24. Ask Us Anything No. 3

Summary

Podcast Summary: At Work with The Ready, Ep. 24: "Ask Us Anything No. 3"

Hosts: Rodney Evans and Sam Spurlin
Release Date: November 25, 2024
Theme:
A robust and candid Ask Us Anything (AUA) episode where Rodney and Sam tackle challenging, graduate-level listener questions about the realities of modern organizational work, from self-management to prioritization and the pain of letting go of old projects. Listeners submitted especially nuanced and "gnarly" workplace questions, prompting deep dives into topics the hosts usually explore over full episodes.

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Main Theme & Purpose

This episode of At Work with The Ready departs from the usual "organizational pattern pull-apart." Instead, Rodney and Sam answer a series of complex listener questions about modern work, organizational structures, capacity planning, and the psychology of teams navigating uncertainty, alignment, and prioritization. The answers are pragmatic, human, and peppered with lived experience and actionable advice.

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Key Discussion Points & Insights

1. Self-Managing Teams: Structure vs. Chaos

(06:00–13:02)

• Listener Question: Does "hire smart people and get out of their way" work? Reflection on Google’s approach and the downside of under-management.
• Rodney: Emergence alone is chaos. Self-managing teams need structure for coherence; otherwise, brilliant but unfocused (Rube Goldberg-esque) work results.
  • "Emergence alone is chaos... you are very unlikely to get great results with very fragmented effort." (07:10)
  • Great strategies and teams can self-organize, but not without anchor points: clear missions, group accountability, and embedded practices.
• Sam: Leadership does not have to be centralized—even in self-management, someone can bring structure, but mature self-managing teams share leadership as a verb, not a title.
  • Self-management and leadership aren’t ends of a spectrum; teams can and must create their own clarity.
• Practical Takeaway: Before adding hierarchical roles, identify what ways of working are missing that you’re trying to paper over.

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2. Project Capacity Planning in People-Positive Organizations

(13:15–22:16)

• Listener Question: How to plan project capacity without defaulting to hard metrics in an org shifting from cost center to profit center?
• Rodney: Start with design principles: What are you optimizing for? (Clearing a backlog, quality, speed, etc.) Audit current state—what are people actually spending time on?—before prescribing new workflows.
  • "Get to a shared picture of the current state before you develop the methodology..." (17:26)
• Sam: Be skeptical of chasing hard numbers at first. Talk to people, gather stories, and use qualitative assessment before measurement.
  • Prefer "pull" over "push" systems—let people pick up work as capacity allows, rather than assigning more until “full.”
• Together: Backlog grooming should be ruthless—if a dormant project hasn’t caused pain, it’s safe to let it go.
  • "If they're really good and really necessary, they'll come back up." (21:17)
• Tools/Practices: Two-week calendar audits, prioritization frameworks, retrospection.

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3. Divergent/Convergent Thinking & The Myth of Alignment

(22:16–31:29)

• Listener Question: Why do traditional orgs rush to convergence during annual planning? Why the obsession with “alignment”?
• Rodney (hot take): “I hate the word alignment.” It’s a fuzzy, undefined term often masquerading as consensus or surrender.
  • "What does ‘alignment’ mean? Does it mean we agree? That we're all doing it? Or just that we'll stop arguing?" (23:37)
• Sam: Organizations crave certainty—converging early feels safer—but creative, effective strategies emerge from lingering in divergence and conflict.
  • "I think what alignment tends to mean is we’re done arguing." (24:29)
• Rodney: Best strategies are typically counterintuitive and only emerge if teams listen deeply to edgy, divergent voices and allow for real, sometimes uncomfortable, debate.
  • Memorable anecdote: At a tech company, the unexpected input from a VP completely redirected product strategy, because the team lingered in divergence.
• Key Insight: Strategy must be cross-functional. Stovepiped plans (e.g., marketers planning only with marketers) produce shallow outcomes.

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4. Zombie Initiatives and Internal Prioritization

(31:32–46:03)

• Listener Observation: Easy to start new projects, but internal work always loses out to revenue work—leading to “zombie” (abandoned) initiatives and frustration.
• Sam: Anything treated as “side of desk” will always be deprioritized in a service business. If you want internal work to matter, it must be structurally equal to client work.
• Rodney: The Ready has improved by using "explore teams" (small, time-boxed groups that validate a real problem exists) before launching bigger mission teams or investing heavily.
• Experiments & Emotional Responses: Both hosts share stories about launching experimental teams. Outcomes sometimes produce no direct ROI, but can be valuable for disproving false assumptions, learning, and forming relationships.
  • "If you do this correctly from an org design perspective, some of them are meant to fail..." (40:50)
  • Even “failed” explores are often successful if they save future energy/investment.
• Advice: Always do a time-limited exploration before spinning up a full project team. Accept that we are more likely to disappoint each other than clients; redesign roles to avoid dual accountability if you really want to prioritize internal work.

