33. What’s Your Type? The Enneagram at Work with Liz Orr

Producer Note: Hey there! We’re on vacation this week, but we didn’t want to leave your feed empty. Some of our most popular conversations this past year have been about the Midnight Zone and that’s why we’re sharing this fantastic episode from our friends over at Fixable. We hope it gives you some fresh strategies for navigating (and even embracing!) conflict in your organization, and we’ll see you next time. ------------------------- Most of us try to avoid conflict, particularly at work. But when done right, conflict can be a tool to strengthen interpersonal bonds and generate better results. In this episode, Anne and Frances team up with Amanda Ripley, global conflict journalist and author of the bestselling book High Conflict: Why We Get Trapped and How We Get Out. They tackle the missteps teams often make when it comes to handling conflict and provide actionable alternatives to foster healthy conflict habits in any organization. Follow Hosts: Anne Morriss (@annemorriss | LinkedIn: @anne-morriss), Frances Frei (@francesxfrei | LinkedIn: @francesfrei) Guest: Amanda Ripley (Instagram: @ripleywriter | Website: amandaripley.com/) Links https://anneandfrances.com/High Conflict: Why We Get Trapped and How We Get Out This episode originally aired on June 15, 2025.

Most of us think we know ourselves (and the people we work with) pretty well. But when tensions rise, deadlines loom, or feedback lands wrong, the truth comes out: we’re all running on a set of deep, often invisible patterns. What if we could see those patterns clearly, and choose something better? Enter the Enneagram: a framework that maps nine core motivations, survival strategies, and ways of seeing the world. This week, Rodney sits down with Liz Orr, author of The Unfiltered Enneagram and the voice behind Rude Ass Enneagram, to explore how this tool can help us understand ourselves, our teammates, and the hidden drivers behind workplace friction. From recognizing your own “midnight zone” work to navigating type-to-type dynamics, Liz shares practical insights for breaking unhelpful patterns, building trust, and working more compassionately with others. Learn more about Liz: On Instagram: @rudeassenneagram Read her book: The Unfiltered Enneagram -------------------------------- Let's work together: ⁠⁠⁠⁠⁠⁠https://www.theready.com/working-together⁠⁠⁠⁠⁠⁠ Get our newsletter: ⁠⁠⁠⁠⁠⁠Sign up here⁠⁠⁠⁠⁠⁠⁠⁠. Follow us: ⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠ -------------------------------- Mentioned references: Midnight Zone and Depthfinding Myers-Briggs DISC assessment Enneagram Type descriptions Enneagram Type combinations "the hero's journey" 00:00 Intro + Check-In: What would you be doing if it wasn’t this? 03:30 What is the Enneagram? 06:26 101 course on the Nine Types of the Enneagram 14:04 When your Type solidifies 15:15 Exploring Rodney’s Type as an example 20:44 How Types interact 23:19 Using the Enneagram to recognize and break your own patterns 26:54 Eights as leaders (CEOs, CFOs) tend to fight every battle 29:54 Debunking cultural gender stereotypes around the Enneagram 34:21 Understanding what we’re “getting” in return for our behavior 37:22 Navigating the cringe of self-compassion and forgiveness 44:59 Dealing with “therapy language performance” from friends and coworkers 48:03 The Enneagram’s role in the workplace 50:21 Overcoming the dismissal of “soft skills” and “soft power 52:50 Wrap up: Leave us a review and share the show with your coworkers! Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠.

