AUA: How To Design a Startup OS From Scratch?

Summary

Episode Overview

Podcast: At Work with The Ready
Episode: AUA: How To Design a Startup OS From Scratch?
Hosts: Rodney Evans and Sam Spurlin
Date: January 19, 2026

Theme:
This listener-submitted AUA (Ask Us Anything) episode tackles the foundational question: "How would you design an organizational operating system (OS) from scratch for a brand new company?" Drawing from their extensive experience in helping organizations rethink how they work, Rodney and Sam offer practical advice for intentionally building systems, rhythms, and structures—without overengineering from the outset.

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Key Discussion Points & Insights

1. Start Small: Resist Over-Designing Your Org OS

• Both hosts emphasize not to overcomplicate things at the beginning.
• Sam's Principle: "Resist the urge and keep the phrase minimum viable everything in your head." (00:36)
• The team should avoid creating elaborate systems for hypothetical problems; build structures as real tensions or challenges surface.
• Rodney’s Advice: "Wait until it hurts—don't try to do stuff until there is a shared, recognized pain caused by its absence." (01:45)
• Overproduction of frameworks or scaffolding is a common smart-person trap, often creating unnecessary work and confusion.

2. Defaults: One Size Does Not Fit All

• There's a danger in developing universal systems for everyone, as needs differ by team or role.
• Rodney shares a story of a client who built an impressive but overly general strategy framework, which ultimately didn't fit everyone’s needs.
• Rodney: "There is no one size fits all in Org design. There are defaults that you can start from, but they are inevitably going to be adapted based on what the work is to be done." (03:18)

3. Establish A Lightweight Operating Rhythm

• Early focus should be on creating a simple, sustainable cadence for reflection and adaptation.
• Sam: "...get your default operating rhythm up and running immediately. Some sort of cadence: regular strategy conversations, a regular cadence on retros..." (03:54)
• Even solo founders can benefit from self-reflection meetings (e.g., weekly action planning).

4. Non-Negotiables: Kanban, Operating Rhythm, and Experimentation

• Rodney: "The three things that I don't understand how companies live without are some kind of Kanban board... a backlog... and you got to have an operating rhythm." (04:39)
  • Kanban Board: Visualize workflow—absolute must-have for context switching and prioritization at any stage.
  • Backlog: To prevent losing track of tasks and priorities.
  • Experimentation Template: A simple proposal method and a means for team consent help institutionalize safe-to-try experiments.
• Rodney: “Just make one. Also, I can't live without a backlog, you guys. ... Got to have an opera them.” (05:06)

5. Strategy: Sky-Sensing Before Grand Plans

• The hosts distinguish between high-detail planning (usually unnecessary at the start) and “sky-sensing”—the practice of regularly stepping back to observe external trends and environmental context.
• Sam: "It's really important to build the muscle early that we're looking at the sky and that we're talking about it." (07:22)
• Detailed planning is less valuable than cultivating the habit of collectively noticing and discussing the outside world and its possible impacts.
• Rodney: "People want to start with the plan, but actually getting really good at talking about the environment makes the planning a lot, a lot easier." (08:20)

6. Strategy vs. Planning—They're Not the Same

• The hosts caution against conflating "strategy" with detailed operational planning.
• Sam: "Planning and strategy work are two different things and different conversations." (09:11)
• Many teams confuse the two, which undermines both efforts.

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Notable Quotes & Memorable Moments

• Sam Spurlin [00:36]:
  "Resist the urge and keep the phrase minimum viable everything in your head."

• Rodney Evans [01:45]:
  "Wait until it hurts—don't try to do stuff until there is a shared recognized pain caused by its absence."

• Rodney Evans [03:18]:
  "There is no one size fits all in org design. There are defaults that you can start from, but they are inevitably going to be adapted based on what the work is to be done."

• Rodney Evans [04:39]:
  "The three things that I don't understand how companies live without are some kind of Kanban board... a backlog... and you got to have an operating rhythm."

• Sam Spurlin [07:22]:
  "It's really important to build the muscle early that we're looking at the sky and that we're talking about it."

• Rodney Evans [08:20]:
  "People want to start with the plan, but actually getting really good at talking about the environment makes the planning a lot, a lot easier."

