales”).
• Critical questions: Do metrics capture learning and experimentation, or just green/yellow/red outputs?
  • “A number on a spreadsheet... does not really get into the quality of activity behind what that number is trying to describe.” – Sam (28:46)
• "Disciplined experimentation" and discussing what’s working is more useful than fixating on targets (30:03).

c) Systemic Approaches Scale

• Good Twilight Zone routines (“moves”) help everyone, not just superstars—reduce fragility and raise the bar organization-wide (32:27–34:10).
  • “Everybody’s sky is different... but Twilight Zone stuff can scale.” – Rodney (33:19)

d) Retrospectives vs. Post-Mortems

• Most companies do retroactive, unhelpful “post-mortems” (often blame-filled, Hunger Games style).
  • “The worst version... was the Hunger Games... we all got in a room and just basically ripped each other’s work apart for three hours.” – Rodney (35:12)
• Preferred method: Ongoing, cross-functional retrospectives that are centered on collective learning, not blame (37:11–39:27).
  • “You want everyone to be mad at the problem and to feel that they are bound by their desire to eliminate it.” – Rodney (39:15)

6. Designing and Sourcing Good Twilight Zone Moves

(40:36–47:03)

• Best “moves” are rarely inherited whole from other orgs—iterate, experiment, and adapt to your context.
  • “Inherited Twilight Zone moves don’t tend to be great.” – Rodney (41:05)
• Use outside resources as inspiration (books, podcasts, Liberating Structures, even AI tools). Context matters; don’t copy-paste.
  • “Don’t read a book about Netflix and be like... we’re just gonna take that and we’re gonna install it here.” – Sam (43:01)
• Good moves are elegant, simple, and people-positive; avoid complicated, punitive, or mistrustful routines.
  • “If it’s overly complicated, it’s bad... complicated vs complex, we’ve been to that rodeo. But... the best Twilight moves are elegant solutions.” – Rodney (45:49)
  • “If it doesn’t feel people-positive, I wouldn’t start there.” – Rodney (46:12)
• The only way to really know if a move works is to try it, experiment, and retrospect (44:44).

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Memorable Quotes & Moments

• “This is where you fix shit: here.” – Rodney, passionately summing up the Twilight Zone's importance (34:47)
• “Twilight Zone moves elevate everybody.” – Sam (32:27)
• “You want everyone to be mad at the problem and to feel that they are bound by their desire to eliminate it.” – Rodney (39:15)
• “Don’t read a book about Netflix and be like... now we are the Netflix of potato delivery or whatever the company is.” – Sam, humorously (43:01)
• “If it’s overly complicated, it’s bad.” – Rodney (45:49)

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Timestamps of Key Segments

• 00:46 – Rodney’s leather jacket story
• 02:16 – Sam’s giant sweater from his mom
• 04:22–06:14 – Origins and oceanography metaphor of “Twilight Zone”
• 09:25–12:45 – The real-world example: data analytics company
• 13:37 – Midnight Zone reactions: loss, shame, change anxiety
• 17:26 – Belonging and identity during organizational shifts
• 21:33 – What’s Sunshine vs. Twilight in hiring moves
• 25:10 – The right way to “stay close to the customer” (The Mom Test)
• 28:46–30:40 – Why metrics aren’t enough; experimentation matters
• 32:27–34:10 – Twilight Zone routines as scalable infrastructure
• 35:12–36:49 – Post-mortems vs. retros: what actually helps?
• 40:36–44:44 – Sourcing and designing new Twilight Zone moves
• 45:49–46:12 – Traits of good Twilight Zone moves

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Recap & Takeaways

• The Twilight Zone is where real organizational change happens. Surface-level declarations and emotional management aren’t enough.
• Good Twilight Zone “moves” are practical, systemic ways of working—routines, principles, experiments—that shape how work gets done every day.
• Effective organizations consistently attend to these practical routines and adapt them as contexts change.
• Elegant, people-positive, and experiment-driven approaches trump inherited or overly complicated routines.
• Retrospectives should be frequent, cross-functional, and learning-focused.

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For Listeners

• If your team or company seems stuck, pay more attention to the “how” beneath the surface.
• Start small: experiment with Twilight Zone routines, reflect, and adapt.
• Find inspiration, but always contextualize and co-create with your team.

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(For inquiries or gnarly cross-functional challenges, write to [e-mail].)

Transcript

[A]

Hey, everybody. Welcome back to the show. I'm Rodney Evans, and that guy with the sweater that we're going to talk about in a minute, very excited. Is Sam Sperlin.

[B]

Hello, Rodney.

[A]

Hello, Sam. Welcome to our podcast. It's called Outwork with the Ready. It's a podcast about modernizing organizations so that they are future ready.

[B]

This is the fourth episode of our miniseries on depth finding. Did you know that, Rodney?

[A]

I did not. Thank you for clarifying.

[B]

I know you do.

[A]

Okay, well, I'm ready to dive in. But first we will check in with a question from Sam. What you got, Rodney?

[B]

What is a favorite piece of clothing you own? And why not? Why do you own it? But why is it your favorite?