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Notable Quotes & Memorable Moments

• On self-management vs. leadership:
  "Leadership and self management are not separate ends of a continuum...there’s definitely a more mature version of self management that's not separated from leadership." — Sam (08:25)
• The paradox of alignment:
  "I hate the word alignment...what does it mean? Does it mean we agree? Does it mean we’re doing it? Does it mean we support it? Nobody knows." — Rodney (23:37) "What alignment tends to mean is we’re done arguing." — Sam (24:29)
• On prioritizing & pruning the backlog:
  "If it's decayed on a backlog for six months and the absence of doing that work hasn’t caused any problems, it is safe to kill that item for now..." — Rodney (21:17)
• When experiments ‘fail’:
  "There are a lot of companies who would hear what you just said and say that was a failed experiment. It was an incredibly successful exploration because we got very useful information." — Rodney (37:12)
• The reality of internal initiatives:
  "Anything that is felt and resourced...as side of desk work will always be dropped in favor of the stuff that keeps the lights on." — Sam (32:58) "We are generally much more equipped to disappoint each other than we are our clients. You’re always going to tell your home team to fuck off before you tell your client." — Rodney (45:01)

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Timestamps for Key Segments

• Traditions & Rituals Icebreaker: 01:38–03:51
• Self-management boundaries: 06:03–13:02
• Capacity Planning Without Command & Control: 13:09–22:16
• Divergent/Convergent thinking & Alignment: 22:16–31:29
• Internal Zombie Initiatives & Explore Teams: 31:32–46:03

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Tone & Style

The episode is conversational, witty, and self-reflective, blending professional insight with playful banter and honesty about successes and failures. Rodney and Sam are transparent about The Ready's learning process, making their advice deeply relatable.

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For Further Listening

• Past episodes on mission-based teams, backlog grooming, and cultural alignment (suggested by hosts for deeper dives into referenced concepts).

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Closing Note

This AUA episode is a goldmine of pragmatic advice for organizations striving to modernize work without losing sight of human complexity—and for anyone tired of hearing “alignment” without substance.

Transcript

[A]

You can't do a marketing strategy that is purely full of marketers. Just have some token invitation of other functions, like I. You get into a unhelpful, unhealthy pattern if that is how strategy is developed and kind of rolled out in a very large organization.

[B]

Hey, everybody. Welcome back to the show. I'm Rodney Evans, and that guy in the beautiful blue top is Sam Sperlin.

[A]

Does it make my eyes pop?

[B]

It's really hard for me to see in here, but I'm sure that it does.

[A]

It absolutely does.

[B]

Did Emily pick your shirt out?

[A]

She may have had a role.

[B]

Yeah. That tracks. Well done. Welcome to At Work with the Ready. This is a podcast about modernizing organizations as the future of work meets the present moment.

[A]

Each episode we turn our attention to one common organizational pattern that we think is worth digging into. We pull it apart like pomegranate to enjoy the sweet arils within and propose solutions for what to do instead. Yes. Thank you to the listener who submitted that pull apart and taught me the word aril.

[B]

It just gets weirder every episode.

[A]

Oh, and also, we're not doing that this week because it's an aua, but I just wanted to.

[B]

Yeah, we're not pulling anything. Well, we're going to pull lots of little pomegranates apart. Small pomegranates, tiny pomegranates. This week, we are going to do an ask us anything, which Sam and I love very much. And you guys asked us great questions, hard questions, gnarly questions, questions that actually required preparation and not us just showing up and saying whatever came to mind. So thank you for that, and we will try to do a good job for you. But before we do, let us check in.

[A]

Ronnie, quick check in question for you today. What is a tradition or ritual you really enjoy?

[B]

Ooh. On Christmas Day, my mom and I go to a movie and eat Chinese food. And. And I love it very much because it's so fun. But also, the ritual happened in a very funny way, which is that when we moved to the Northeast from the Midwest, we didn't know that things weren't open on Christmas day, because in the Midwest, the big night is Christmas Eve because we're like, Norwegian. And so you have presents, and the big feast is Christmas Eve, and then Christmas Day is, like, not really much of a thing. So you go out to a restaurant. So we moved to Connecticut. We did our typical Christmas Eve hurrah. And then on Christmas Day, everything was closed. And we were like, what is this place? And the only place that was open was a Chinese restaurant and the movie theater. So we went there, and then it became a thing where, like, we save up a blockbuster movie that we are super excited about, and we commit to not seeing it without each other. And then we go and do that, and it's very fun. And then I married into a Jewish family, and it squares very nice with their holiday tradition, so. So it all came together for us.

[A]

So delightful, so wholesome.

[B]

What about you?

[A]

Always words that I associate with you 100% of the time.

[B]

I was going to talk about moon rituals, but I was like, that might not be for this audience. We'll save that for another time. We'll save what I do in the woods for another episode.

[A]

My answer is this annual brothers trip that I do with all my brothers.

[B]

Oh, Boy Soup.

[A]

There's five of us. Oh, God, there's five of us. And we're kind of scattered about, kind of a critical mass in Michigan. So we find an Airbnb that's roughly halfway, and we just hang out for a weekend and generally play board games, sit in a hot tub, which is what you just referred to. We call it Boy Soup, which is horrible and really disgusting, but a lot of fun.

[B]

And we hate it so much, but it is memorable.

[A]

Hang out.

[B]

Just get lodged right in my brain.

[A]

Yeah, I think we've. We're about to do our fifth one in, like, a week, I think. Fourth or fifth one. So, yeah, it's a lot of fun.