• Sam Spurlin [09:11]:
  "Planning and strategy work are two different things in different conversations."

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Important Segment Timestamps

• 00:20 – Listener question introduction: How to design an org OS from scratch?
• 00:33-01:45 – Sam and Rodney on resisting overdesigning and embracing "minimum viable everything"
• 03:18 – The dangers of universal frameworks and need for adaptation
• 03:49-05:44 – The essential first steps: establishing operating rhythm, Kanban, backlog, and experiment methodology
• 07:04-09:11 – The value of sky-sensing (sensing the environment) and the distinction between strategy and planning
• 09:37 – Rodney on facilitating sky sessions and why they're crucial (with a plug for The Ready's offerings)

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Conclusion

Rodney and Sam distill decades of experience into a clear philosophy:

• Don’t overbuild—start with the minimum viable systems.
• Let real, shared pain points drive process and system development.
• Set early habits around rhythm, visual workflow, and scanning the environment.
• Continuously adapt, rather than seeking one-size-fits-all solutions.
  By focusing on these principles, founders can lay solid groundwork without accidentally creating bureaucracy or complexity before their company truly needs it.

Transcript

[A]

Hey, everyone. Welcome back to OrkwithReady. I'm Sam Sperlin and I'm joined, as always, by Rodney Evans.

[B]

Hi, Sam.

[A]

Every other week we're tackling one tough, thought provoking listener question and sharing a few ideas that might help. Let's dive in. Rodney, what have you got for us this week?

[B]

Oh, this is good. This is a banger. All right. How would one start an org os if you start from scratch as a completely new company, someone starts with no baggage. How would you do it?

[A]

I would resist the urge to get super fancy about it, totally. You are probably. I don't want to make assumptions about this person who asked the question, but they're listening to our podcast, so you're probably a nerd, A bit of a nerd. And I think the overwhelming urge when presented with a blank canvas and a lot of knowledge about what could go on that canvas is to do a bunch of stuff early on, defining things and creating systems and all of that. And I would say resist the urge and keep the phrase minimum viable everything in your head. As you get started here, really latch onto the idea of using tension to drive decisions and structures and things that you need as you experience it, as opposed to predicting, predicting what you think the tensions are going to be and preemptively creating stuff. And obviously you can go too far in either direction here. There are some things where if you make decisions early on, you prevent lots of pain later. But I think those things are fewer and far between than you might think.

[B]

Yeah, plus one. You know, I had a, I had a card in here that just said, wait until it hurts. Like, don't try to do stuff until there is a shared recognized pain caused by its absence. Just don't learn from our combined, I don't know, 35 years of experience, wait until there's pain to even try the other thing. And I think we should talk about defaults after this because you and I have slightly different views on what they should be. But something that I've noticed in a couple of projects recently is there's a real tendency for smart people to create too much scaffolding or envision scaffolding and then try to apply it consistently at every altitude. Yeah, and here's what I mean by that. I was just working with somebody last week. She's really fucking smart. Like, really makes me feel like a dumb, dumb sometimes. And she, she had created this, like, strategy framework that was really good. Like it was an MBA level framework. I don't have my mba, so I had to Read it a few times. But the thing that was tricky about it, and this is what happens a lot with OS moves, is here's this beautiful thing that is kind of perfect. Now we're gonna do it to everybody. And it's like, what's not. I don't know what the scale of your company is, but like what's necessary for the team that's stewarding and what's necessary for the individual contributors in terms of direction and scaffolding to prioritize is very different. And the same is true of operm and the same is true of strategy work and the same is true of experimentation. There is no one size fits all in Org design. There are defaults that you can start from, but they are inevitably going to be adapted based on what the work is to be done. And so my follow up to Wait until it hurts is don't try to create something that will work for everybody.

[A]

Yeah. To give a little bit more specific of an answer than my first one, I do think what is worth figuring out or establishing very early on are the, the operating rhythm that allows you to channel tension into new things. So I would get your, your default operating rhythm up and running immediately. You know, some, some sort of cadence, regular cadence strategy conversations, a regular cadence on retros. To the extent that there's a group of people working on shared work together, which maybe if you're a very small new company, maybe it's just yourself, you know, doing like an action meeting for yourself every week where you're getting really clear on the work to get done. That rhythm in that basic form will serve you really well as you start to bump up against the pain of a growing organization.

