When a hiring manager asks an unanswerable question, what if that's the whole point?

In this one, Corissa brings along a Reddit thread that stopped her in her tracks. A candidate who discovered, mid-interview, that the interviewer had never once rejected someone based on their actual answer. What they were watching for was whether you'd sit with the discomfort of having no right option, or immediately reach for a safe response ... one where you try to please the interviewer.

That question spirals us into the Kobayashi Maru, the art of giving feedback (and filtering feedback), why founders hold back from the conversations that would actually tell them the truth, and what it means to stop preparing the right answers and start trusting your own judgement.

• The Star Trek test designed to be unwinnable — and the eejit who won anyway
• Why the interviewer never rejects based on the answer itself
• The golden rule for making sense of feedback that's almost always true
• Why founders often make every move except the one that would actually test the idea
• Why when you hear "other people would ..." it should set off alarm bells
• The Red Queen effect in interviews: why every clever question eventually gets gameable
• How to prepare for interviews by stopping preparing for interviews

This one's for anyone who's noticed that the world keeps getting less predictable, and that "sitting with discomfort" is somehow both obvious advice and surprisingly hard to take.

References

• The Iron Triangle (good / cheap / fast ... pick two)
• Mike Haber's Inverted Iron Triangle (bad / late / over-budget ... you can have all three!)
• Neil Gaiman's feedback rule (attributed, then immediately un-attributed, could be apocryphal)
• Star Trek's Kobayashi Maru scenario
• The Red Queen Effect

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Everyone's got a brilliant value proposition. And most of them fail.

Tom's been reading a book that argues the problem isn't your messaging, your features, or your market research. The problem is that most people — most of the time — simply don't care.

Indifference is the default. And you can't overcome indifference by being more persuasive. (Nor by shipping faster, dear LLM code wrangling friends.)

In this one, we dig into why "unmet needs" is a nearly useless frame, what authentic demand actually looks like in the wild, and how a trucking startup found the wrong signal in all the right places.

• The "not-not" principle: why "it would be nice" is almost worthless, and what you're actually hunting for
• Why a massive client said "when can it be ready?", started talking money, all the signals you'd be excited about ... and still never signed the contract
• Our old buddy Ignatz Semmelweis. He was right in a way that was socially unacceptable, and so he was thrown out of the establishment. 50 years later, everyone else finally got it, but only because it became socially unacceptable not to.
• What six weeks of not talking to truckers reveals about the psychology of founders (and possibly all of us)
• An example based on a fish finder and an accidental twist that created a breakthrough in product demand, from meh to three or four on each boat.
• Sturgeon's Law, the Mom Test, and why all the right signals can still point you in the wrong direction

This one's for anyone who's built something sensible that people said they wanted — and then didn't buy.

References

• Heart of Innovation — Merrick Furst, Matt Chanoff, Daniel Sabbah & Mark Wegman (founders of Damballa and Flashpoint incubator) http://theheartofinnovationbook.com/
• Cedric Chin's writing on Heart of Innovation — https://commoncog.com/the-heart-of-innovation-why-startups-fail/
• Rob Fitzpatrick — Write Useful Books — https://writeusefulbooks.com
• Sturgeon's Law — https://en.wikipedia.org/wiki/Sturgeon%27s_law
• Goodhart's Law / Strathern's reframing — https://en.wikipedia.org/wiki/Goodhart%27s_law
• The Mom Test — Rob Fitzpatrick — https://www.momtestbook.com
• Innovation Tactics (Tom's card deck via Pip Decks) — https://pipdecks.com/products/innovation-tactics
• Multiverse Mapping — https://multiversemapping.com

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Your hospital has a brilliant new security measure. Your doctors have a paper cup.

Your IT team demands a new password every fortnight. Your staff have a Post-it note.

Every time someone tries to make a system more secure, the system gets less secure.