[B]

That's really sweet. The Five Spurlins. Nice. You guys should have a funny name for yourself.

[A]

Like a. Like a cricket team name. Like a crew name.

[B]

Yeah. Or like a band name.

[A]

Yeah. All right. Yeah, I'll think about that.

[B]

Think about it and get back to me. While you're thinking, leave us a review, everybody. Please do it now. Five stars. Apple Podcasts. We appreciate it you ever so much.

[A]

This is where I would usually. Or you would usually describe the pattern, but we're doing an aua. We have, like, five or six different patterns entirely to talk about here. And I just wanted to emphasize the point that you made, which is these were some of the gnarliest questions we had for an aua. And I usually, in my mind, I'm like, all right, aua. It's like, light and breezy and easy, and we just show up and we just chat for a while, and then we were going through these questions. I was like, oh, my God. Like, each of these could be an episode. None of them have easy answers. This is going to be like a. A Heavier lift AUA than usual, I think.

[B]

Yeah, this is a graduate level aua.

[A]

That's right. All right, so this first one, I don't know how deep to go into this, but basically listener reached out, pointed us to a LinkedIn post and said, hey, would love your take on this LinkedIn post. I'm not going to read the entire thing. I pulled out the snippet that I think is most important. But the thing to know is basically the article was somebody giving their experience of working in a self managing team at Google. And here's the snippet that I think is worth talking about. Hire smart people and get out of their way. Only works to a point. We all know why micromanaging is bad, but under managing is also bad. Google hired smart people and gave them no direction or supervision. They occasionally did brilliant things, though often brilliant in the way a Rube Goldberg machine is brilliant, not necessarily brilliant and useful. Direction and oversight are crucial, but not because your employees are slackers and grifters who will ditch work at the first opportunity. Smart people want to do great things, but great teams and great strategies do not self organize. You have to focus your smart people in the same direction.

[B]

Yeah.

[A]

What do you think about that, Rodney?

[B]

Well, I understand it deeply. I relate to it and I understand it. And I've had experiences that feel like that. And I don't totally agree because I think that this quote supposes that the work of that kind of coherence and strategies and great teaming is predicated on a singular role creating the conditions for that. And I don't actually think that that's always necessary. So the part of this that I 100% agree with is like emergence alone is chaos. You are very unlikely to get great results with very fragmented effort and with lack of prioritization and with lack of enough investment and attention to really like make a go of something hard. Yes, fuck that up at the ready for years and years. So like heard felt, I totally get it. That being said, I don't think that like direction and oversight from a leader or a manager is the only way to get at that kind of coherence. So I think having ways of working which might have to originally be insisted upon or architected by someone who has the authority to do so, that might be where the sort of like manager or leadership role shows up. But I think once those ways of working are in place, you shouldn't have to have somebody continually monitoring to be sure that you're not doing the Rube Goldberg move. And so I think what this often looks like is like does a team or does a function or organization, whatever altitude you're playing at really have clear shared aims. Are those aims being used to prioritize resources and work? Are there accountability mechanisms baked into the team so that there's social pressure and responsibility to ship? Like, and I see this in our work all the time, both with clients and internally. A lot of these things can be created by the group. It doesn't have to be imposed by a manager or leader. So the part I don't agree with is that great teams and great strategies do not self organize. Because I think they do. They just don't do it without any structure in place.

[A]

Yeah, 100% agree on that. There's so much of this that had me nodding along from our own felt experience. And then it kind of did the thing that I see quite a bit when people are trying to take more of a critical eye to self management, which I'm all for. Like there's lots of things to be critical about with, with self management, but the one that kind of always gets stuck in my craw is the ide. Leadership and self management are these like separate ends of a continuum and you either get one or the other. And I think you did a really great job just describing how that is not the case. And that's what came up for me reading this is that, you know, I've been a part of many self managing teams where leadership is a verb that shows up in multiple different people, multiple different roles, depending on kind of like where we are in the process, as opposed to just being held by one person at one for the entire time and kind of dictating where the team is going to go. There's definitely a more mature version of self management that is not separated from leadership in general. The other thing that kind of came to mind as you were talking on this one is that the description that this person wrote up of what it was like to be on the self managing team made it seem like this team was very isolated from other parts of the organization. And if you are very isolated and nobody really depends on you to do anything specifically and nobody is kind of like expecting you to do anything, then you can just kind of go off and like follow your nose and do things that sound interesting to you. But I have seen very few functions or teams where that is actually the case. Like most teams are embedded in a network of other teams that they rely on and that they rely on. And I would just want to explore a little bit more like what is this team actually here to do and are they doing that thing? I would be more. I'd be curious about the kind of org design stuff going on around this self managing team that's just kind of doing whatever they want.

[B]

Totally. The thing I'm extracting from this that I want to just play back, that I think is a good reminder to me too is like any time you're trying to make the self organizing play work and the instinct is add a role, I'm like, before you do that, think about what ways of working are missing that you're trying to compensate for with a role. Not because necessarily adding a role or adding a manager, adding whatever is wrong. But I would much rather see a team recognize that it is doing work that doesn't matter or that it is carrying too much work in progress or that it doesn't really know what it's aiming for. I'd much rather see a team have the practices like retrospection and prioritization and adaptive strategy to come to those realizations themselves and do something about it than have one person in charge of directing and supervising others. Because the efficacy of that is just way lower than a group of people going like what the fuck are we doing here?