In most companies, mergers and acquisitions (M&A) is treated like a finish line. But the truth is, signing the deal is just the start—and if you haven’t thought deeply about how two operating systems, cultures, and teams will actually work together, you’re already behind. The vast majority of M&A efforts fail to deliver long-term value, not because the deal was bad, but because the integration never really happened. This week, Rodney and Sam unpack why M&A is so alluring, so broken, and so often misunderstood. From boardroom incentives and CEO ego to missing strategy and magical thinking, they dig into what really drives the endless appetite for acquisition—and why the actual design work of merging two organizations is almost always underfunded, under-led, or completely ignored. -------------------------------- Let's work together: ⁠⁠⁠⁠⁠https://www.theready.com/working-together⁠⁠⁠⁠⁠ Get our newsletter: ⁠⁠⁠⁠⁠Sign up here⁠⁠⁠⁠⁠⁠⁠. Follow us: ⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠ -------------------------------- Mentioned references: "reorg ep": AWWTR Ep. 31 "70-75% of M&A fails" Ben Thompson and Stratechery AOL/Time Warner merger Microsoft/Nokia merger "LARPing" "OS work": The Ready's OS Canvas "Midnight Zone and Twilight Zone": The Ready's Depthfinding ecotones "Microsoft innovation" Rob Cross and Organizational Network Analysis (ONA) McChrystal Group mission-based team (MBT): FoHR Miniseries, Episode 1 00:00 Intro + Check-In: What is something you’ve done recently that seemed like a good idea but has since proven otherwise? 04:01 The Pattern: Companies acquire others for growth, merge goes bad, so have to acquire another 09:54 Big visible activities with very unclear ROI 14:09 Buying innovation because you can’t innovate internally 19:15 Destroying all the qualities that made the target company valuable 24:34 Mergers and acquisitions buy CEOs longer tenures 28:19 Our culture celebrates the big swings, not the steady transformation 30:35 Executive attention vanishes once the deal is signed, but that’s when the real work starts 38:43 Idea #1 - Let acquired company operate independently for as long as possible 41:35 Idea #2 - Use organizational network analysis to find and utilize your leverage points 44:14 Idea #3 - Spin up a real mission-based team around integration, or due diligence 46:18 Idea #4 - During due diligence, look at more than just the financial spreadsheets 47:08 Wrap up: Leave us a review and share the show with a friend! Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠.

It’s reorg season…again. And for many companies, it always is. Every 12 to 18 months, another wave of layoffs, leadership swaps, and org chart redraws rolls through the system. And yet, little changes. Strategy stalls. Trust erodes. Work doesn’t get better, just messier. So why do so many organizations keep reaching for the reorg lever first? This week, Rodney and Sam unpack the seductive logic (and systemic failure) of reorgs as a change strategy. They dig into why structure work always feels like the fastest, most visible move a leader can make and why it so rarely delivers. Along the way, they explore the very real fallout of these moves on culture, trust, and performance, and offer smarter starting points for those considering a shake-up. -------------------------------- Let's work together: ⁠⁠⁠⁠https://www.theready.com/working-together⁠⁠⁠⁠ Get our newsletter: ⁠⁠⁠⁠Sign up here⁠⁠⁠⁠⁠⁠. Follow us: ⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠ -------------------------------- Mentioned references: The Ready's OS Canvas "16% of reorgs deliver the expected value" Sunshine, Twilight, and Midnight Zones: The Ready's Depthfinding "layoffs episode": Brave New Work Ep. 152 Team Topologies, 2019 book by Matthew Skelton and Manuel Pais holacracy sociocracy "retention increase if you have a best friend at work" "new job is one of the most stressful life events": Holmes and Rahe stress scale, see combined score of “dismissal from work”, “change to different line of work”, and “Change in responsibilities at work” DAO Miniseries "Jeff Williams departure" "value flow mapping" Haier and micro-enterprises 00:00 Intro + Check-In: What feature is really important in your living space? 03:27 The Pattern: Orgs trapped in a cycle of endless reorgs 05:15 The fastest, most visible sign of change a CEO can show to a board or investors 09:55 Structure work should always come last, but most people do it first 12:22 Reorgs to hit a number come at the expense of workflow, culture, and strategy 19:07 Stop changing the structure without touching the ways of working 22:19 Fundamental components of structure work 25:14 How The Ready approached it’s own reorg 26:34 Fallout of bad reorgs on your team and culture 31:17 Companies underestimate the stress of reorgs on individuals 34:40 Hot takes: org structure in the age of AI; legal OS around restructuring 38:15 Idea 1: Use reorgs to recalibrate roles back to defaults 39:42 Idea 2: Value flow map your company before considering a standard reorg 42:53 Idea 3: Test new structure in parts of phases, not everything all at once 44:30 Idea 4: Accept that some centralization is required 47:50 Wrap up: Leave us a review and share the show with your coworkers! Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠.

