At Work with The Ready

• 30. Extended Leadership Teams: Set Up to Fail Yet Expected to Lead

  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.

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• 29. Working from Anywhere with Raj Choudhury

  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.

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• 28. DIY or DOA? Why Org Change Needs Outside Help

  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.

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• 27. Everything Can't Be Priority One

  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.

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• 26. Unweirding Change with Michael Bungay Stanier

  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.

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