[A]

I'm like, I bought it. I didn't steal it from a store. I really love clothes. So this is a hard question because I feel very attached to most of the garments in my closet, but at present, I am really quite a obsessed with a leather jacket that I bought. Right around this time last year, I was in Japan for the holidays, and I really wanted to buy a leather jacket. And I looked in some of the stores that I knew would likely have one in Tokyo, and I didn't find anything. And then we were in Kyoto, which was the third city on our stop. Ed and I were in a food market. I went to find the public bathrooms, and I stumbled onto a store full of leather jackets. And there was this one leather jacket, and it is a Korean hunting jacket. It has, like, a pheasant pocket in the back. It fit me. And I'm texting Ed, being like, I'm not coming back. I'm trying on every jacket in this store, and I just feel like it's very cool. Like, whenever I wear it, I'm just like, this is a fucking cool jacket. It's also very warm, and I just love it. I love it so much.

[B]

That's a great story. Does it make you want to kill pheasants?

[A]

It doesn't. Surprisingly, no. It has not raised any kind of bloodlust in me that wasn't already there. Sam, I feel like I know what your favorite piece of clothing is, but I now I really want you to fully describe it.

[B]

I don't generally care about clothes at all. However, a couple years ago, my mom knit me this sweater that I'm currently wearing, and we were joking before we started recording. It is very large. It is like my mother has never met me, and she knit me a sweater. But it's very cozy. It's very soft. I like to think it is somewhat fashion forward because it is so huge. Like, I think it's a deliberate fashion choice and I just roll with it sometimes.

[A]

And that is what kids are wearing.

[B]

Episode of the podcast. Wearing my podcast blouse.

[A]

Okay. Yeah, well, sure. I mean, we want a little bit of variety in those thumbnails. Yeah, it looks very cozy. Shout out to Mrs. Sperlin.

[B]

Thanks, Mom.

[A]

So today, Sam, we are cruising through our death finding miniseries. Today we're going to focus on the Twilight Zone, which is like kind of the readiest bread and butter. We're like a Twilight Zone fam here. So I think it's going to be our job today to talk about something different that people haven't heard 900 times on this podcast, which we plan to do. And also like, really how to conceive of the Twilight Zone in relationship to the other levels, because you have 200 other episodes of this show to just tell you about practices you could try in the Twilight Zone.

[B]

Yeah, yeah, that was the tough thing sitting down to like plan this in some ways. I just thought we could record like a three minute episode and be like, watch or listen to all other episodes of this podcast for lots of Twilight Zone moves. So not going to do that. Because I do think the depth finding framework has given us new ways to think about some of our old moves or why the things that we worked on that worked really well, why they work, why the things we've tried that don't work, don't really work. So I'm actually excited to dig into all of our tried and true Twilight Zone moves in a new way.

[A]

Awesome.

[B]

All right, Ronnie, I think a good place to start is with a little bit more information on the origin story of this model. Because I'm pretty sure it started with the Twilight Zone for you. Is that right?

[A]

Yeah, it did. So one morning when I was like half awake in my living room at 5am trying to write a book before my day job, I thought about that old TV show the Twilight Zone. And I don't remember actually what happened on that show, but. But the words Twilight Zone just felt to me like the experience of being at work and trying to like, figure things out. How it's sort of like your existence in like a team is sort of like this little place that feels different than all of the other places or the surrounding rapper or whatever. And how like you can make your own rules in this place that feels like a protected space. And then I googled it. Cause I was like, what was that show about? Was it about aliens? I don't remember. And what I found was that Twilight Zone is actually a term that's oceanographic that describes this depth of the ocean that is murky and this idea that some light reaches it, but it's not actually clear and transparent. And most importantly to me that the Twilight Zone is absolutely like teeming with life. And I just thought what an interesting metaphor. That the Sunshine Zone is this really visible superficial layer that gets most of organizations time and attention and resources. Barely anything in the ocean actually lives up there. And then there's this whole massive depth that you can't really get a handle on what's happening, but it's just like full of stuff happening. And I was like, that feels. Feels like my experience at work. But then of course like got curious about the other depths. And then eventually it turned into a whole ass thing. So the Twilight Zone, we think of this as the how of all the zones, really how you deal with people's emotions, reactions, motivations, behaviors is in the Twilight Zone. How you sense the external environment and do skywork is in the Twilight Zone. How you steer and set strategy is in the Twilight Zone. So like the content of all of it lives in the other zones, but the how you do it lives in this depth that I don't really see articulated in other places. Which I think is why it was very compelling to me.

[B]

Totally. The part that I really love is that idea that it's teeming with life in a real ocean. Because in an organization that is where all of the activity actually is happening. Whether it is only like non. Like we haven't defined anything in the Twilight Zone. So we're just making up and people are doing what they're doing. Or do we have a better defined Twilight Zone with some specific moves that are actually grounded in things going on in the Midnight Zone and in support of aims in the Sunshine Zone and informed by what's going on in the sky. There's just so much there. And I think the proof is, you know, the ready has been around for a long time doing predominantly Twilight Zone work with organizations. Like, there's a lot of meat on that bone.