The extended leadership team (those just below the C-suite) often finds itself stuck between translating strategy and triaging dysfunction. They’re tasked with cross-functional execution, but are rarely equipped, empowered, or aligned to pull it off. And in most organizations, this group is caught in a cycle of managing up, managing down, and managing chaos all around—with very little time or clarity left to lead. This week, Rodney and Sam take a closer look at what’s really going on with extended leadership teams, why they matter so much, and what gets in their way. From power dynamics and peer competition to vertical incentives and missing cross-functional glue, they pull apart the system that makes this group so hard to organize—and so critical to transformation. They also share field-tested tactics that can turn this underutilized layer into an OS-upgrading powerhouse. -------------------------------- Let's work together: ⁠⁠⁠https://www.theready.com/working-together⁠⁠⁠ Get our newsletter: ⁠⁠⁠Sign up here⁠⁠⁠⁠⁠. Follow us: ⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ -------------------------------- Mentioned references: Fruit Roll-Ups leadership teams org design ep: AWWTR Ep. 13 Sunshine Zone: Depthfinding Ep. 3 Basecamp (aka 37signals) and managers Haier and managers Twilight Zone: Depthfinding Ep. 4 mission-based teams (MBTs): FoHR Ep. 1 Jason Fried & "company as the product" 00:00 Intro + Check-In: What is one of your favorite low tech work hacks? 02:53 The Pattern: The extended leadership team is trapped between strategy and execution 05:17 The C-suite’s peace comes at the expense of chaos in the extended leadership team 09:04 Silos and competition between departments 12:52 Functions don’t truly understand what other functions contribute 15:40 The true work of the extended leadership team 21:40 External pressure on GenX and Millenial leaders reinforces the status quo 27:56 Idea 1: Identify shared purpose of your extended leadership team 30:45 Idea 2: Top missions for cross-functional leadership teams 35:21 Idea 3: Chartering a leadership team “role” for shared participation and ownership 37:52 Wrap up: Leave us a review and share the show with your colleagues Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠.

For years, the conversation around remote work has been stuck in binary debates. Home vs. office? Productivity vs. flexibility? Control vs. chaos? But what if we zoomed out and asked a better question: What kind of future is possible if people could actually work from anywhere? This week, Rodney and Sam sit down with Raj Choudhury (Harvard Business School professor and author of The World Is Your Office) to explore what happens when companies stop fixating on location and start designing for freedom, trust, and real human needs. From engineering serendipity to reimagining hybrid models, they unpack how truly distributed work changes everything: how we meet, how we lead, how we grow talent, and how we build a more equitable future. Learn more about Raj and his work by following him on LinkedIn and reading his new book: The World Is Your Office: How Work from Anywhere Boosts Talent, Productivity and Innovation. -------------------------------- Let's work together: ⁠⁠https://www.theready.com/working-together⁠⁠ Get our newsletter: ⁠⁠Sign up here⁠⁠⁠⁠. Follow us: ⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠ ⁠⁠⁠⁠Instagram⁠⁠⁠⁠ -------------------------------- Mentioned References: US Patent Office study TEAPP (Telework Enhancement Act Pilot Program) Sid Sijbrandij and GitHub episode: BNW Ep. 35 Darren Murph The Allen curve homophily Tulsa Remote Zapier and "Wade Bot" algorithm aversion 00:00 Intro + Check-In: What’s your favorite aspect of being able to work from anywhere? 03:49 Central focus: How do organizations access distant talent? 08:20 How work from anywhere is different from work from home 11:08 Rethinking in-person days 19:23 The data doesn’t support RTO mandates 24:13 Dispelling productivity concerns 27:15 Unlocking digital twins in the workplace 34:05 Small towns being competitive for talent 38:04 AI’s role in work from anywhere 45:09 Where to look ahead for the next 5 years 47:10 Wrap up: Leave us a review and share this show with a coworker! Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠.

