Tentacles - the podcast from Crown & Reach

Tom Kerwin
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Hi, we’re Tom and Corissa from Crown & Reach, and this is Tentacles. With over 100 episodes behind us, this might just be the best bad podcast out there. Unfiltered, unedited, and deeply curious. We talk strategy, sense-making, and the blurry edges between work and the rest of life — because sometimes, the only way through the fog is to feel your way forward, limbs outstretched. While we're migrating podcasts across, you can find all the goodness from our first 100 or so episodes here: https://shows.acast.com/triggerstrategy Hosted on Acast. See acast.com/privacy for more information.

  1. 3D AGO

    137: The six or seven problem when "being more strategic"

    Being strategic sounds like it should be serious business. It turns out the seriousness can be exactly what gets in the way. Following on from episode 136, Tom and Corissa pick up a listener thread about strategy being a zero-sum status game at the company level — then take a sharp left turn into why most people are stuck in exactly the wrong zone for doing anything useful with uncertainty. The conversation weaves together Lindy Hop, improv theatre, Pitch Provocations, and a fairly bleak observation about time — into something unexpectedly practical. The barbell approach to play: why chronic 6/7 stress is actually the worst place to be for innovation, and what the 0 and 10 extremes have in commonWhy "just be more playful" is almost as useless as "just be more strategic" — and practical stuff you can do insteadUncertainty bubbles: how to artificially impose the right kind of pressure so that different things can emergeFront-loading the nightmare — and why Pitch Provocations deliberately generates high-signal feedback when everything is still wrongThe hidden cost of over-investing before you've tested: stress that balloons, sunk costs, and projects that polish the wrong thingWhy improv, Lindy Hop, and safe-to-fail experiments are the same muscle — and how to build it somewhere low-stakes firstStrategy as fractal: you don't need "strategy" in your job title to be doing more of it right now For anyone who suspects the rules they're playing by are made up — and wants somewhere safe to test that hypothesis. Drop us a line: tentacles@crownandreach.com References and links: Episode 136: When they tell you to 'be more strategic' (but not what that actually means) https://shows.acast.com/tentacles/episodes/698de53934f221647e8927eaDonald Cox – friend of Tentacles who shared the point that there's only a little strategy at any one time at the company levelViktor Frankl — Man's Search for MeaningDave Snowden — stress, innovation, and exaptationMemento MoriInternal locus of controlPitch Provocations method (episodes 007–009 for intro)Uncertainty bubbles — Crown & Reach concept, find out more when we share at https://reach.crownandreach.comMultiverse Mapping — https://multiversemapping.comAngie Lina — improv teacher and strategy/sense-making practitioner, former LSE Lindy Hop studentFind out more about us and our work at crownandreach.com Hosted on Acast. See acast.com/privacy for more information.

    28 min

  2. FEB 12

    136: When they tell you to "be more strategic" (but not what that actually means)

    When your boss tells you to "be more strategic," what do they actually mean? Sometimes it's genuine - they see you working hard on the wrong things and want to help you refocus. Sometimes it's politics - they need you to read between the lines they can't legally spell out. And sometimes it's just offloading risk. The problem? You're supposed to figure out which story is true, and then what to do about it, with no guidance and zero training budget. In this episode, we walk (literally - five-months-pregnant Corissa sets the pace) through the murky reality of being told to level up without a map. We explore why "strategic" is a suitcase word people pack with whatever they like, how to decode what's actually being prioritised vs. what's officially important, and a simple framework you can use today to start getting better signal from your manager. Including-but-not-limited-to: Why "be more strategic" often secretly means "be more politically savvy" (and what to do about that)The official game vs. the real game - and how to play both without burning outSignal > Stories > Options: how telling yourself different stories unlocks different actionsContext, Proposition, Triggers (CPT) - a back-briefing technique that helps you test assumptions and get clearer directionWhy diligent people can get penalised for doing exactly what the organisation says it wantsWhen half-arsing the official work is actually the strategic move This one's for anyone who's doing good work, getting mixed signals, and wondering why their effort isn't translating into recognition or progress. Drop us a line with your own "be more strategic" stories: tentacles@crownandreach.com References and linky goodness: John Grant (labour market researcher, Cynefin Slack community member)Dave SnowdenStealing the Corner Office by Brendan ReidSignal > Stories > Options framework (Crown & Reach) https://triggerstrategy.substack.com/p/signals-stories-optionsContext, Proposition, Triggers (CPT) https://reach.crownandreach.com/posts/mini-pitchesMultiverse Mapping: https://multiversemapping.comPitch Provocations method (referenced, episodes 007-009): https://shows.acast.com/triggerstrategyCynefin Co's upcoming training (covers all seven frameworks including Estuarine Mapping) https://thecynefin.co/product/masterclass-7-frameworks-uk-2026-2/ Find out more about us and our work at crownandreach.com Hosted on Acast. See acast.com/privacy for more information.