[A]

Yeah. And there is a certain amount of kind of psychological safety to be able to even have that conversation because I have perceived the need for that type of conversation in many organizations, but it would never happen because implicit in that conversation is we shouldn't have this job. Like our role shouldn't exist because we don't have an easy at hand answer to that question.

[B]

I mean, it's such a good point. And it's why, you know, we always talk about like how, you know, stop, start, continue, often fails because nobody will actually leave the space created by stopping anything. It's just like it's so difficult in systems that are organized based completely on growth, on growth at any cost, on consistent growth forever on no decay over time to stop and go. Like we should not do this work. It doesn't matter. Yeah, it's just, it's like almost an impossibility. And yet having had the experience of doing it, man, it feels good, man, it feels good. Like we just as, you know, like we just did a sprint at the ready with a small group of people around doing some design work around a corporate structure that we were moving toward. And like the day that it was like, are we done? Pull the meetings off the calendar. We probably have another sprint down the road, but right now, bye bye. It felt great. Yeah, it felt Great. Yeah. More of that, y'. All. All right.

[A]

All right.

[B]

Shall I ask you the next one? Yeah. Okay.

[A]

I really like the dynamic where I just get to read a thing and then you have to answer the first.

[B]

Oh, is that fun for you?

[A]

Something? It's a lot of fun. Yeah.

[B]

Yeah. Cool. You're super good at reading, so that's your job. I mean, in fairness, I'm not. In fairness, I'm not gonna give you. I'm like, oh, this is a lot of words. Okay. Okay. Could you share how you would perform project capacity planning for a people positive complexity conscious organization? I was recently hired into a division of a multinational company that is transitioning from a cost center to a profit center. So moving massive amounts of catch up work through the pipeline is top of mind. Then they talk about a bunch of traditional methods like tracking hours, et cetera, and they're still casting about to find some sort of workflow that will be sure that they're basically doing the right amount of work, not overburdening. That's it. I think that's it. I think I read the most important parts of those words.

[A]

The only thing I'll throw in there that I think a little bit of nuance in this question, which can be helpful, is this person wrote, but my leadership is still in the market for some metric or process.

[B]

Yeah.

[A]

And I think that's an interesting thing because this is not necessarily someone coming to us being like, I really need to solve this problem for me. And the problem that I have it is they're obviously getting pressure from above, from leadership, wanting to know, do people have enough work? Essentially, are we overburdening them? Are we not giving them enough? Like, how can we make sure we're getting enough all the way through? I am actually very curious in your answer because I feel like I don't have specific experience on this, but what I wrote down initially is that I am immediately skeptical of going to particularly hard metrics for something like this. And again, I don't know how long they've already been wrestling with this, but if we want to know how people are feeling about their workload, let's go talk to them. So let's just ask the folks who are working through this huge backlog of stuff like, hey, how is it going? And not worry too much about putting specific, specific numbers on it and just start gathering some stories. And, you know, I think people who are completely overburdened by what is being asked for them, like they, they wear it on their sleeve usually it's not hard to get a sense of that. So that is like the qualitative work that I would want to do first before really diving into, well, how can we like measure this in a different way? What. What do you think?

[B]

Yeah. So first of all, I really love the notion just that at least this leadership team is trying to fill but not overburden. People just like to say out loud, well done, y'. All. Because usually what we see in organizations is just how do we get more, how do we give them more and just have them absorb it without leaving or burning out or cratering? So at least the premise of the question is what's the right amount of work? Which, like, is a great premise to start from. From there though, I think that I would look for leadership first to have some design principles around workload. So they're doing this transition from cost center to profit center. What's most important? Do they want to turn a profit quickly? Do they want the backlog cleared? What's the order of operations? And the first principle is the first principle, like, we want to have incredibly high quality when we launch into the market. It's like the old adage of like, good, cheap and fast. You can only get two out of three max. I think always applies to organizations. So I would look to this leadership team to. Rather than it being like, what's too much and what's not enough, it's like, well, what are you aiming for? Is the aim that we want the backlog cleared with like purity and precision before we launch into the market? Is the aim that good enough is good enough and we need to like test an mvp? Like, let's understand what is most important because that's going to determine a lot about throughput and prioritization. From there, you know, I've come to the realization, I think you know this, Sam, but like over the last couple of years of doing so much organizational design that is very technical or design technical org design around resource allocation and strategy and prioritization and budgets and financial forecasting and very in the weeds, very nuanced, very like hard numbers. I start everything basically that I do with really deeply understanding the current state. And when I see a question like this that's like, should we be doing, you know, whatever, Agile methodology, et cetera, et cetera, I'm like, it can be so easy. Whatever team you're looking at, have them do two weeks of a calendar audit and give you the most swag of an estimation of where their time is going, how much time is hands on, keyboards, maker time, how much time is in meetings and what are those meetings about? Get to a shared picture of the current state before you develop the methodology or the outcomes that you're steering toward. Because I think that too often we go right into how should this change and what should it change to? And we miss the part where it's like, what are we designing for and what is happening now? And I usually find when we pull those two levers first, we have to change less than we think we do.

