Tom Kerwin

Tentacles - the podcast from Crown & Reach

Business EN ↓ 49 episodes

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.

Be sure to visit the podcast's website and support the creator: feeds.acast.com

Author

Tom Kerwin

Category

Business

Podcast website

feeds.acast.com

Latest episode

Sep 9, 2026

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Episodes

153: Tom's worst ever DJ set 09.09.2026

Tom's worst ever DJ set was one where he followed the "rules" most carefully. His best was the one where he stopped trying. And the difference relates to why many teams can do all the right exploratory work and still discover nothing useful. In this one we wander through DJing for swing dancers as a sort of live complexity practice, and then we crowbar lessons from rooms full of dancers into the w...

152: Dogfooding part 2 – wrongness-based enlightenment 02.09.2026

We ran our own method on ourselves, and it told us the word we'd built everything on was the wrong one. Four research calls in, the transcripts showed us that "positioning" probably isn't our positioning. That's exactly what our method is for, and exactly what nobody loves experiencing when it works. This one is part two of our series where we're dogfooding Pitch Provocations. Another walk, in the...

151: It's never lupus 01.09.2026

What can a fictional, addicted, borderline-unbearable doctor show us about stalled strategy projects? When we have a small baby, our TV diet needs to be relatively unchallenging, and we recently rediscovered House. And got talking about how their "differential diagnosis" — that whiteboard full of things the disease might be — is basically our Signals > Stories > Options stuff but with appare...

150: Dogfooding part 1 – or coordinating people to stare into the void 28.08.2026

We sell a method for getting teams unstuck on positioning. We've been stuck on our own positioning for years. At some point the two must collide. We've tried to run our method on ourselves before and it was hard. So this time we roped in a dear friend to run the process on us. Properly this time. We recorded the debrief while walking along with our two-month-old strapped to Tom's chest. This is al...

149: Someone else's thinking running through your own brain 19.08.2026

A quick request: we're running our own method on ourselves, and we want to speak with marketing leaders: marketing directors, VPs of marketing, CMOs, and anyone else who's trying to position or launch a new business line. No selling, just a listening tour! Participants usually find the conversation somewhere between enjoyable and cathartic. If you know someone, please take 2 mins and introduce us:...

148: Don't throw future you under the bus (many beefs with backcasting) 11.08.2026

A friend of the podcast got hired to run a facilitation: "vision on day one, backcasting on day two." He asked Tom for tips on backcasting workshops. Tom rolled up his sleeves and out fell a number of beefs. In this one we walk through why visions and step-by-step plans keep falling apart, and how to smuggle something that actually works into a workshop that's already been sold as backcasting. Inc...

147: The taco shop gambit 14.07.2026

What does a six-year-old cartoon dog have to do with a maverick fighter pilot's theory of strategy? In this one we feel our way through two theories of how humans create knowledge — David Deutsch's collaborative "Taking Children Seriously" and John Boyd's adversarial OODA loop — and discover that Bluey's dad needed both, and had neither. From bath-time burger shops to spitting toddlers, we try to...

146: Weak signals in AI – or it grew really tall and fell over 08.07.2026

More apps are shipping to the app stores, but the same number of apps are getting downloaded. In this one we're pushing a pram round Bournemouth with a one-month-old and making sense of the current AI moment — from the slop machine that online advertising has become to why the big frontier model bet may have misfired, and what a walking creature that just falls over can teach us about software dev...

145: What Xerox PARC actually got wrong 28.05.2026

Xerox PARC famously invented the mouse, the graphical user interface, and the printer — then watched Steve Jobs walk off with all of it. The usual lesson: silly management didn't recognise what they had. The actual lesson is more useful ... and more uncomfortable for innovator types. Sit in your beanbag so you can't storm off. In this one, we use Xerox PARC as a case study in what happens when an...

144: The domino rally delusion 24.05.2026

What do you do if Strategy Doesn't Exist? Tom and Corissa have built a strategy consultancy and they're here to tell you that strategy doesn't exist. At least, not in the way everyone sells it — and probably not in the way you've been trying to do it. This one was sparked by a recent episode from friends-of-Tentacles Kyle and Jen on Notes from the Swamp . We start with domino rallies and end up so...

143: The breadmaker trick 13.05.2026

Bread makers don't knead dough the way a human baker does. They get to the same result via a completely different route — and that turns out to be a pretty good map for what's actually happening with AI right now. We start with brioche, end up in a crisis of professional tacit knowledge, and find a surprisingly useful frame for thinking about what machines can and can't do — and what that costs us...

142: Sit with it 29.04.2026

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 immedia...

141: Indifference is the default 20.04.2026

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 friend...

140: A pandemonium of stochastic parrots 23.03.2026

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 incentive...

139: Sturgeon's Vibe Code 18.03.2026

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...

138: Kill, pivot, commit? … the swing dance switcheroo 05.03.2026

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 fo...

137: The six or seven problem when "being more strategic" 20.02.2026

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 co...

136: When they tell you to "be more strategic" (but not what that actually means) 12.02.2026

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 a...

135: The resistance to instability - and why Stewart Lee hasn't finished his show yet 06.02.2026

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 trad...

134: The Protocol Problem part 1 – Geoff's shadow spreadsheet sprawl 20.01.2026

"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...

133: Giant hats and fluffy aspirations - a year in review 16.01.2026

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 nea...

132: Skate where the poke is going 15.01.2026

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...

131: Safe-to-fail boops – a pragmatic critique of pseudo-scientific business experiments 13.01.2026

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 cr...

130: The Sinclair Effect and the Winkler Constraint 09.01.2026

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...

129: Who gets to decide what counts as an insight? 07.01.2026

Can "insights" be pre-packaged? Should they be? In this one, we wade into the murky distinction between polished agency deliverables and raw, messy data exposure. From a bank that knew what it wanted (and just needed to show due diligence) to clients who fundamentally changed direction after reading customer transcripts, we explore when different approaches can actually work. Along the way we talk...

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