[A]

There is so much meat on that bone. And like, if I think about when I had jobs in regular companies and it's similar with our clients now, it's just like how little consideration is given to those routines and those ways of working. And it is the most alive part of the organization and. And it gets like the least attention. Like the focus in so many organizations is just the Sunshine Zone and then dealing with the reactions in the Midnight Zone and just like skipping over the most important part, which is like the how is everything?

[B]

Yeah. So I kind of already alluded to it. I think this is going to be a tough episode because I'll speak for myself. I'm going to be tempted to just kind of give example after example of, like, Twilight Zone things people should do, algorithm adapt, strategy, like all the. All the greatest hits that we love. But we want this to be more than just that. And maybe we should start with a. Like we have with the other episodes, like an example that we can kind of hang the specifics off of while exploring, like, how Twilight Zone stuff actually works, where it comes from, how to do it well, that sort of thing.

[A]

So we have an example from a data analytics company that we thought was a good one for this. Because the focus of a lot of the Twilight Zone moves here aren't all, like, ready defaults. There are a lot of things that we do and do with clients, but they're not as many things that we've talked about on this show. So we thought it would be a fun one. So I'm going to start from the top and I'll talk about the sky and then maybe you talk about the Sunshine Zone and then we'll dig into the Twilight Zone. Yeah, sure. Okay, cool. So basically, the presenting external force that this company is responding to is that they just have customers leaving. And there's a category of customers leaving for competitors, and there's a category of customers that are just like, no longer buying what they're selling. And so the sky trend is like, customers are leaving and that is a problem.

[B]

I'm not sure that they know for sure, like, how many are in each bucket. They know just the customers are leaving. They don't necessarily know are they going to other competitors? Are they just no longer needing this? So there's. There's actually probably work to be done for them to figure out what is actually going on in their sky. See previous episode about the sky A hundred percent.

[A]

And so, Sam, what are they doing in the Sunshine Zone in response to this general panic that customers are piecing out?

[B]

Yes. So a couple of things. One, they have this kind of blanket mandate to stay close to the customer. Like, we know customers are leaving. Like, we gotta figure out why they're leaving. Stay close to them. Or, you know, if you have an active customer, stay close so they don't leave. Basically, there's also this kind of general sense that we need some grownups in the room. We need like Adult supervision. We're. We're no longer a scrappy startup. We need some control in here. So it's the introduction of various policies and processes, and then there's just this declared strategy in the Sunshine Zone to sell customers based on roi. So they're just really focused on, like, we have this solution and we have to get people to buy it. So it is written down. We have a strategy like, let's go make it happen.

[A]

Totally. And I feel like this is super common. And something that I have learned a lot about over the last 18 months is, like, when you see customer churn, whether you're running an internal function or whether you're trying to bring a product to market, the answer is almost never. Just tell them why our solution is so great. So it's like, on the one hand, I completely understand the instinct that's like, people are leaving. Tell them why they shouldn't go. It's just like, please stay at my party. There's an open bar. But actually, what a better and more interesting and more nuanced take on this is, like, are they leaving the party because they don't have a babysitter at home? Are they leaving because there's a storm blowing in? Are they leaving because the party sucked? Like, the move here is actually not push solution and hire grownups to do a better job pushing solution. So, like saying in the Sunshine Zone that that is the answer is very unlikely to get you the result that you're after in terms of customer retention or new customer acquisition.

[B]

Yeah. It cuts off potential nuance in favor of, like, oh, we have the answer. No, like, we just have to do the thing. And it's easy to forget or ignore that by selecting the thing that we're going to do. We have basically said everything else is not impacting the situation, which you got to be damn sure if you're going to come down that hard.

[A]

When we see problems like this at the upper depths, there's so often something going on where, like, the world is changing faster than the organization and the org just can't keep up. And so in this case, it's like, there's something that's changed in the customer landscape because there was a time that they were full up on customers. Now they're not. And so really understanding those externalities, even over just being like, we're pretty sure we've got a solution. People just are not aware of it, is the move.

[B]

Yeah. What do you think about hitting Midnight Zone real quick so then we can, like, coming back and just do Twilight.

[A]

I love that idea.

[B]

Bring it all together. Because I think the segue to Midnight Zone is actually on that. That kind of the hiring corporate leaders, grown ups, adult supervision, sort of Sunshine Zone move that this organization is making has got to be bringing up some serious Midnight Zone stuff for people.

[A]

Is this the hand gesture we're gonna make for the Midnight Zone?

[B]

Midnight Zone stuff?

[A]

It's near your down there. It's just like, yeah, I love that.

[B]

Weird little animals with lots of legs and kind of jellyfishy just going like this and getting on you.

[A]

You're just never gonna let the Sea Beasts go.

[B]

I've done a remarkable job of not talking about Sea Beasts for four episodes. Give me these little guys.

[A]

It's fair. You can have the little guys. They're like sea anemones.

