AUA: Why Is My Small Org So Hard To Run?

Summary

Episode Overview

Title: AUA: Why Is My Small Org So Hard To Run?
Hosts: Rodney Evans & Sam Spurlin
Date: March 16, 2026

This special "Ask Us Anything" (AUA) mini-episode addresses a listener's question: Why do small organizations feel so difficult to run, especially concerning intangible deliverables and multiple stakeholders? Rodney and Sam break down how workplace challenges and modern organizational practices apply to small organizations, highlighting unique complexities, missed opportunities, and the pivotal role of interpersonal dynamics and structure in shaping small teams.

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Key Discussion Points & Insights

1. Small vs. Large Organization Complexity

• Big ≠ Complex:

  • Sam clarifies that complexity isn’t exclusive to large organizations. “Smaller organizations are also complex in the complex adaptive system sense of hard to predict and control…” (01:14)
  • In small orgs, individual personalities and relationships have far greater impact on operations and outcomes.

• The Human Element:

  • In small orgs, “it’s much more human in some ways. ...When you’re a team of like 10 people, it’s like, ‘Mary sucks and Jim can’t get his shit together.’” (01:44, Sam)
  • Large orgs may depersonalize conflict (“this process and like this team in these roles”), but in small orgs, issues are felt directly and personally.

2. Missing vs. Excessive Structure

• Small Orgs:

  • Rodney points out that smaller orgs often lack explicit operating models, steering mechanisms, or principles-based budgeting. "They don't have a way..." (02:30)
  • The work with small orgs is about installing “minimum viable structure to tame the chaos and unlock capacity” (03:14, Rodney).

• Large Orgs:

  • Large orgs, by contrast, suffer from too much structure. The challenge becomes unwinding processes and removing unnecessary bureaucracy.

• Same Ideas, Different Application:

  • “The ideas are largely the same, but the motion is different...” (03:10, Rodney)

3. The Threshold of Awareness and Change

• Size Transitions:
  • There is a qualitative transition as organizations grow:
    • “Prior to this moment, everybody was involved in everything...” (03:46, Sam)
    • Eventually, it’s not possible for everyone to be aware of everything – a significant point for both logistical and emotional adaptation.
• Not a Precise Number:
  • No exact “Dunbar’s number,” but probably under 50 people (04:39, Sam & Rodney).

4. Practical Takeaways

• In small orgs:
  • Don’t conflate “small” with “simple.”
  • Be deliberate about putting in just enough structure to clarify operations and unlock productivity.
• As orgs scale:
  • Anticipate the emotional impact as decisions and conversations begin to leave some people out.
  • Iterate and experiment: There’s no perfect blueprint—adapt as you grow.

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Notable Quotes & Memorable Moments

• On small org complexity:
  “Smaller organizations are also complex in the complex adaptive system sense of hard to predict and control and need to iterate and experiment to understand what is happening. That is true even in small organizations.”
  — Sam, (01:14)

• On the human dynamics of small orgs:
  “When you’re a team of like 10 people, it’s like, ‘Mary sucks and Jim can’t get his shit together.’ And so it’s much more human in some ways.”
  — Sam, (01:44)

• On installing structure:
  “In the smaller space it tends to be more chaotic because there’s missing constraint. And in the big organizations it tends to be overly bureaucratic because there’s too much constraint.”
  — Rodney, (02:52)

• On the qualitative tipping point:
  “There’s this like qualitative moment that you hit where prior to this moment, everybody was involved in everything... And then there is a point that you hit where that can no longer be true...”
  — Sam, (03:46)

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Timestamps for Important Segments

• 00:52 – Listener’s question introduction
• 01:11 – Complexity in small organizations
• 01:44 – Personality impact and interpersonal tensions
• 02:26 – Small orgs and missing structure
• 02:52 – Chaos vs. bureaucracy: missing vs. excess constraint
• 03:46 – The transition point in org growth
• 04:39 – Approximating the org size that defines this shift

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Overall Tone & Language

Rodney and Sam maintain a candid, conversational style, using direct language and relatable workplace anecdotes. Their tone is pragmatic, empathetic, and peppered with humor (“Mary sucks and Jim can’t get his shit together”) while offering actionable insights for leaders of small organizations.