[A]

Right.

[B]

Because there's usually a lot more like rationality happening than we expect there to be. And so that's where I would start.

[A]

Totally. Yeah. That coincides with one of the things that kind of jumped out to me here is that this backlog that they're trying to get through, again, I know nothing about the work here, but anytime I see a huge backlog that has just been there for a while, I'm immediately skeptical that the only way to clear that backlog is to actually do.

[B]

Is to do it.

[A]

Yeah, totally. And a lot of times there's stuff in backlogs that if we truly are honest about what we're trying to accomplish here, we no longer actually have to do. You know, whenever I'm coaching teams, I love helping them see that the best way to finish an action or project is to realize we no longer have to do it. Like, let's maximize the amount of unneeded work that we're not doing. So I would, I would imagine we would better understand what's in that backlog and what actually needs to get done. The one last kind of tactical thought I had kind of thinking about that more people, positive complexity conscious approach to this work is that I would be trying to create a system where it's not work being pushed on to people and making sure that their plates are full and figuring out how much they need. And instead having it be a system where people are pulling things out of the backlog as they are finishing them. So everybody is filling their own plate at their pace. And you know, if you finish something faster, you're able to grab something faster. If something takes longer than we thought it would, that's okay. We're not. You're not getting a new thing pushed on you until you're finished with that. And I think that is a more complexity conscious way than some other entity trying to decide who gets what piece of work and just kind of like pushing it down to folks.

[B]

I love that. I think that's so smart. And also just to say sort of like what I was Saying before about how people cannot maintain any space in their brains or days at work. Work. It's hyperbolic, but it's a little bit true.

[A]

It's not that hyperbolic.

[B]

The same thing happens with backlog grooming, where people are just, like, reminded of an idea that their former self had and was excited about, and they cannot let go of it. And I feel like to do prioritization, well, it is necessarily painful because all of us want all of the things, no compromises.

[A]

And.

[B]

And what I lean into as someone who tends to, like, hoard my old ideas and not always be as surgical in grooming them as I should be. It's just like, if they were really good and really necessary, they'll come back up.

[A]

Yeah.

[B]

So it's like if it's sort of decayed on a backlog for six months and I haven't thought about it, and the absence of doing that work hasn't caused any problems. It is safe to kill that item for now, and when it causes a problem, it'll be back, and then we'll do something about it. A lot of times I think people think about what good work is, but they don't think about whether it is the moment for it. They don't think about the merit of the idea and the time scale together, and the timescale is just as important as how good the idea is. And that's the part that, like, very rarely gets discussed. So just like, when you're looking at the stuff and you're like, I don't want to kill my darlings, know that, like, your darlings will be back at the time when they're needed in the system.

[A]

Dang, I love that I'm about to say we. Guess we're ending the podcast here so that I can go look at my someday maybe list and kill everything that's in there. Yeah, I think I need a little bit of that in my own life as well right now.

[B]

Yeah, we need a little bit of that.

[A]

All right, question for us. So have we covered divergent slash convergent thinking yet and why traditional orgs bias toward convergence? No, I don't think we have. It's been top of mind for me, this annual planning cycle. People are vocally frustrated by the lack of alignment on a 2025 strategy. And it's October. This came in a couple of weeks ago.

[B]

Clarifying question. What do you make of the 2025 strategy? And it's October. Like, is it that we're close to it, or is it that we're still months Away from it. I didn't understand.

[A]

Months away. And I think we have time to, like, figure that out. Like, we still have like three months here. That's my interpretation. And the listener, I'm sure, will email us if we get that wrong. But my understanding of the scenario, that's kind of what's. What's going on here. Everybody is so, like, we gotta converge on the thing that we're doing in 2025. And, you know, it's the middle of October. Like, what's the hurry to converge on the strategy?

[B]

Yeah, okay. It's funny how depending on where you sit, I feel like that could be read in different ways.

[A]

Different ways. I know.

[B]

I was thinking clients of mine who would be like, it's already up October. How are we still arguing about this? And we're like, oh, my God, it's months away. Who knows what could happen? Okay. My first hot take of the podcast. I hate the word alignment.

[A]

Please.

[B]

What does it mean? What does it mean? I feel like it's one of those words that people use and they don't know what it means. And everybody nods and goes like, yup, yeah, and no. Does it mean we agree? Does it mean we're doing it? Because we are going to fall in line whether we agree or not? Does it mean that we are going to do something that is supportive and related in a line with. I don't understand what it means. And I hear it constantly, especially around strategy, and I find it very confusing. And I wish people would use a word that actually means something like we agree or we consent or we disagree or something that I can understand.

[A]

Yeah. And I love that. I think generally what alignment tends to mean is we're done arguing that.

[B]

It means we give up.

[A]

Yeah. It's like, we're not continue to talk about this and now we have alignment.

[B]

That is so true, Sam. And I've definitely been in meetings of leadership teams where it's like, what we're going to do today is get to alignment. And what that means is at the end of this meeting, we're going to stop talking about this.

[A]

Yeah.

[B]

Yeah. But there's no definition.