[B]

Thank you. And what I mean by that, as someone who has been at an organization from the very early days, if you feel like you remember a previous time where we were scrappy, we were solving problems, maybe we didn't have this presenting problem that we have, right? And now the answer to it is, well, we were doing it wrong back then and we, we know better now and now we've got some real adults in the room to kind of figure it out for us. Like, there's a serious sense of loss and probably some resistance starting to cook up in folks who were there from the very beginning.

[A]

I think that's really smart. It also, you know, hiring a heavy hitter to solve the problem. It might assume that there's something wrong with the organization rather than something different about the market. Not necessarily, but a lot of times, like I've seen that play a lot where they're like, we're going to just bring this executive in and like they're going to like clean house. Like they're going to really get this organization humming. And what often is not taken into account is like, well, you know, there's other stuff that's happened externally. It's not just that all the people here like suck and they can't make it to the next sort of evolution of this organization. So like when the adult supervision is hired, what are some of the things that you think come up for people? What are some of the midnight zoning reactions?

[B]

So I think there's, you know, nervousness, worry, resentment. But I think one that didn't come to mind for me right away, but once it landed on my head, it seemed, landed on my head, landed in my mind, it seemed very shame. Like, like we couldn't, we couldn't figure out our Own shit. So we had to outsource it by, like, hiring a heavy hitter or adopting, like, a fundamentally new way of working that is at odds with our scrappy origins because, like, what we were doing before is no longer working. And I'm ashamed that I couldn't get us out of that or contribute to getting us out of that.

[A]

Yeah, I mean, I think that probably happens to a lot of people. There is often a feeling that what drew people to something that was scaling when it was scrappy, everybody felt like they could have their fingerprints on it and, like, their opinions really mattered and, like, they were architects of this thing that shifts. When you basically are saying, like, no, no, we're hiring a professional architect now, you all just get a hammer to build based on what they draw for you. And I would imagine that there's, like, some loss of identity in that for people who have been around and were part of the creation of it. I'm, like, projecting onto this based on a lot of things I've seen is the hard reality is I do think organizations go through these phases where the talent does have to change. And I've definitely seen firsthand examples where someone who was, like, incredibly scrappy and sort of had like, a just figure it out insurgency mindset, spin a shitload of plates and just, like, make a mess and see what happens. Like, that's so. That kind of energy is so necessary. Necessary to get something up and rolling. And having, like, a corporate executive at that point is a terrible fit. And then also, at a certain scale, that person becomes, like, a chaos agent that the system can't take anymore. And so there's, like, a lot of Midnight Zone stuff in here. When you see a company articulating a phase shift, most of which boils down to, like, do I still belong here? Am I still valued here? And is. Is all of the stuff that I was able to do to get us to this point part of the next chapter or not?

[B]

Right, right. And that's, like, some seriously heavy shit. And to think that it doesn't show up in Twilight Zone stuff or, like, how people react to Sunshine Zone things. Like, of course, that, like, dark matter antimatter of our organizations is this Midnight Zone emotional stuff that we're not necessarily there to do therapy on, folks. But we got to acknowledge that this stuff, it's a center of mass in a way that can be hard to see, but creates a lot of motion and activity that is hard to attribute to anything else.

[A]

Yeah, absolutely. And then there's other worry, I think that crops up that comes to mind for me, which is when the executive move is run, those folks come with their own Twilight Zone stuff, and they're like, this is how I run a business. And for people especially who have been part of something that scaled up, that's really scary. I mean, it's scary when you're working in an organization and somebody just takes over the function. But at least usually there's some coherence already with the culture. If it's an internal person, they're unlikely to be just, like, completely countercultural. Whereas if you bring somebody in from the outside who's like, okay, I'm going to completely make the comp structure now, like, eat what you kill, and I'm going to insist on five days in the office. That's like, real shit. That people who maybe are feeling the shame you mentioned, maybe are feeling existential questions about whether they belong there and can contribute, and then maybe are also worried that, like, their literal lifestyle and way of working and way of existing is going to, like, change on a dime. Yeah, that's, like, a lot of distraction going on because of these few Sunshine Zone declarations.

[B]

Totally.

[A]

So we've talked about, again, all of the negative emotions and reactions in the Twilight Zone, because that's what you and I do. Is there anything you think that is maybe on the more positive end in response to some of these mandates?

[B]

I think there's this potential of, like, a collective exhale and, like, someone will save us. Like we have. I mean, you said this was positive, and I will take the positive side of it first. Which is, like, hope.

[A]

Right?

[B]

Like.

[A]

Right.

[B]

Giving people a sense of hope that we have, or whether it's. We feel good about the Sunshine Zone stuff. Hopefully we have some Twilight Zone things that we're trying. Like, I have newfound hope that we can pull out of this. Um, the more negative side of that is, oh, someone will save us. I don't have to sweat it anymore.

[A]

I don't have to worry about this.

[B]

It's like, lean back and the grownups, they'll handle it. Let me just kind of keep doing my thing the way I like to do it, and I'm sure we'll be fine from here. Which is probably not the greatest energy to bring to a important kind of dire moment for an organization.

[A]

You don't want to be like, oh, Kevin's got it sick.

[B]

He's real good.