In a year marked by tighter budgets, leaner teams, and growing uncertainty, more organizations than ever are choosing to go it alone. DIY transformation feels safer, cheaper, more in control. But that instinct to do more with less is often the very thing that stalls progress. Because without the right structure, support, and space, most internal change efforts don’t just slow down… they spin out. This week, Rodney and Sam pull apart the decision to “DIY” major organizational change. They explore why so many teams default to doing it themselves, what makes internal transformation efforts so hard to sustain, and the subtle power dynamics that turn strategic remits into order-taking. Along the way, they dig into what it really takes to get change moving—from alone on the inside or with a partner. -------------------------------- Let's work together: ⁠https://www.theready.com/working-together⁠ Get our newsletter: ⁠Sign up here⁠⁠⁠. Follow us: ⁠⁠⁠LinkedIn⁠⁠⁠ ⁠⁠⁠Instagram⁠⁠⁠ -------------------------------- Mentioned references: Ayurvedic eating RACI episode: AWWTR Ep. 10 Bill Anderson episode: Brave New Work 68 The Ready's Tension and Practice Cards The Ready's OS Canvas Future of HR model Rodney's problem solution fit article 00:00 Intro + Check-In: What is a DIY victory or failure you’ve had recently? 03:51 The Pattern: DIY Transformation tends to be “try, fail, repeat” 05:27 Why people decide to DIY change work 11:40 Orgs are designed to fight change 15:32 The deck is stacked against internal OD/OE/transformation teams 19:43 You don’t know what you don’t know 23:43 Challenges of trying to change your coworkers 27:00 Lack of authority and power kneecap real progress 32:10 Hidden financial and org costs of DIY change 37:44 Idea 1: Contract for a CLEAR remit, REAL customer discovery, and actual solution design 42:35 Idea 2: Don’t start with the whole project, start with a smaller leverage point 44:59 Wrap up: Leave us a review and share the show with your coworkers! Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠.

We talk a lot about doing less to get more—but in practice, most organizations end up doing the opposite. When priorities pile up, and nothing gets removed or finished, the result is a familiar kind of chaos: too many projects, too little focus, and an endless loop of adding more in hopes of getting unstuck. This week, Rodney Evans and Sam Spurlin unpack one of the most common organizational dynamics they see: the “more-is-more” trap of priority overload. They dig into why deprioritizing anything at work feels so psychologically and politically fraught, how identity and sunk costs keep teams clinging to low-impact efforts, and ways for leadership teams to prioritize at a org wide level, not just assemble a laundry list of everyone’s pet projects. -------------------------------- Ready to start changing your organization? Let's talk! https://www.theready.com/working-together Want future of work insights and experiments you can try delivered to your inbox? ⁠⁠Sign up here⁠⁠. Follow us on your favorite platforms for more org design nerdery: ⁠⁠LinkedIn⁠⁠ ⁠⁠Instagram⁠⁠ -------------------------------- Mentioned references: "60% of Americans" Depthfinding John Cutler's prioritization article WSJF (weighted-shortest-job-first) GTD: Brave New Work Ep. 39 with David Allen 00:00 Intro + Check-In: What’s a molehill you’re willing to defend until the end? 03:52 The Pattern: We prioritize everything and nothing gets done 06:01 John Cutler’s 4 Jobs of Prioritization 10:08 Why it’s so hard to stop doing lower value things 18:35 Difference altitudes of priorities 22:23 Where leaders mess up prioritization 25:11 Continuous steering version of priorities 33:05 Idea 1: Use a variant of WSJF for your own variables 37:21 Idea 2: Shift from saying “no” to “not right now” 39:27 Idea 3: Visualize your work to “see” deprioritization 41:26 Idea 4: Openly talk about conflicting priorities 44:00 Wrap up: Share the show with your coworkers! Sound engineering and design by Taylor Marvin of ⁠⁠⁠Coupe Studios⁠⁠⁠.