    33 min

  3. FEB 6

    135: The resistance to instability - and why Stewart Lee hasn't finished his show yet

    What does a comedian's unfinished show, a five-year plan gathering dust, and your CEO's quiet plea to "go back to normal" have in common? They're all wrestling with the sense that eventually, things will settle down, right? That the chaos is only temporary. That once this transformation/restructure/market shift is done, we can finally get back to business as usual. In this one, with plenty of traditional traffic noise and some moments of getting lost, we start off with the Stewart Lee gig we went to last night, move through organisational transformation war stories, and end up at Estuarine Mapping – a method for navigating strategy when your substrate keeps shifting beneath you. Including-but-not-limited-to: Why the most dangerous person in the room is the one waiting for certainty to returnThe CEO confession that reveals what most executives are actually thinking during transformationWhat happens when you're getting your product (show, strategy, service, ...) ready in the way that normally works ... but the context keeps changingSubstrate, salt marshes, and granite cliffs: why your strategic estuary has different pace layers (and how to tell them apart)The counterintuitive move that matters way more than better planningWhy accepting that things won't settle is weirdly when things can start to shift for you This one's for anyone who's ready to stop waiting for things to calm down already. References Ben Sauer https://bensauer.net/Stewart Lee https://www.stewartlee.co.uk/Dishoom https://www.dishoom.com/Estuarine Mapping https://reach.crownandreach.com/posts/a-trip-into-the-estuary Find out more about us and our work at crownandreach.com Hosted on Acast. See acast.com/privacy for more information.

    23 min

  4. JAN 20

    134: The Protocol Problem part 1 – Geoff's shadow spreadsheet sprawl

    "Geoff" has been running critical parts of every business on a Byzantine spreadsheet empire for 20 years. Every IT department wants to regulate him. Who's right? (Trick question: you need both.) In this episode, we feel our way through the murky territory of protocols—from life-saving surgical checklists to shadow IT empires built by people like Geoff, who just want to get their jobs done without asking permission. What we discovered: protocols aren't the enemy. Neither are the people who break them. You need both, and—whether you like it or not—you're going to get both anyway. Fascinations: Why giving someone just enough control over how they wash dishes is a vital part of managementThe novel "tracer dye" method for tracking shadow IT (and why Geoff will quickly find a way around it)How a 19th-century doctor was ejected from the medical community for [gasp!] suggesting surgeons wash their handsHow expert oil rig workers can land helicopters in storms through tacit knowledge no checklist could captureThe difference between a checklist, a flow chart, and knowing when neither will save youHow social norms function as soft protocols (and why London Tube etiquette is more fragile than you think) This one's for anyone who's ever tried to bring order to chaos — and for anyone resisting someone else's attempt to do the same. Links and references Venkatesh Rao – "Summer of Protocols" / protocolization conceptVaughn Tan – "boring tiny tools" concept https://vaughntan.org/bttparadigmIgnaz Semmelweis – 19th-century physician who pioneered handwashingAtul Gawande – Author of The Checklist ManifestoDave Snowden – Cynefin framework / oil rig helicopter storyGary Klein – Expert intuition and pattern recognitionProcrustes – Greek mythology (innkeeper with the "one-size-fits-all" bed)Chick sexing – Example of tacit knowledge that can't be articulatedSocial protocols – Norms like cheek-kissing customs across culturesSimple Mail Transfer Protocol (SMTP) / Hypertext Transfer Protocol (HTTP) – Technical protocol examples Find out more about us and our work at crownandreach.com Hosted on Acast. See acast.com/privacy for more information.