[A]

He seems like he knows what he's talking about.

[B]

Yeah, that's not even talking about Kevin's Midnight Zone stuff. If he's Perceiving, like, the organization has just put everything on Kevin. Like my dude.

[A]

I mean, I've seen that play a lot of times where it's just like, oh, here's our savior. Yeah, that almost never flies. I think that's such a good point. And look, I think if you're someone who is like resonating with this Midnight Zone that we're describing, I feel like it's very easy to hold both of those in your mind. Like when you're in a struggling organization and someone is brought in who seems to have an answer to the question, why is this so fucked up? That does feel like tremendously relieving. And if you don't want to end up not being part of the next phase shift, if you feel like you want to evolve as the organization does, you probably shouldn't just like leave it to Kevin and hope for the best.

[B]

Yeah, Kevin may be great, but yeah, that's probably not. Not a great move.

[A]

That's probably not the move. So we've sort of done this out of order, which I think was fun for the case at hand. But now let's move into the Twilight Zone, because that's the point of this episode. So the first thing I want to ask you, Sam, is how should people think about the hiring of the mature, wizened expert? What part of that is Sunshine Zone and what part of that is Twilight Zone?

[B]

Oh, interesting. So whatever that person is bringing to the organization in terms of the processes that they are going to institute, we talk about hiring a person, but really we're talking about hiring the things that they are going to do in the organization. And that's going to be the Twilight Zone stuff. So, you know, hopefully they're bringing some stuff that is going to align with what we're going to talk about here with good Twilight Zone things. And to the extent that they aren't and we over invest in some Twilight Zone stuff that isn't actually going to solve our problem, then we are probably signing ourselves up for some pain.

[A]

Yeah, yeah, that's going to be the case here. I see the Sunshine Zone aspect of a higher as. Like we added this to the org chart and it's going to solve our problems and then everything that then happens is Twilight Zone stuff.

[B]

Yeah.

[A]

The first thing that this particular leader did to get at those declared Sunshine Zone strategies was institute a mandate around facetime with customers to push the solution. What do you think about that?

[B]

That's fine. Right? I jumped in. I jumped in first. What do I. I mean, it's One of those things that at face value seems like a decent move. Right. Like we need to understand what is going on with our customers. So let's just mandate that we have FaceTime with them. It, it leaves pretty open what that FaceTime feels like and looks like and what you actually do in that FaceTime which is where the rubber actually meets the road.

[A]

Yeah. So like natural Twilight Zone move in service of the sunshine Zone, stay close to the customer is here are the number of times you need to travel to see the customer. Like hard to argue with the logic. And yet to your point, you are talking about like activity versus impact. So I can go see people all the time doesn't necessarily mean that it is going to do anything in terms of our customer acquisition or retention.

[B]

May make it worse.

[A]

They might be like stop coming here, you're bothering us. I think one of the things that we all tend to get wrong here, Twilight zone wise is when we are with our customers or prospects or just people that we're trying to get market signal from, we have a real tendency to ask them to respond to our solution. Would you use it? How would you use it? How much would you pay for it? Do you like me? That's not what we should do. When we are with these people, when we want to get close to our customers. The way we do that is by getting close to their problems. I want to understand with the openest mind and the openest hand what problem a customer is trying to solve. I don't want to ask them about my data software. I want to understand what is keeping them up at night, what is their strategy, what are their cross functional issues, et cetera, et cetera, then I want to ask how they've tried to solve those problems. If they've tried to hire other people to solve those problems, if they've tried other tools to solve those problems, how that's gone. Like I want to just stay right in the problem space with them. And if this is landing with any of you and you realize that you've like really fucked this up in the past, which you know, I see you. I have to. I think the best book for this is the Mom Test. It's such a banger and it really keeps you oriented to like what is the problem they're trying to solve, not what is the solution that you're trying to get them to buy.

[B]

Yeah. And this is actually making me think about how Twilight Zone moves are often connected to each other because agree with everything you said and if your organization has no way to Use that information that you just surfaced, because we're just showing people the thing that we have made, then you're probably wasting your time. And there needs to be other Twilight Zone moves around. How do we analyze this data? What do we do with it? How do we feel about it? Actually that's more of a Midnight Zone thing, but there's other things going on there in order for this Twilight Zone move to work really well.

[A]

Totally. The one thing I'd add to what you're saying is this is where potentially by doing some real discovery with existing, with existing customers or with, you know, prospects, you might hear an opportunity that your current solution doesn't address, but could. And so many of the best product stories in history are about discovering that the problem that needed solving was different than what someone had assessed it to be, but that they could easily pivot to solve it. And so this is where like again, the flexible thinking comes into play and the ability to like collate that knowledge, tag that knowledge, use AI to find patterns in that knowledge, et cetera. Because it might be that you're able to incubate a little sprint on an adjacent opportunity or an adjacent tool. Or if you're a software company like this, maybe there's a wrapper or a feature or a customer segment that you actually could address. And then rather than trying to like grab your customers ankles and keep them from walking out the door, you could go after a different market segment because you discovered what people really wanted.