[A]

It's just going to go under. It's going to go underwater at that point.

[B]

Yeah, exactly. And when later we diverge and people are doing shit that makes no sense according to our aligned strategy, we're going to have to get realigned. How many times have you seen realignment drills in organizations?

[A]

Quite a few.

[B]

So many times. And I. Maybe part of it is because nobody knows what the Fuck that word means. So then they're just like, we're aligned, Salute. And then three months later, we, we ain't. Secondly, I think that organizations are bad at having real conflict because conflict brings up their midnight zone stuff. People have very different relationships to conflict and disagreement and what it means for them in terms of their stability and their safet and their feeling of belonging and their feeling of connection, et cetera, et cetera. And so I think at the root of convergence is we don't want to be in conflict with each other. And so I think in a lot of strategy conversations there is this real seeking and adamancy around convergence that is mostly unnecessary. And I'm like, what do we even get for that? Like, first of all, if we think of the 2025 strategy as an experimen to be steered quarter on quarter, who fucking cares? Second of all, if any strategy is actually at a strategic level, you're going to have to do a bunch of work to clarify decision rights and workflows and what's happening at the team level and resource allocation to bring it to life. And that's where like the real rubber meets the road, for lack of a better term. So the whole notion of convergence feels sort of like the notion of alignment to me, which is that it is something that makes us feel like that we're connected and that we're coherent and that we're not having friction with the people around us who we're meant to be cooperating with. But actually it doesn't mean anything.

[A]

Yeah, I agree with all of that. And I think what I would add to that list of things that we are seeking by trying to get to convergence is just certainty. I think a lot of the dysfunction within organizations can be understood best through the lens of what will make us feel the most certain, the most quickly. And I think getting to convergence on the 2025 strategy allows us to all pretend that we are certain about what is going to happen in the future and how we are going to respond to it. And we can focus on just executing. Yeah, on that. And I think that is the cornerstone of a lot of these sorts of exercises where we would actually benefit from kind of sitting in the mess a little bit longer and being more divergent and getting more creative about what we could do. But because we're trying to, all of us kind of together, step away from the cliff of uncertainty, we just quickly converge on. Okay, yep, this sounds good. Now we aren't fighting. Now we have alignment. Now we know, and we can kind of go Put our heads down and do that work.

[B]

Totally. I also think that, you know, the best strategies that I have seen and that I have outsized impact do tend to be counterintuitive. So strategy, this incremental strategy that just feels like the penny drop as soon as you read it. Those don't tend to be the strategies that light the world on fire. The ones that tend to be really provocative and really like, is that gonna work? Tend to be the things that are real game changers. And I say that because it requires listening to real edgy thinking and really like actually divergent perspectives. Not like 10 degrees off, like 90 degrees off to get at that. And I was once facilitating an executive team of a high growth tech company and I remember very clearly it was the first time that the VP of engineering was invited in addition to the CTO and they were working on essential intent stuff. And the VP of engineering was basically like, we are investing in and have been investing in the wrong product, full stop. This other thing, this side project that's gotten sort of 10% of the attention is the future of this company for the following reasons and to these guys credit, they like really stopped and were like, oh, and we didn't do anything else that day except interrogate this idea that this very quiet signal was actually the future of the organization and therefore should be prioritized as the prevailing strategy. They went to dinner, got wasted, and the next morning when I saw them, that's where they were. And that guy was right. And it's like if they had been striving for convergence, they very nearly had it. And it looked a lot like the prior seven years, but they really allowed, to your point, this period of time to just be like, maybe we've got it wrong or maybe there's a better option out there. Let's spend the time to think about it before we rubber stamp it and move on.

[A]

Yeah, no, that's really interesting. One last thought. I'm aware of extra context in this question, which is this is a market leading organization within a larger tech firm. And what I'm thinking about here is how I think sometimes functional strategies push to premature convergence because ultimately they need to feed into like somewhere else. Like there are other functions doing similar exercises and like, well, we need to wait until the marketing strategy is done or we need to wait for the product strategy to be done before we as the marketers can do it. And, and I think most organizations would be better off having more strategy conversations that are truly cross functional and breaking out of functions. You know, you can't do a marketing strategy that is purely full of marketers. Just have some token invitation of other functions. Like I. You get into a unhelpful, unhealthy pattern. If that is how strategy is developed and kind of rolled out in a very large organization.

[B]

A hundred percent, I dig it. Yeah. You know, there's a tagline at the ready that is like your strategy is cross functional. Your organization is not. I just believe that that's true. Like I just, I don't see a place where strategy will stay contained to a silo. At least not an interesting strategy.

[A]

True, true. Just garbage strategies.

[B]

Yeah, just poop strategy. Okay, next question. I continually see a pattern where identifying and starting a project is easy, but then when competing priorities arise, the work is dropped in favor of billable work. No shit. This is especially true in teams where people's day jobs are a primary source of revenue for the business. Sounds like. Yes. And the initiatives are internally focused. Also sounds like us. This feels like a two sided problem leadership sending conflicting messages about what the bigger priority is and then teams not flagging when and why work gets deprioritized. The result is a lot of zombie initiatives and dissatisfied people on all sides. I'd love some different ways to think about this.

[A]

I'll say 80% of this question sounds like it was written from somebody at the ready.

