Episodios

  • 46. Embracing the Beautiful Mess: How Organizations Actually Work with John Cutler

    46. Embracing the Beautiful Mess: How Organizations Actually Work with John Cutler
    Apr 6 2026
    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 -------------------------------- Ready to change your organization? ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Let's talk.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Get our newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Sign up here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow us: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -------------------------------- 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.
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    52 m
  • AUA: Why Won't The Rest Of The Org Copy What’s Working?

    AUA: Why Won't The Rest Of The Org Copy What’s Working?
    Mar 30 2026
    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. -------------------------------- Ready to change your organization? ⁠⁠⁠⁠⁠⁠⁠Let's talk!⁠⁠⁠⁠⁠⁠⁠ Get our newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Sign up here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Follow us: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -------------------------------- Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.
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    9 m
  • 45, Part 2. Why Pay Will Never Feel Fair At Work (And It's Not The Money)

    45, Part 2. Why Pay Will Never Feel Fair At Work (And It's Not The Money)
    Mar 23 2026
    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. -------------------------------- Ready to change your organization? ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Let's talk.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Get our newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Sign up here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow us: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -------------------------------- 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.
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    34 m
  • AUA: Why Is My Small Org So Hard To Run?

    AUA: Why Is My Small Org So Hard To Run?
    Mar 16 2026
    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. -------------------------------- Ready to change your organization? ⁠⁠⁠⁠⁠⁠⁠Let's talk!⁠⁠⁠⁠⁠⁠⁠ Get our newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Sign up here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Follow us: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -------------------------------- Mentioned references: "strategy": AWWTR Ep. 2 "principles-based budgeting" Dunbar's number -------------------------------- Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.
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    6 m
  • 45, Part 1. Why Pay Will Never Feel Fair At Work (And It's Not The Money)

    45, Part 1. Why Pay Will Never Feel Fair At Work (And It's Not The Money)
    Mar 9 2026
    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. -------------------------------- Ready to change your organization? ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Let's talk.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Get our newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Sign up here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow us: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -------------------------------- 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.
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    48 m
  • AUA: What Should L&D Do About AI Right Now?

    AUA: What Should L&D Do About AI Right Now?
    Mar 2 2026
    AI pressure is landing squarely on Learning & Development teams. Execs want “future skills”…yesterday. The tension? How do you stop churning out more courses and start building real capabilities in the age of AI? In this AUA mini episode, Rodney and Sam share the first moves they’d make if they were leading L&D right now. From getting hands-on with workflow automation tools to shifting from tool training toward systems thinking and experimentation, they outline how L&D can move from reactive skill provider to strategic capability builder. Want to build skills like this to help your team succeed in 2026? Learn about our Capability Catalyst program: https://hubs.la/Q040ccYF0 -------------------------------- Ready to change your organization? ⁠⁠⁠⁠⁠⁠Let's talk!⁠⁠⁠⁠⁠⁠ Get our newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Sign up here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Follow us: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -------------------------------- Mentioned references: recent change skills episode: AWWTR Ep. 42 Relay n8n Ethan Mollick Greg Shove: AWWTR Ep. 41 Scott Galloway Chase Adams EvolvingAI Morning Brew -------------------------------- Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.
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    7 m
  • 44. Forget ROI: The Ethical Case for Org Design

    44. Forget ROI: The Ethical Case for Org Design
    Feb 23 2026
    Most org design conversations get forced through a narrow funnel: prove the ROI, justify the spend, make the numbers work. But if work is something most people can’t opt out of—and where we spend a huge chunk of our attention and waking lives—then “it pays off” feels like a painfully small standard. This week, Rodney and Sam explore the ethical case for organizational design. They move beyond spreadsheets and profit metrics to ask bigger questions about leadership, power, transparency, compensation, and the human impact of broken systems. What do organizations owe the people who work inside them? Is better workplace design a moral responsibility — not just a financial strategy? -------------------------------- Ready to change your organization? ⁠⁠⁠⁠⁠⁠⁠⁠⁠Let's talk.⁠⁠⁠⁠⁠⁠⁠⁠⁠ Get our newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Sign up here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow us: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -------------------------------- Mentioned references: r/antiwork Mihaly Csikzentmihalyi and Flow Target CEO comp package (note: New CEO’s comp package is roughly $16m, vs over $70m for the prior CEO in 2020) triple bottom line John Rawls and A Theory of Justice 00:00 Check-In: What’s your energy like right now? 04:04 Divorcing doing what’s “good work” from ROI 08:16 A “good” experience is the exception rather than the rule 10:06 Protecting yourself isn’t “selling out” 15:41 Spending our attention on worthy things 21:35 Leadership vs. worker power disparity is broken 27:31 Ethically designed companies never are publicly traded 31:07 Principles and values of ethical orgs 40:35 Joy at work shouldn’t be nickled and dimed 44:35 Idea 1: Don’t accept performative change initiatives 47:17 Idea 2: Audit your existing principles and values 48:35 Idea 3: Don’t let leadership gaslight you into conforming 50:33 Wrap up: Leave us a review and share the show with a friend Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.
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    52 m
  • AUA: Can You Change an Org When Leadership Doesn’t See the Problem?

    AUA: Can You Change an Org When Leadership Doesn’t See the Problem?
    Feb 16 2026
    When the people at the center of power feel well-served by the current system, how do you create change? This week’s listener question gets at a frustrating reality: sometimes the OS is optimized for the very people you’d need to convince. The business is growing, shareholders are happy, and the executives at the top don’t feel the friction you’re experiencing. Add geography, hierarchy, and distance from decision-makers, and it can feel impossible to generate momentum from the edges. In this mini AUA episode, Rodney and Sam get honest about what’s actually within your control, and when it’s worth accepting that you won’t move the center—and when it’s smarter to redirect your energy toward the surface area you can influence. -------------------------------- Ready to change your organization? ⁠⁠⁠⁠⁠Let's talk!⁠⁠⁠⁠⁠ Get our newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Sign up here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Follow us: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -------------------------------- Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.
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    8 m