Tom and Corissa roam from hospital proximity sensors to vibe-coded spreadsheets, and find the same story playing out everywhere: different incentives, predictable workarounds, and a cycle that will keep going long after the technology changes.

• Why the most dangerous thing about a security measure might be how annoying it is
• Geoff the tinkerer, his idiosyncratic Excel spreadsheet, and what might happen when he gets access to an AI coding tool
• "A pandemonium of stochastic parrots" — what frontier engineering teams are actually learning about agent swarms (and it's not what the headlines say)
• The DevOps precedent: what happened to the person whose whole career was named-server maintenance, and how that rhymes with now
• Why your entire product sprint team might look, from the CEO's perspective, like a very slow LLM
• The one thing we can reliably predict about how AI will change organisations — even if everything else is uncertain

For anyone trying to figure out where to place their bets — on career, on technology, on their team — when the only honest answer is that nobody knows.

Links & references

• Simon Wardley (and his models for how technology and practice co-evolve)
• Clayton Christensen (Innovator's Dilemma, disruption theory)
• Episode 134: Geoff's shadow spreadsheet sprawl https://shows.acast.com/tentacles/episodes/696fea603738e9e7d196e2f5
• Episode 127: The unbundling and bundling of jobs https://shows.acast.com/tentacles/episodes/6920570d4105c9a02176f2bc

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Everyone’s got an opinion on vibe coding. Half the internet says it will save you £150,000 a year and you will never need a developer again. The other half says it is a dumpster fire of security holes and spaghetti code. Both camps are loud. Both camps are partially right. And lots of us watching the bunfight are just confused.

In this one, Tom and Corissa try to make sense of it — not by picking a side, but by honing some questions. Their lens is: bounded applicability. Some tools are good for some things. Nothing is good for everything. The hard part is knowing which is which.

Including-but-not-limited-to:

• Tom’s first proper foray into Claude Code, a surprisingly useful Python script it produced in 15 minutes
• A practical rubric: the questions to ask before you let an AI mess with your stuff
• The developer who reviewed and approved every chunk of code and then came back a week later to find chaos
• The architect’s clever marketing stunt that was already broken by the time anyone tried it
• Why the surface sheen of coherence stops you thinking critically
• Dave Snowden’s quietly devastating observation about what we’re actually doing when we accept AI outputs
• Vibe-coded accounting software ... a brief thought experiment

This one's for anyone trying to navigate the hype — in any direction — without losing their critical faculties in the process.

Links & references

• Theodore Sturgeon — science fiction writer; originator of Sturgeon’s Law (90% of everything is crap)
• Children of Time by Adrian Tchaikovsky
• Dave Snowden, cited via Corissa’s recollection of a LinkedIn post about AI
• Episode 039: Bounded Applicability — the concept underpinning this episode’s diagnostic framework

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You're doing everything right. The team is working hard, the process looks sensible, the effort is real. And yet — somehow — it's still not working. And nobody quite wants to say why.

In this one, we use our own dance teaching as a live case study in kill, pivot, commit decisions: two years of tweaks, probes, and exhausted options before one unexpected forcing function finally made the decision for them.

• Why the real problem is often visible — but no one can look at it straight on
• The difference between a panicked pivot and one that feels like settling (the good kind)
• How "problems grow to the size they need to" before you can act — and what that costs in the meantime
• The invisible organisational boundaries that make the logical option impossible
• Why loyalty to early customers makes the necessary pivot harder than it should be
• The Transactional Analysis trap that turns your friends into an audience for a problem you don't actually want solved
• Fat Duck or McDonald's — and why the middle is the worst place to be

For anyone who's been doing the sensible thing for long enough to suspect the sensible thing isn't working.