[B]

Like, did you submit this?

[A]

I. I did. I did not.

[B]

What a super weird burn. Sam starts submitting questions that are just like, yeah, what the fuck are we doing?

[A]

That's a good idea. Someone.

[B]

That's a great idea.

[A]

Okay, I haven't thought of that yet. Yeah, I mean this is the thing. Especially if your day job is, you know, doing consulting work and especially if.

[B]

Your day job is the service business that makes the monies.

[A]

Yeah, exactly. So I think you probably have a lot of really interesting things to say about this. As like always your role at Source. As always. You're right.

[B]

Thanks.

[A]

We've done a lot around this, I think to get better at it. I mean the really glib answer is that anything that is felt and resourced and incentivized and reputationally incentivized as side of desk work will always be dropped in favor of the stuff that keeps the lights on. And if you want that to not be the reality, you need to start taking steps towards a reality where that work and the revenue generating work is all just work and it's all treated the same and only then does it have a shot at kind of getting the respect and the spotlight that it needs to actually get done.

[B]

Totally. One of the things that we've done that we're about to do more of is separating explore teams from mission based teams. And I'm going to ask you about this because I would consider you to have been part of two different explore teams teams. An explore team at the ready is a very small, like truly max, two people group who in a very short period of time, like less than eight weeks, with a very small amount of money, like less than 15 grand, can go validate whether there is a real problem to be solved. And a lot of times we skip this step in services businesses because we go right to what can we make and sell or we can do anything. So we might as well do this thing. And I think it's very easy for companies to spin up an internal initiative or a tiger team, or a side of desk project, or even a well crafted mission based team without first doing the exploration of is there a real problem here worth solving? And I think you came to different conclusions in two explorers that you've been part of. I'm thinking of dao and partnership. And I'm just curious, like for people who listen to that and go, that seems interesting, I have no idea what that would look like here. How did that actually work for you?

[A]

Yeah, so I mean both were very clean in the sense that the organization essentially said, hey, ignore your responsibilities to generate revenue for now and do client work and instead go off and explore this thing and come back and kind of tell us if we should invest more. So first was the dao stuff that Tanisi and I did together. We could do so much about like what was going on with daos and crypto in 2021. A lot of noise that, you know, I think in hindsight it feels like we should have came to a conclusion sooner on. On that than we ultimately did. But there was so much froth and so much interesting work kind of happening there that we did kind of hang out there for a while. But ultimately it's not like we have a growing crypto dao business right now, like we decided at this moment time or there's no reason for us to invest further in that. The other interesting thing in retrospect there is that definitely learned that our services and expertise are incredibly valuable to daos. Like we were helping daos quite a bit actually with what we are good at and what we were doing with them. But that is different than there being a problem in the market, I. E. Pay us money that we need to sustain our business. Model to actually do this work. So yes, there's a problem to solve. They will happily accept our help, but no, not actually pay us in real money. That actually is useful.

[B]

Before you go on to partnerships, let me just respond to the DAO one because here's where I see companies get it wrong. They do something like that. First of all, they don't really, they don't really put aside the money and the protected space for a good revenue generating team to go learn something, but they should because they're never going to learn it otherwise. And two is there are a lot of companies who would hear what you just said and say that was a failed experiment or that was a failed exploration.

[A]

Right. Incredibly successful exploration because we got very useful information.

[B]

It was an incredibly successful exploration for two reasons. One is the point that I just made in the last question about idea versus timescale. We had the timescale wrong, but the idea is right. Like there will eventually be something like daos that are a different way of organizing that will meet us in space and time in such a way that they can make use of and digest our work and they can pay us for it. Like that will happen. So it was worth understanding that landscape. And to me, more importantly and more presently, we made relationships through that project that like are incredibly valuable in other ways. Like I still talk to someone regularly that we met through the DAO exploration about what pro social rewards are and how to think differently about full comp stacks at the ready and what ownership should mean in a non traditional capitalist system. Like I never would have met that person if we had not gone down the web three rabbit hole. And so I say this because it's like those three or four relationships that like we've maintained with people through that well worth the price and time invested because those are like perpetual thinkers outside of our space doing very modern organizational design that I feel very grateful to have access to.

[A]

Yeah, totally. And I see you jotted down here. Emotional response. I don't know if this is what you're referring to, but for me I at the end of that felt like a failure initially because I saw how much money we invested in it. And it's easy to tell this story of like, I am, you know, Tanisi and I, we're going to go off and create this new like incredibly revenue generating arm of the READY and you know, go us and like that's not how it ultimately shook out. It kind of like fizzled and then we officially like stopped it now separated from it. I completely agree. It was successful experiment. I learned a lot about Web3 and DAO stuff that I'm always going to have like in my brain ready to go when it'll be useful again. But the, the short term emotional response was like, wow, I blew that one. But I don't think I would. That was also like the first, first kind of explore team that I had led at the ready. And I don't think I would have that same emotional response again just to.

[B]

Stay on the emotional response. And I think it's very related to this person's question. That's a very valid response. And we were very thoughtful as a company when we funded that initiative that that was money we could lose.

[A]

Yeah.

