At Work with The Ready

Most leaders want to believe they're building something durable: a company that matters, a culture that sticks, a system people can rely on. But what if most organizations don't have the staying power of a great city like Venice...and instead are more like a gold rush town? What if that same company is more likely to change you than you are to change it?

In this episode, Sam sits down with John Cutler, writer of The Beautiful Mess and Head of Product at Dotwork, to pull on the threads John has been obsessively following for years: how organizations actually work, why seeing patterns and being able to act on them are completely different skills, how leadership is like game design, and why embracing the mess might be smarter than chasing clarity.

Learn more about John and Dotwork:

Read his newsletter

On LinkedIn

Dotwork

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Mentioned references:

Dr. Cat Hicks

John's post about "the slide"

W. Edwards Deming

"Hollow Knight and Silksong"

John's post with Tom Kerwin

Ashby's Law of Requisite Variety


This Beautiful Mess (the emo band)

John's old Medium posts

North Star Framework


Team Topologies, book by Matthew Skelton and Manuel Pais

00:00 Intro + Check-In: What was your first job and did you learn anything from it that you still use today?

02:34 Finding your organizational trigger words

08:41 Can you really change your company?

11:12 Most companies are more like gold rush towns than lasting institutions

15:26 Finding joy at work when the company won't love you back

18:29 Every leader is a game designer

21:45 Stepping back and seeing the system

27:55 Why chasing clarity at work might be the wrong goal

33:20 Having all the data and asking the wrong questions

35:34 How Dotwork is rethinking organizational strategy tools

40:42 Building flexible operating systems that leaders will actually use

44:14 Building a generalist career in a specialist world

50:21 Leave us a review and share the show with a friend

Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

You've done the hard work. Your team cracked the code on a new process/workflow/policy/design, your ways of working are genuinely better, and now...everyone else is actively uninterested. It's infuriating, and also completely predictable.

In this mini AUA, Rodney and Sam unpack why good ideas don't automatically spread in federated structures, from classic Not Invented Here syndrome to the underappreciated truth that you can't export a finished experience and skip the struggle. They make the case for becoming an internal consultant rather than an evangelist — offering scaffolding, not superiority.

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Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

Compensation is where human psychology and organizational systems collide—and in Part 1, Rodney and Sam named why it so often turns into a hedonic treadmill: every lever you pull to reduce dissatisfaction tends to raise expectations and create new dissatisfaction. If you haven’t listened to Part 1 yet, start there for the “why this is so messy” foundation.

In Part 2, Rodney and Sam move from diagnosis to design: what principles should a compensation system actually be built on—and what do you do next? They walk through practical comp first principles and explore concrete moves teams can experiment with—like simplifying comp, reducing negotiation, and creating healthier feedback loops.

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Mentioned references:


⁠"previous comp episode": AWWTR Ep. 45, Part 1

"JEDI": BNW Ep. 40 with Sharan Bal

"Midnight Zone": Depthfinding Miniseries

BNW Ep. 6 with Joel Gascoigne

BNW Ep. 36 with Nathan Barry

BNW Ep. 84 with David Buckmaster

BNW Ep. 89 with Nikki Kaufman

00:00 Intro: What Would You Rename Yourself?
03:26 Comp Principle #1: Pay and Human Dignity
07:21 Comp Principle #2: Pay Equity at Work
10:06 Comp Principle #3: Salary Clarity and Transparency
15:56 Comp Principle #4: Collective Alignment on Pay
19:04 Comp Principle #5: Employee Participation in Pay Decisions
21:47 Comp Principles #6 & #7: Simplicity and Talking About Pay Less
24:12 Redesign Idea #1: Anonymous Team Rewards Ranking
25:48 Redesign Idea #2: Eliminating Salary Negotiation
28:03 Redesign Idea #3: Interview Elsewhere to Reset Pay Expectations
29:38 Redesign Idea #4: Create Transparency for Employees
32:44 Outro: Rate the Podcast + Share At Work With The Ready

Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

Small doesn't mean simple. In fact, smaller organizations are often more complex in the ways that are hardest to manage — personalities loom larger, every conversation carries more weight, and the line between "business problem" and interpersonal drama gets uncomfortably thin.

In this mini AUA, Rodney and Sam break down why smaller orgs typically need to install minimum viable structure to tame the chaos — while larger orgs are usually trying to remove it. Same toolkit, opposite motion. They also explore the quiet inflection point that hits somewhere under 50 people, when "everyone knows everything" suddenly stops being true and no one quite knows what to do about it.

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Mentioned references:

"strategy": AWWTR Ep. 2

"principles-based budgeting"

Dunbar's number

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Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

Compensation is one of the messiest parts of any organization. Pay becomes a proxy for belonging, validation, performance, identity, and status… which means it’s almost guaranteed to feel unfair, confusing, and emotionally loaded. Layer on a capitalist “more is always better” mindset, and you get the hedonic treadmill of work: every raise increases expectations, which creates the next round of dissatisfaction.

In Part 1 of this two-part series on compensation, Rodney Evans and Sam Spurlin dig into why comp is so psychologically charged, why most systems are overly complex, and why the “objective” company lens will never fully match the lived human experience of money.

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Mentioned references:

baby hyenas

hedonic treadmill

performance management episode: AWWTR Ep. 39

"authority field": The Ready's OS Canvas

FAANG (Facebook, Amazon, Apple, Netflix, Google) aka "Big Tech"

EOT (Employee-Owned Trust)

00:00 Intro + Check-In: What’s the best animal you’ve seen recently?

04:07 The pattern: No level of compensation ever feels like enough.

10:17 Comp becomes a proxy for self-worth

14:16 Setting individual comp levels

23:23 Importance of real pay transparency, not “bands”

27:24 Comp “up and to the right” ignores market value

31:25 Setting team-level comp and rewards

36:04 Shared rewards vs Hunger Games for sales teams

38:29 Is equity a good thing…or a trap?

46:09 Wrap Up: Continued next time in part 2

Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.