Links & References

• Luca Dellanna's 100 Truths You Will Learn Too Late https://luca-dellanna.com/books
• Eric Berne's Games People Play, including "Why Don't You — Yes But" https://en.wikipedia.org/wiki/Games_People_Play_(book)
• Adam Mastroianni's Experimental History https://www.experimental-history.com/p/two-stupid-facts-that-rule-the-world

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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 common
• Why "just be more playful" is almost as useless as "just be more strategic" — and practical stuff you can do instead
• Uncertainty bubbles: how to artificially impose the right kind of pressure so that different things can emerge
• Front-loading the nightmare — and why Pitch Provocations deliberately generates high-signal feedback when everything is still wrong
• The hidden cost of over-investing before you've tested: stress that balloons, sunk costs, and projects that polish the wrong thing
• Why improv, Lindy Hop, and safe-to-fail experiments are the same muscle — and how to build it somewhere low-stakes first
• Strategy 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: [email protected]

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/698de53934f221647e8927ea
• Donald Cox – friend of Tentacles who shared the point that there's only a little strategy at any one time at the company level
• Viktor Frankl — Man's Search for Meaning
• Dave Snowden — stress, innovation, and exaptation
• Memento Mori
• Internal locus of control
• Pitch Provocations method (episodes 007–009 for intro)
• Uncertainty bubbles — Crown & Reach concept, find out more when we share at https://reach.crownandreach.com
• Multiverse Mapping — https://multiversemapping.com
• Angie Lina — improv teacher and strategy/sense-making practitioner, former LSE Lindy Hop student

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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 out
• Signal > Stories > Options: how telling yourself different stories unlocks different actions
• Context, Proposition, Triggers (CPT) - a back-briefing technique that helps you test assumptions and get clearer direction
• Why diligent people can get penalised for doing exactly what the organisation says it wants
• When 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: [email protected]

References and linky goodness:

• John Grant (labour market researcher, Cynefin Slack community member)
• Dave Snowden
• Stealing the Corner Office by Brendan Reid
• Signal > Stories > Options framework (Crown & Reach) https://triggerstrategy.substack.com/p/signals-stories-options
• Context, Proposition, Triggers (CPT) https://reach.crownandreach.com/posts/mini-pitches
• Multiverse Mapping: https://multiversemapping.com
• Pitch Provocations method (referenced, episodes 007-009): https://shows.acast.com/triggerstrategy
• Cynefin Co's upcoming training (covers all seven frameworks including Estuarine Mapping) https://thecynefin.co/product/masterclass-7-frameworks-uk-2026-2/

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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 return
• The CEO confession that reveals what most executives are actually thinking during transformation
• What happens when you're getting your product (show, strategy, service, ...) ready in the way that normally works ... but the context keeps changing
• Substrate, 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 planning
• Why 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

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"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 management
• The 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 hands
• How expert oil rig workers can land helicopters in storms through tacit knowledge no checklist could capture
• The difference between a checklist, a flow chart, and knowing when neither will save you
• How 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 concept
• Vaughn Tan – "boring tiny tools" concept https://vaughntan.org/bttparadigm
• Ignaz Semmelweis – 19th-century physician who pioneered handwashing
• Atul Gawande – Author of The Checklist Manifesto
• Dave Snowden – Cynefin framework / oil rig helicopter story
• Gary Klein – Expert intuition and pattern recognition
• Procrustes – Greek mythology (innkeeper with the "one-size-fits-all" bed)
• Chick sexing – Example of tacit knowledge that can't be articulated
• Social protocols – Norms like cheek-kissing customs across cultures
• Simple Mail Transfer Protocol (SMTP) / Hypertext Transfer Protocol (HTTP) – Technical protocol examples

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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 emergence
• Why we'll never do much cold outreach, even though it works for others, and what we're doing instead
• The 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 Uncertainty
• Granularity, disintermediation and iteration (our hidden facilitation principles)
• Innovation Tactics (Tom's Pip Decks card deck - 50+ methods) https://collabs.shop/yxzsjg
• Decking metaphor episode (our previous year-in-review)

What's your theme for the year? Did anything in this episode trigger a thought for you? [email protected]

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