[B]

So even if we hadn't gotten shit from it, which we did, but even if we had, they're not even all going to produce the kind of intangibles that I'm describing right now. Even if we hadn't gotten anything, it doesn't matter because you have to invest some real money in innovation and inherently, if you're doing it right, they're not all going to be winners. Because if they're all going to be winners, it's not innovation. So like, yes, I get the emotional response. It's very valid. And the people that we hire at the ready are people who want to like, like contribute and be successful at everything they do. And like everyone came from a gifted and talented program and that's our own cross to bear. But the flip side of that is like, if you do this correctly from an org design perspective, it. Some of them are meant to fail and bound to fail and that's why you don't invest an amount of money that is not safe to lose.

[A]

Yeah, for sure. If you are kind of hinging on this innovative idea or project to hit to save the company, like, like you've already kind of lost the plot at that point.

[B]

You've already lost the plot. Yeah.

[A]

Yeah.

[B]

How was it similar or different the second time you did it?

[A]

So the second time you're a little explorer, little explorer guy. It was a shorter period of time. It was only a couple of months and it was mostly solo. I didn't have like Tenisi with me. It was actually really helpful to just have another person in the weeds kind of as we were learning new things together. It's different with partnership. Like we weren't learning a lot, like new technology or anything there. I found it interesting and really challenging. Again, I don't know that we didn't come out of it with like a huge New partnership that like changed the face of the organization. I think we came out of it learning that partnership for partnership sake. Absolutely not worth it. So much work and effort to make partnerships a useful thing. I don't think we like have closed the door on other interesting partnerships in the future, but at the end of that explorer, it wasn't like we had a long list of high probability partnerships to go make happen.

[B]

Right. I mean, here's the thing. Sometimes, and this is for the original question asker that like, you know, your leadership is sending conflicting messages, et cetera. So consider me to be the voice of leadership in this particular scenario. For better or worse, use that as a proxy. We had had such random and not thoughtful swings at partnerships for years at the ready, including things that I personally carried where it was like, you seem like us, we should be doing something together with sort of the vibe of like, is this a big enough tent that a bunch of like minded people doing sort of similar work should be under it together. And basically before you did that explore, I couldn't feel certainty of whether it was possible or not. Not. We needed someone to have real opportunities with real potential partners and real clarity on like what the value prop was going to be and what was complementary, etc. In order to disprove the hypothesis of the Big Ten.

[A]

Yeah.

[B]

And disproving that has probably saved me a hundred hours in the last two years of talking to people who are like, we should collab. And I'm like, we're good, good.

[A]

That's such a good point that I think before we did that explore, I at least had this vague sense, like we have a bunch of really easy, really lucrative partnerships that we just haven't like buckled down to go find and like make happen.

[B]

Exactly.

[A]

And then I spent like three months trying to do it. I was like, oh, that's not how this works at all. Yes, I feel a lot better now.

[B]

Yes. But sometimes you have to make the investment in order to know with certainty that you should turn off the faucet.

[A]

Yeah.

[B]

And like that to me is just as valuable as if a banging partnership had come out of that explore.

[A]

Did we solve this for this person?

[B]

Well, no. Yes, no, no, and yes. So here are the only additional bits that I would throw in to the stew. One is do an explore before you launch a mission based team to validate that there is a real problem. The mission based team is where you start to come up with the solution for the problem. Everybody wants to rush to the solution making, so don't skip that Explore step. And then when you are like, this is a problem that is worth solving, that is significant for us. And based on this person's question, like, that could be like, yeah, no shit, we really need a hiring process. Or, like, no shit, we really need to rethink our compensation. Or like, no shit, our sales strategy is garbage. Like, a real validated problem that's worth solving. Now we launch an mbt. And, like, we've talked about those a lot on this show. Go listen to an old episode, but make sure that before you organize roles around the work that you know what the solution is that you're creating and you know that somebody would actually buy it from you. And then the only other thing.

[A]

Including internal.

[B]

Including internal.

[A]

For something for ourselves internally.

[B]

Exactly. Because we see internal functions make shit all the time that nobody wants. Real product mindset stuff is important. The last thing is what I actually meant by emotional response that I just really felt it come through in this question is, like, we're just generally much more equipped and able to disappoint each other than we are able to disappoint our clients. Like, we're just 10 times out of 10 going to say to each other at the ready, I didn't get to that because it was a wild week at the client. Then say to the client, I didn't get to that because of this internal initiative at the ready. It's just not going to happen. So just, like, know that that is how it is and plan accordingly rather than expecting that it's not going to be like that. You're always going to tell your home team to fuck off before you're going to tell your client.

[A]

Yeah. Which is why, if you really want to do this, change somebody's home team to the internal thing, relieve them from that kind of dual commitment to external and internal.

[B]

Exactly. Sam. Should we wrap it up?

[A]

Let's wrap this up. As you know, we're always looking for new topics for the show and apparently pull apart metaphors. So if you have an organizational pattern that you're having trouble changing, shoot us a Message [e-mail] this show is engineered.

[B]

By Taylor Marvin and produced by Jack Van Amberg, who, based on Today, has literally limitless patience with Sam and I and our inability to plug things in at work with the Ready is created by the ready, where we help organizations around the world change the way they work. Thank you so much for listening.