    30 min

  5. JAN 16

    133: Giant hats and fluffy aspirations - a year in review

    At the start of 2025, we faced a question: should we pack in our business and get [gasp] proper jobs? Our old brand felt like rotten decking – layers of horrible surprises with no clear foundation. But instead of quitting, we found an octopus, embraced distinctiveness over differentiation, and built something we're actually excited about. In this year-in-review, we trace a tangled thread from near-shutdown to genuine transformation, exploring what worked (uncertainty bubbles, relationship-driven growth, really good sandwiches) and what didn't (cold outreach, content marketing as a silver bullet, biscuits). Along the way, we workshop potential themes for 2026: bubbles, relationships, or possibly giant fluffy hats. Including but not limited to: Why Byron Sharp's evidence-based marketing vindicated our octopus obsession (distinctiveness > differentiation)The brutal realisation: thought leadership doesn't automatically convert to clients ... so what does?"The only thing worse than having a struggling business is having a successful business that you hate running"How our iterative approach to website messaging revealed insights no "big bang rebrand" could surface"Uncertainty bubbles" - presenting external certainty while protecting internal space for emergenceWhy we'll never do much cold outreach, even though it works for others, and what we're doing insteadThe hot seat moment that changed Tom's career: when someone just picked up the phone instead of planning This one's for anyone building something that doesn't quite fit the playbook, wondering whether there's a way to grow without becoming someone you don't recognise. Links and references: Byron Sharp (marketing researcher, Ehrenberg-Bass Institute)Dolly Parton: "Figure out who you are and then do it on purpose"Adrian Tchaikovsky (author, Children of Ruin - source of crown & reach octopus metaphor)Ehrenberg-Bass Institute (evidence-based marketing research)Distinctiveness vs differentiation (branding principle)Uncertainty bubbles (concept from Tom's Deel masterclass)Safe-to-fail probes (complexity/Cynefin principle)4U Framework: Unpack, Undergo and Unfold UncertaintyGranularity, disintermediation and iteration (our hidden facilitation principles)Innovation Tactics (Tom's Pip Decks card deck - 50+ methods) https://collabs.shop/yxzsjgDecking metaphor episode (our previous year-in-review) What's your theme for the year? Did anything in this episode trigger a thought for you? tentacles@crownandreach.com Find out more about us and our work at crownandreach.com Hosted on Acast. See acast.com/privacy for more information.

    38 min

  6. JAN 15

    132: Skate where the poke is going

    What if the reason you can't find the right name for your experiments is because you're asking the wrong question? In this one, we tackle a deceptively simple question from friend-of-Tentacles Matti about behavioural scientists, voting SMS messages, and which Cynefin domain they're playing in. This spirals into a wonderfully messy exploration of why simulation has limits, why "safe to fail" needs better words, and what ice hockey can teach us about working in uncertainty. Including-but-not-limited-to: Why the person who thinks they can predict things in complexity is the most wrong of allAn ice hockey metaphor that might finally make Cynefin dynamics click (featuring goosebumps, but not just because it's cold)How Multiverse Mapping deploys simulation for coherence testing, not fortune tellingThe liminal zone between complicated and complex – and why most "experiments" live thereWhy you can't measure a system without changing itThe profound difference between "conditions and consequences" vs "cause and effect" thinkingWhy "poking reality" might be better than probes, scouts, or bets (or why we still can't decide) This one's for anyone who's tired of treating complex human behaviour like it's a physics problem – and anyone who's wondered why their "experiments" keep failing even though the logic seemed sound. Links and references: Matti J Heino (posed the question about voting SMS)Dave Snowden (Cynefin framework, Ritual Dissent)Jen Briselli (ice hockey player and fellow complexity wonk) https://medium.com/topology-insight/head-up-feet-moving-b56e60867190Wayne Gretzky (Canadian hockey player, "skate where the puck is going" quote)Ursula Le Guin (author, Earthsea series, concept of "true names")Sun Tzu (conditions and consequences thinking)Cynefin Dynamics https://cynefin.io/wiki/Cynefin_DynamicsLiminal Cynefin https://cynefin.io/wiki/Cynefin_DomainsTom's bounded applicability diagram https://triggerstrategy.com/pitch-provocationsMultiverse Mapping: https://multiversemapping.comMatthew principle / Matthew Effect ("to him that has riches, more will come")Schrodinger's cat / superpositionEpisode 131: Safe to Fail Boops: A Pragmatic Critique of Business Experimentation (mentioned as previous episode)Why Does the Pedlar Sing? (on advertising, branding, and fame)Find out more about us and our work at crownandreach.com Hosted on Acast. See acast.com/privacy for more information.