[B]

Yeah. And we lose all of this nuance and interesting ideas if all we have is basically a number on a spreadsheet that says how many times did you fly out and talk to a customer? How many times? How many zoom calls did you have in the past week? Which is easy to manage to like, oh, you're three below. What are you going to do to fix that? And we're not actually having the more difficult conversation about what are you learning? What does that mean? What are we going to do with that sort of information?

[A]

Totally. So here's the next logical Twilight Zone stuff. How execution for the Sunshine Zone declarations that have been made, it's metrics is.

[B]

Like, yeah, metrics are great.

[A]

Okay, we've got a customer acquisition or retention problem. Now the account reps have a number, they have to meet those targets are non negotiable and meeting those targets will fix our problem. And we will know that the problem is fixed when we see that those targets have been met.

[B]

That just sounds like some good old fashioned accountability to me.

[A]

Think harder, Try be Better.

[B]

Okay, I will try. I will try to be better. So similar to the previous one, a number on a spreadsheet, a target that we're trying to shoot for does not really get into the quality of activity behind what that number is trying to describe or talk about. So if we have targets that we are trying to hit, what does that actually mean? What do we actually care about? What will actually drive these numbers? Maybe we should be talking about, you know, the experiments that we are running to try to get to these numbers, because I think I've seen this over and over. And basically we have these metrics update meetings where chances are everything's green because everybody can massage metrics.

[A]

Why are we even in a meeting if they're not green?

[B]

Straight up lie. But the interesting conversation is like, Rodney, your numbers are great this week. Your outcomes are really good over the past couple of weeks. Tell me about the experiments you've been running. Like, what have you been doing differently? And maybe I can try those sorts of things. And that is a quality of conversation that is never going to be captured in a metric on a spreadsheet. And if we're only optimizing for the numbers that show up in a spreadsheet, then we're not creating the conditions where that experimentation, that learning from each other can actually happen.

[A]

Yeah.

[B]

Does that make any sense?

[A]

I think that's right. And, you know, when we talk about experimentation here, this is where, again, ways of working, like, what is the hypothesis that you're testing? The hypothesis that was tested so far is fly to Dallas and take them out to dinner. What if there's a different hypothesis which is like, have a real discovery conversation, and at the end of it, ask if there is someone else that you think I should talk to and then take that call and then see where that leads. Like, we want to have disciplined experimentation and we want the conversation to be about what we're trying and how it's working, not what the target is and whether we missed it.

[B]

Yeah, exactly. And that's not to say that there aren't metrics that are worth tracking. But of course, we need to think really carefully about leading and lagging indicators, too. Because if our metrics are predominantly just lagging indicators, like, what are we doing here? We're just, like, being really precise with feeling bad, which is like, I don't know that we necessarily need that. But leading indicators that are true, leading indicators that we can do something about, like that metrics meeting becomes a lot more fun. It becomes a lot more useful.

[A]

Yes, exactly. And I think, like, if. If we're talking about a software business, maybe a leading indicator is that someone stops logging in. Maybe a leading indicator is that their service requests go down. Maybe these are leading indicators that people are starting to disengage from the product. And that if they're not living in that product day to day, it might mean that it's because they don't need it, which might be leading to a cancellation at some point. I don't know. I'm not in this business. I'm just saying this is like the creative way that we want to start looking at both. Because to your point, Sam, if we just wait until the target is missed to be like, you suck, we should just fire you and get somebody who's better at selling this solution. We're not changing the Twilight Zone in a way that's likely to fix the problem for everyone. We can probably put a better salesperson in, and they'll probably have better Twilight Zone experiments to run. But that is a band Aid solution. Because what we're not doing is really figuring out what are the experiments that we're proving that fucking slap that we're scaling and that then we're really learning from and routinizing in the Twilight Zone. That's like. That's the essence of what I'm trying to get at here.

[B]

Yeah. And I think you're helping me coalesce around this idea that good Twilight Zone landscapes or collections of Twilight Zone moves elevate everybody.

[A]

Yeah.

[B]

You don't have to be the superstar salesperson. If you are working in an organization that has really explicit and good and useful Twilight Zone stuff that helps elevate you. There's natural distributions of talent for all sorts of things in the world. And incredibly talented people. Maybe they don't need some of the Twilight Zone stuff. But if we're building our organization such that it can only work if we get the top 0.1% in every discipline that we're doing, then, man, we're putting a lot of pressure on our hiring. And an attractive place to work that's.

[A]

So fragile because it's just like one superstar. Leaving is existential and something. When we were developing this model that Jack said to me that has really stuck with me is like, everybody's sky is different. Everybody's Sunshine Zone is different. Everybody's Midnight Zone is different. But Twilight Zone stuff can scale. Like, it can really. I know. He's so smart. Really banging habits in the Twilight Zone often can really serve across, like, multiple disciplines. And if you think about this example, we're talking about, like basically a sales conversion problem. But think about how much that we've just talked to is relevant to HR developing solutions for their internal customers. Like almost all of it.

[B]

Yeah.