Despite an explosion of frameworks, toolkits, and “best practices,” the success rate of organizational change hasn’t improved in over a decade. For all the decks, comms plans, and transformation initiatives being sold, most companies still find themselves stuck, repeating the same plays and hoping for different results. This week, Rodney Evans welcomes back Michael Bungay Stanier—best-selling author, host of the new podcast Change Signal, and longtime friend of the show—who’s on a mission to cut through the noise and find what actually works. They explore why change still feels so weird, the real leverage points for shifting individual and organizational behavior, and whether it’s finally time to retire “change management” as we know it. Get a copy of Michael's change quadrants he talks about in this episode here: Michael's quadrants. Learn more about Michael: Follow him on LinkedIn Listen to his podcast, Change Signal. Subscribe to his newsletter, The Change Signal. Check out his website, MBS.works See his two prior appearances on our show, BNW Ep. 19 and BNW Ep. 75. -------------------------------- Ready to start changing your organization? Let's talk! ⁠https://www.theready.com/working-together⁠ Want future of work insights and experiments you can try delivered to your inbox? ⁠Sign up here⁠. Follow us on your favorite platforms for more org design nerdery: ⁠LinkedIn⁠ ⁠Instagram⁠ -------------------------------- Mentioned references: Jason Fox's episode: AWWTR Ep. 17 John Kotter and the 8 Steps Depthfinding and the "Zones" Ron Heifetz Immunity to Change, book by Robert Kegan and Lisa Lahey Peter Block Winston Churchill "We Shape Our Buildings" Maslow's hierarchy of needs Larissa Conte: BNW Ep. 151 Katie Milkman: Change Signal Ep. 2 Caroline Webb: Change Signal Ep. 5 Timestamps: 00:00 Intro + Check-In: Do you have a non-work related goal that you’re working towards right now? 9:59 Michael’s journey to un-weird change 14:49 Michael’s individual and organizational unlocks for change 21:24 Importance of strong foundational habits to succeed in change work 25:37 Understanding of power dynamics in change work 33:27 Outdated change mindsets to let go of 38:38 Rodney and Michael’s takeaways 40:28 Wrap up: Leave us a review and share the show with your coworkers! Sound engineering and design by Taylor Marvin of ⁠⁠Coupe Studios⁠⁠.

In this miniseries, we’re exploring Depthfinding—an easy-to-grasp framework designed to help leaders and teams solve their gnarliest cross-functional challenges. This week, Rodney and Sam reflect on what they’ve learned over the course of this eight-part miniseries—about the framework, their own Midnight Zones, and what it means to navigate complexity amidst uncertainty. They share how their thinking has evolved since launching the series, when Depthfinding is most useful (and when it’s not), and why every organization eventually has to ask: Who are we designing for? The end of the miniseries isn’t the end of Depthfinding. Now it’s time for you to dive in. Download the Depthfinding guide⁠ to get the template and examples of how to use it. Want to learn more about Depthfinding? Head here: ⁠theready.com/depthfinding⁠ -------------------------------- Want future of work insights and experiments you can try delivered to your inbox? ⁠Sign up here⁠. Follow us on your favorite platforms for more org design nerdery: ⁠LinkedIn⁠ ⁠Instagram⁠ -------------------------------- Mentioned references: Bob Vila The Ready's OS Canvas "strategy pancakes": AWWTR Ep. 2 "even/overs": BNW Ep. 44 "op rhythm": BNW Ep. 118 Yaggadang by BG & Coyote Radio 00:00 Intro + Check-In: What is the warning label on the back of your box? 04:26 Depthfinding’s impact on our work 08:19 New discoveries from the miniseries 13:50 Limitations of Depthfinding 16:34 Troubleshooting consultants stuck in one zone 22:14 What’s next for Depthfinding 25:14 What’s next for the podcast 27:11 Wrap up: Leave us a review and share the show with your colleagues This episode's theme music is ⁠Yaggadang by BG & Coyote Radio⁠. Sound engineering and design by Taylor Marvin of ⁠Coupe Studios⁠.