    46 min

  7. JAN 13

    131: Safe-to-fail boops – a pragmatic critique of pseudo-scientific business experiments

    Jeff Bezos famously said not to overthink decisions you can just undo. But what if rolling back a change doesn't actually roll anything back? Tom and Corissa explore what can happen when you stack "reversible" experiments until the whole system collapses—from Facebook's slow degradation to an apocryphal Tesco story where undoing an experiment didn't fix what got broken. Along the way: sand pile criticality that can't be predicted, seaside penny waterfalls that cascade unpredictably, and why "safe-to-fail probes" might need a rebrand (spoiler: aliens). Including but not limited to: ● The grain of sand you can't predict—and why that matters for your business experiments ● When Subway cancelled unlimited salad and what it has in common with private equity acquisitions ● The Tesco experiment that broke the camel's back ● Throwing gravel from a boat in a storm ● Three of the requirements for truly safe-to-fail experiments (and why most companies miss all three) ● Boops vs. probes: finding language for experimentation that doesn't sound like something unpleasant that happens during an alien abduction This one goes out to all our friends who suspect their "data-driven" culture is just pretending to control things it can't. References: ● Jeff Bezos (Come on Jeff, get 'em!) – two-way door decisions concept ● Heraclitus – "you can't step in the same river twice" ● Sand pile and criticality (mathematical concept) ● The Sorites Paradox – when does some sand become a pile of sand? ● Enshittification – term and concept from Cory Doctorow ● Rory Sutherland – restaurant story about private equity "meaner" portions ● Tesco AB testing story (flagged as potentially apocryphal) ● Dave Snowden – Cynefin framework and safe-to-fail probes ● Path dependency (mentioned as topic of previous episode) ● North Star metrics ● Andrew Anderson – obliquely referenced in context of experimentation https://testingdiscipline.com/ Questions, stories, or better names for "safe-to-fail boops"? Email us: tentacles@crownandreach.com Find out more about us and our work at crownandreach.com Hosted on Acast. See acast.com/privacy for more information.

    27 min

  8. JAN 9

    130: The Sinclair Effect and the Winkler Constraint

    Upton Sinclair said "It is difficult to get a man to understand something when his salary depends on his not understanding it." But what if it goes deeper than salary? What if it's about identity itself? In this one, we explore why clear explanations often increase resistance, how an interior designer accidentally solved the change management problem, and what executive data analysis reveals when everyone plots different insights from the same numbers. From expert panels to Pimlico plumbers, we feel our way through the murky challenge of introducing ideas that threaten people's fundamental worldview – and discover that experience beats explanation every time. We get into: The Sinclair Effect: when understanding threatens identity (not just salary)Why simplifying your explanation can actually make your ideas MORE threateningThe executive data exercise that exposed beautiful chaos (everyone saw something different)The Winkler Constraint: how Caroline Winkler transformed her viewers' rooms with only three purchases allowed – and whyHow expertise shows up best under tight limitationsThe plumber parallel and why end customers don't care which wrench you useLeading with theory vs. leading with experience (and Tom's early mistakes)Opening portals vs planting flags, and the role of jammingWhy the saying "consistency is the hobgoblin of small minds" can hurt your career (ask us how we know)How to give people what they want while accidentally also giving them what they need (but without being manipulative about it) "You can't just not give people what they want. Then you are a blocker." References & links Upton Sinclair - "It is difficult to get a man to understand something when his salary depends on his not understanding it"Jen Briselli and Kyle Godbey's "Field notes from the swamp" https://youtube.com/playlist?list=PL89SttTTcPTGDdRlcQTcEqz4Ra9z2w0le&si=FC6O6zfbLCzykKm8Cynefin framework / complexity science (Dave Snowden)Caroline Winkler - YouTube interior designer https://youtu.be/ZvHM_VCybN0?si=CIPObJld8IM4Mc-XVenkatesh Rao - "Portals and flags" concept https://www.ribbonfarm.com/2014/06/25/portals-and-flags/Eleanor Roosevelt - (possibly apocryphal) "Consistency is the hobgoblin of small minds"Pivot Triggers (Crown & Reach) When have you fallen over by leading with theory? When have you enabled an experience that let things shift by themselves? Drop us a line: tentacles@crownandreach.com Find out more about us and our work at crownandreach.com Hosted on Acast. See acast.com/privacy for more information.

    29 min
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About

Hi, we’re Tom and Corissa from Crown & Reach, and this is Tentacles. With over 100 episodes behind us, this might just be the best bad podcast out there. Unfiltered, unedited, and deeply curious. We talk strategy, sense-making, and the blurry edges between work and the rest of life — because sometimes, the only way through the fog is to feel your way forward, limbs outstretched. While we're migrating podcasts across, you can find all the goodness from our first 100 or so episodes here: https://shows.acast.com/triggerstrategy Hosted on Acast. See acast.com/privacy for more information.

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