[A]

And it's like, you know, I could keep going on here with this thought exercise, but my point is part of the reason that we're such believers in this as the highest leverage zone is that it's because, like, you can get to defaults that lots of different functions can use, that lots of different teams can use that kind of work every time. And are are more context agnostic. And so all of the fiddling with the Sunshine Zone and then all of the ignorance of the Midnight Zone just feels so wasteful because it's like, this is where you fix shit is here.

[B]

Love that.

[A]

I think to finish out this example, there is one more move that these folks are making in the Twilight Zone that again feels like a very logical response to the Sunshine Zone and we are going to tear apart. And that is the post mortem.

[B]

They're actually doing not the worst version of it.

[A]

Not the worst version, because the worst.

[B]

Version is Gladiator Time.

[A]

Oh, it's the Hunger Games.

[B]

Tear each other apart. Yeah.

[A]

Yeah.

[B]

Which it sounds like that's not what they're doing, but maybe too far in the other direction.

[A]

They're doing a more passive version of that. So the worst version of the postmortem, which I used to get to participate in annually and it was my least favorite day of the year, was the Hunger Games, where it was like, we finished this big process and then we all got in a room and just basically ripped each other's work apart for three hours.

[B]

Yeah.

[A]

After being in a three month process where like no one slept or saw their families. And then we would just get together and be like, here's all the ways you fucked up. And then that was it.

[B]

Here's three months of resentment that I've built up. Let me package it and give it to you.

[A]

Let me just get this out while we're here. Now that you're all like sleep deprived and borderline dissociated, let's just talk about the ways in which you've wronged me. So don't do that. The postmortem in this example, as described to us, was that it wasn't so much about blaming, but it was more about just like narrating or demonstrating effort. So the showing your mom the post mortem, in this case of like, what happened with that customer that left was more about like, well, I did fly to Texas and I did take him to dinner and we did have a great conversation. And he did say that he believed in my solution. So I. I don't know why he didn't renew, which is not as bad as it could be, but is not particularly useful in making any change to the Twilight Zone. Because what do I extract from that that's useful? Not much. So what might people do instead in this sort of category?

[B]

Yeah. So one thought is more of like an ongoing retro process. So it sounds like their postmortem happens at a point where it's too late for the thing that we are postmorteming about. It's already dead. You can retro before then, I promise. It's actually great. You can because then you come up with ideas to keep the thing from dying.

[A]

Yeah.

[B]

So instead just get into a rhythm of. We are always kind of having potentially light touch retrospective conversations about how things are going. And that's all retro is. It's just reserved time to learn from how things are going. And sometimes it looks like getting in a room for 90 minutes and sometimes it's a slack bot asking a question into a channel and we all answer it. So that's the first place that I would counsel like thinking a little bit differently about this Twilight Zone practice.

[A]

Yeah. I used to have a client that was good at being in touch with their customers in this way, but it was very driven by the customer experience team. And the truth was that the customer had a lot of touch points within the organization, but the only one who talked to them was customer experience. And I feel like maybe from a data gathering perspective, that's okay because your customer probably doesn't want to hear from 10 different people at your company. But in terms of the actual retrospective and sense making, you probably need to bring the rest of the people who touch that customer into the mix. Because if the issue wasn't customer care, customer service or troubleshooting, it was like the interface or the product itself or dealing with service or pricing. You're not going to get that from just the one to one contact. And the kind of cross functional retroing around this, I rarely see that happening.

[B]

Yeah, I think it rarely happens for two reasons. One is just the boring logistics reasons. Yeah, a bunch of people who don't normally have to interact together, scheduling time to be together, which I feel like is the more like straightforward thing to fix. The other one is when you get cross functional groups together without like careful facilitation, it turns into a battle of functions.

[A]

Yes.

[B]

It wasn't. It wasn't us. It must have been you. And that's not a great posture to be in when trying to, like, better understand a complex flow or process that didn't have the result that we were hoping for.

[A]

Yeah, you don't want that in your cross functional retro. You want everyone to be mad at the problem and to feel that they are bound by their desire to eliminate it.

[B]

Yeah. And again, coming back to how, like, Twilight Zone moves should ideally reinforce each other. Is that an organization where we already have a bunch of Twilight Zone things where we work together, cross functionally? It's easy to do that. I see you all the time. We work together all the time. We are friends or at least, like, know of each other more than just annoying emails that we send back and forth. I meant the hypothetical. And we can now work together on that. Versus we have this one Twilight Zone move where cross functionally, we come together, and the rest of the time it's all like, just in our own functions. It's putting a lot of stress on that one move to be able to, like, develop cross functional ways of working that need places to practice and develop.

[A]

Yeah. Don't just do the one thing. That was like, the postmortem that I was in. That was like, the only time of the year that we all got together. We were like, I hate you. I'll see you this time next year. And that was. That was kind of it. So, Sam, I feel like we've really, like, squeezed the juice of this example. Is there anything else about the Twilight Zone that you feel like you need to explore?