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Summary

This episode powerfully debunks the myth that only large organizations wrestle with complexity, revealing the unique—and often more personal—challenges of leading small teams. The core advice: install just enough structure to reduce chaos, expect emotional bumps as you grow, and remember that adaption trumps perfection. Whether you’re in a four-person startup or a scaling nonprofit, The Ready’s insights give you practical moves to improve your small team's ways of working.

Transcript

[A]

Hey y'. All. We are getting ready to record an ask us anything episode and we're sending out the bat signal because we want to hear from you.

[B]

That's right. If you've got a thorny workplace problem you need help with, shoot us a message on LinkedIn or email the [e-mail]

[A]

these episodes are my favorite episodes to make and we cannot wait to hear what you send us. So please do it. Thanks so much and as always, please enjoy the show.

[B]

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

[A]

Hey Sam.

[B]

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?

[A]

Alrighty. This week's question is, you seem to be often talking about big organizations with complex systems. How do you think about the application of ideas to smaller organizations, especially when there are intangible deliverables or multiple stakeholders?

[B]

So I think everything we talk about is relevant to smaller organizations too, just in slightly different ways. And I think one thing that I just want to call out in the question just to make sure that we're not equating big and complex as the same thing. Smaller organizations are also complex in the complex adaptive system sense of hard to predict and control and need to iterate and experiment to understand what is happening. That is true even in small organizations. And sometimes in some ways they're even more complex because I think in a small organization, individual personality and individual interpersonal stuff has a larger impact on how things go in the organization. I think pretty quickly in larger organizations you get to like, you can have pretty emotionless, kind of like faceless conversations about what's going on. It's like this process and like this team in these roles. And then when you're a team of like 10 people, it's like Mary sucks and Jim can't get his shit together. And so it's like, it's like much more human in some ways. So yeah, I think, I think it applies. But often there's like simpler versions of the stuff that we're, that we're talking about.

[A]

Yeah, I think that most of my experience working with small to mid sized companies is that they are missing the application of our ideas. Like those ideas have not been installed. So they don't have a way of conceiving of their operating model. They don't have a way of steering their strategy. They don't have A way of doing principles based budgeting like they don't have a way. Whereas at the other end of the spectrum, larger institutions, more of the work tends to be trying to refactor or take away existing structure. So in the smaller space it tends to be more chaotic because there's missing constraint. And in the big organizations it tends to be overly bureaucratic because there's too much constraint. The ideas are largely the same, but the motion is different because on the small end, you're in stock installing minimum viable structure to tame the chaos and unlock capacity. And ideally you're pointing that at the leverage points that are going to get you the absolute most. On the bureaucratic end, mostly what we're trying to do is get people to stop doing wasteful shit.

[B]

Yeah. I think there's a transition point in small organizations which I don't know what the number is necessarily, but there's this like qualitative moment that you hit where prior to this moment, everybody was involved in everything.

[A]

Yeah.

[B]

And like any sort of experiment, we all do, we are all aware of things. We're all kind of like in the same channels and we all kind of have the same situational awareness. And then there is a point that you hit where that can no longer be true and it's not a clean binary. And you can like kind of get it wrong at first. In that initial transition of like the first time, people are not part of what feels like the main conversation and like the feelings and stuff that come up with that. I think it's a really interesting point. And if we're talking about organizations that haven't quite hit that, I think this work kind of really starts to change a little bit when it's not everybody is completely aware of all the things all the time. And I don't know if that's like a specific number. I don't think it's. It's not like Dunbar's number, I don't think, but maybe. I don't know, it's. It's probably less than 50 people.

[A]

Yeah. Yeah, I think that's right.

[B]

All right, that's it for this mini. If you've got a question of your own, hit us up at [e-mail].

[A]

we will see you back here next week for a full episode of At Work with the Ready. Thank you so much for listening.