[B]

Yeah, I think that's right. I mean, you know, I'm obviously like operating Ride or Die. The three things that I don't understand how companies live without are some kind of Kanban board. Dude. When I'm in a company, when I'm working in a team, like especially like a leadership team and they don't have like a Kanban board to visualize their work, I'm like, how do you live your life? Like, I feel like I'm on a lot of teams between client teams and ready teams. And like the Kanban board is home. It's where I go to be like, what do we do now in this meeting? Like, what do we talk about here? And if we didn't have those things, not just for my own work, because frankly at this point in my career I have fewer projects on all of those boards than Everybody else, but, like, just to not lose the plot on context switching. I don't understand how people function without a Kanban board. Just like, make one. Just make one. Also, I can't live without a backlog, you guys. I could. We could talk about this forever, but got to have an opera them.

[A]

Dangerous. Getting dangerously close to like a therapy session for you right now, Rodney.

[B]

I know. I just. I can't stand it. I just can't stand. Makes me unwell. It makes me feel unwell. So you got to have a board. You got to have an opera them. And I think the lightest possible method for experimentation and probably the lightest possible method is some kind of proposal template. We talked about that in like, a very recent episode and I think we linked to one, a very light proposal template. Some way of the team consenting to those proposals. And like one column in that Kanban board where you're tracking live experiments so that you're not letting them become zombies. I think if you do three things, it should be those three things for like six months. Because I would tell you I have rushed to do strategy clarification with teams and found at the beginning they're so overwhelmed with the amount of work that they have going on that they can't do the strategy thing yet. Like, they don't have enough clarity and coherence as a group to name things. And we just have to sort of like get the house in order before we decide, like, what town we might want to move to and start looking at new houses.

[A]

Yeah, I know I have strategy here as one of my points that I was going to make. And I actually agree with you because I think what I am referencing when I. When I say that strategy is worth kind of being a place where you do some initial work if you're using kind of the OS canvas as a lens, is that I think it's really important to build the muscle early that we're looking at the sky and that we're talking about it. So I think the incredibly detailed strategy work that a lot of organizations do by default or people have experience by default, especially early in an organization, not worth it. It's just. It's just fiction. But the practice of, like looking up at the sky and understanding what's going on and making sense of it and maybe making some hypotheses about how things are going to be affected, that I think should start as early as possible. And your organization.

[B]

I totally agree. And even if it's, you know, we've talked about sky sensing before on this show, I was just in a Sky session yesterday at the Ready with the State of the Biz crew. And the thing that's so important about doing that work, about really looking at externalities and trying to sense the future, is, like, if you don't do it, you'll never get good at it. And, like, Mia is, like, really smart about how she designs and facilitates those sessions for us, our chief of staff. And one of the principles of those sessions is, like, us learning to become futurists. Like, of course, it's about sensing the market and understanding and adapting our strategy as a result of real data and trends. We're noticing and having a diversity of perspectives. But also the call to doing that work is get good at noticing what the fuck is going on and what's coming. And yesterday she had us, like, look back at sort of last month's trends and be like, how close were we? Where did we really miss? What did we really not see? I'm saying this just to double down on your point, Sam, that, like, people want to start with the plan, but actually getting really good at talking about the environment makes the planning a lot, a lot easier.

[A]

Well, and the fact, too, that planning and strategy work are two different things in different conversations, which also, that, though.

[B]

That I would say is not broadly understood.

[A]

No, no, of course not. Yeah, I'm right there with you. And if you have been listening to the last three minutes and you're like, sky, what the hell are they talking about? You should go back and listen to the depth finding miniseries where we talk about depth finding and sky being the layer at the very top where all of the external stuff lives.

[B]

Also, if you are someone who needs help with this, you should just hire us to do just a Sky session. Like, it's such a good. Everybody wants us to come and do a strategy session for them. And I get why. It's because they want an asset at the end that feels like now we're in control of our destiny. But actually, like, the sky thing is not that easy to do, especially if it's an atrophied muscle in your leadership team. Yeah. So, like, call us and let's do that.

[A]

All right, that is it for this mini. If you've got a question of your own, hit us [e-mail] we will see.

[B]

You back next week for a full episode of At Work with the Ready. Thank you for being a listener.