[B]

I think I just have one question just to pop us back up kind of into the meta level a little bit. I can imagine someone listening to this episode and being like, where do you get all these Twilight Zone moves? Like, yeah, they sound good. Like, but it never. I never worked somewhere where we did that, or I never would have thought of that as a thing. How would you answer that question? Like, where do good Twilight Zone moves come from?

[A]

Yeah, our podcast.

[B]

And only our podcast.

[A]

I mean, not. No, though, like, inherited Twilight Zone moves don't tend to be great. So, like, I know for myself, I invent Twilight Zone stuff all the time for clients where there's a kind of routine that they need, and I'm in charge of finding a solution for that. But if you don't have an org designer in your midst or a solution designer in your midst that does that professionally, like, truly a great place is like, use chatgpt, use liberating, structures. Use this podcast like I've used things from other places, many of which are not copy pasted but were the seed of an idea that then I turned into a full blown solution for either the ready or the client. I think as long as it feels like you are clear on what you're designing for, you are clear on what the intended outcome is and you are retrospecting whether the Twilight Zone move you're doing is getting you closer to that outcome and you're not just taking it for granted and being like, well, we have shitty staff meetings, so I guess we'll have a shitty staff meeting. Like, I think that's it.

[B]

Yeah, that makes sense to me. You know, reading business books is actually a good place to get Twilight Zone stuff too. Not because it's just like what you said, a copy and paste situation. What you have to add to the process of reading any business book is making sure that you understand the context in which they are describing this Twilight Zone move and not losing that context when you put it into your own tool belt. So yeah, don't read a book about Netflix and be like, okay, well here's Netflix's 20 main Twilight Zone moves. We're just going to take that and we're going to install it here. And now we are the Netflix of potato delivery or whatever the company is. That's. I am, I am a professional org designer and the best example of a company I could come up with.

[A]

Delivery.

[B]

Potato delivery.

[A]

Yeah, the Netflix of potato delivery. If we had merch, I would want a T shirt that said that on it very badly.

[B]

Yeah, it's a good exercise though. I feel like it's a. It's one of the ways that I develop my org design chops is to read a book about an organization, be able to see what the Twilight Zone things are. Because it's not like most books have like listed them out. Like, here are the Twilight Zone moves. Seeing them, noting what they are like, writing down the essence of what the move is, kind of what the important context is that I am pulling it from and then putting that in my toolbox, saved into a note somewhere, saved into notion, and just being aware of it the next time I am somewhat in a similar sort of context or need to solve a similar sort of problem. That is a practice that anybody with any, any job description, any title could, and I would argue should be, should 100%.

[A]

And I feel like, you know, as long as you go into that knowing that you probably need the other people who are participating to weigh in bring the Twilight Zone move you want to do as a proposal, process it using IDM, which we've taught you on the show 900 times. Don't just be like, this is how we do strategy now. Like do the work of having people's fingerprints and you know, do the change management required. But also, Sam, like if you're not a solution designer, how do you know if you're lifting from something that is good or not? Like, what's a good litmus test for a Twilight Zone move if you don't do this for a living?

[B]

Yeah, I have two maybe opposing thoughts on this. My hot take, hot take zone is that you don't know until you experiment with it is that if you're in an environment where stakes are low, there is a willingness to experiment. Maybe you don't need tons of buy in to try a thing. I don't think it's the worst thing in the world to like kind of ignore what people are saying about a thing and try it for yourself. I think there's not that many things in the world where it's like, don't try it because it's not gonna go. I mean, obviously guardrails, safety, whatever, sure, of course, lean into trying things. The other side of that, or maybe it goes with it, is doing enough of your own individual education on a topic or how something works to be able to perceive bullshit. So I mean, with AI, I can't think of a better time to quickly get yourself up to speed on the basics of almost anything. Enough to know whether or not an experiment or a move is at least worth like investigating further.

[A]

I mean, the only things I would add are like if it's overly complicated, it's bad. Because if it's too complicated, if it's a workflow that has like 30 steps and 40 roles and 20 assets and then you're not going to really be able to run an experiment. So complicated versus complex. We've been to that rodeo. But like, I would really keep in mind that to me the best Twilight moves are elegant. Like they are elegant solutions. They're not overwrought solutions that require a tremendous amount of explanation. And I mean the other one which is kind of like duh. But I would say if it doesn't feel people positive, I wouldn't start there. Like if it's a Twilight Zone move that's predicated on people being lazy and stupid, try to pick a different one. Like try to pick one that assumes that people want to contribute and are able to change and are interested in trying stuff and even if they don't show up to it exactly that way the first time, give people a little grace and believe in them a little bit that they can get there.

[B]

Totally. Yeah, I think, I think that is a great answer.

[A]

I think that's a great place for us to wrap this up.

[B]

Yep. All right, listen up everyone. You know the drill. Please like rate and review us. And if you have a gnarly cross functional problem you'd like to hear about on this show, shoot us an [e-mail].

[A]

The music for this miniseries is Yagadang by BG and Coyote Radio. Our show is produced by Jack Van Amberg, one of the bestest people on earth and any engineered by Taylor Marvin. Our team at the ready makes it all happen by helping companies solve their biggest problems out there so that we can talk about them right here with you. Thank you for listening.