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Lane Shackleton (CPO of Coda)01 October 2023

What sets great teams apart

9Frameworks
15Insights

Episode overview

Lane Shackleton argues that a product leader’s core job is turning ambiguity into clarity, supported by principles such as systems over goals, cathedrals over bricks, and learning through making. He explains team rituals including FlashTags, Catalyst, $100 Voting, tag-ups, Dory, and two-way write-ups, showing how they improve feedback calibration, decision throughput, and inclusive discussion. He also traces his path from mountain guiding and customer support to product leadership, emphasizing preparation, customer proximity, active listening, and deliberately seeking career-stretching experiences.

Key ideas

  • A product person’s core job is to spot ambiguity and turn it into clarity.
  • Reliable systems—such as recurring customer conversations—produce better results than isolated goals with good intentions.
  • Teams perform better when people understand the larger “cathedral” they are building, presented through multiple concrete perspectives.
  • When debate stalls, teams should learn by making: test extremes, run an experiment, build a prototype, or write a concrete proposal.
  • FlashTags calibrate feedback as FYI, suggestion, recommendation, or plea so teams know what deserves the most attention.
  • Catalyst improves review throughput by dynamically assembling the right attendees and running non-overlapping topics in parallel.
  • Two-way write-ups incorporate reading signals, upvoted questions, and explicit sentiment into the document rather than relegating discussion to comments.
  • Strategy should be separated from OKR setting, and planning should consume no more than roughly 10% of the execution period.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 21

  • Lane ShackletonMentionsI had with Lane Shackleton from Kota and you shared this framework called flash tags

    today my guest is Lane Shackleton

  • Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter

    welcome to Lenny's podcast where interview worldclass product leaders and growth experts

  • Ernest ShackletonMentionsExplorer whose expedition is recounted in Endurance.

    that's as close as I can I can come to the the greatness of Ernest Shackleton

  • Bret VictorCoinedthis guy named Brett Victor who's kind of like a prot prot typer thinker

    I was pretty inspired by a talk that is by this guy named Brett Victor

  • Jeremy BrittainMentionsone of our first designers this guy Jeremy Brittain showed this talk to the company

    one of our first designers this guy Jeremy Brittain showed this talk to the company

  • Jerry SeinfeldMentionsone of the stories that I tell is basically the story of Jerry Seinfeld

    one of the stories that I tell is basically the story of Jerry Seinfeld

  • Rick RubinMentionsJack Clark is our you know head of policy and he got connected to Rick Rubin

    I believe it's from the Rick Rubin book

  • Matthew DicksCoinedhe helps people create their eulogy ahead of time before somebody passes away

    we ended up bringing him into Kota and he gave a great talk so yeah big big plug for Matthew Di

  • Seth GodinCoinedSeth is an absolute Legend he's published 21 books including 18 International bestsellers

    I think I picked this up originally from Seth Goden the author

  • Ryan HolidayCoinedmentioned

    it's a great book by Ryan holiday

  • Tony FadellCoinedHe co-created some of the most innovative and beautiful and popular products in history. The iPod, the iPhone, the Nest thermostat.

    Tony Fidel has a great talk on this

  • Shishir MehrotraMentionsshashir marocha is the co-founder and ceo of koda before starting koda shashir led the youtube product engineering and design teams

    shashir is writing a book called rituals of great teams

  • Dharmesh ShahCoinedone of the attendees there is darmesh founder of hubspot and very thoughtful person

    dares Shaw has this this Ritual from HubSpot called flash tags

  • Phil FarhiMentionsthis guy named Phil fary who's amazing product leader and was my boss at the time

    this guy named Phil fary who's amazing product leader and was my boss at the time

  • Sheryl SandbergMentionsI was at a fireside chat with Cheryl Sandberg once at Airbnb

    started in Cheryl samberg's organization

  • Chip ConleyMentionshe created the ri Hotel chain and just like his steepen hospitality

    at Airbnb we hired this guy chip Connelly who was a hotelier

  • Tim FerrissMentionsCited for his fear-setting framework and as an influence on Paul Millerd's five-episode podcast experiment.

    one of them was uh Tim Ferris day

  • Jeff BezosMentionsthe Jeff Bezos thing that like the success of today was set in motion three years ago

    Jeff Bezos sent this very famous memo which basically said no more PowerPoint at Amazon

  • Jim CollinsCoinedmentioned

    it's a little manuscript book Jim Collins wrote it

  • Timothy GallweyCoinedmentioned

    the inner game of tennis by Timothy gway

  • Sam HarrisCoinedSam Harris talks about this a lot that it feels like once you get close then it could just accelerate so quickly

    waking up is a book by Sam Harris on mindfulness that I really like

Resources · 35

  • GoogleMentionscompany · Google

    before that he was group product manager at YouTube a product specialist at Google

  • EppoMentionssoftware · Eppo

    this episode is brought to you by EPO EPO is a Next Generation AB testing plat platform

  • AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk

    when I was at Airbnb one of the things that I loved most about working there was our experimentation platform

  • VantaMentionssoftware · Christina Cacioppo

    this episode is brought to you by vanta helping you streamline your security compliance to accelerate your growth

  • EnduranceRecommendsbook · Alfred Lansing

    in high school we read endurance uh which is a great book if you haven't read it

  • Inventing on PrincipleCoinedcourse · Bret Victor

    he has this talk called inventing on principle

  • ComedianRecommendsdocumentary · Christian Charles

    if you haven't seen the documentary to me median it's amazing it's definitely worth watching

  • CodaUsessoftware · Coda

    in the early days of Kota we actually did something similar

  • The Score Takes Care of ItselfMentionsbook · Bill Walsh

    also makes me think about this book uh the score takes care of itself

  • AlphaGoMentionssoftware · DeepMind

    alpha zero or Alpha go the first AI thing that beat humans at go

  • SubstackUseswebsite · Substack Inc.

    lane. substack

  • StoryworthyRecommendsbook · Matthew Dicks

    there's a book called story worthy that I really like

  • The Moth StorySLAMRecommendsevent · The Moth

    you go to the moth story slam you're to see some like really good stories

  • The Obstacle Is the WayRecommendsbook · Ryan Holiday

    have you read the book The obstacle is the way

  • HubSpotCoinedcompany · HubSpot

    this this Ritual from HubSpot called flash tags

  • FlashTagsUsesother · Dharmesh Shah

    so we have ended up using that

  • EzraUsescompany

    I actually used Ezra earlier this year unrelated to this podcast completely on my own dime

  • CatalystCoinedother · Coda

    we built Catalyst to really solve those two problems

  • $100 VotingUsesother

    another one of my favorites there is $100 voting uh we use that a lot in the context of planning

  • Pixar BraintrustMentionsother · Pixar

    it's kind of modeled off after Pixar's Brain Trust

  • AdWordsUsessoftware · Google

    after working on ad approvals at that time I moved to chat support it was basically like when adwards was launching chat support

  • PowerPointMentionssoftware · Microsoft

    the first phase was uh 1980s we had PowerPoint

  • Google DocsMentionssoftware · Google

    Google bought this company called rightly that became Google Docs

  • Working BackwardsRecommendsbook · Colin Bryar and Bill Carr

    you can read all about this in the book working backwards really good really good book

  • DoryUsesother · Coda

    that's what we call Dory

  • Turning the FlywheelRecommendsbook · Jim Collins

    one that comes to mind is turning the flywheel

  • Good Strategy/Bad StrategyRecommendsbook · Richard Rumelt

    good strategy bad strategy love that book very simple framework that I've reused a bunch

  • Waking UpRecommendssoftware · Sam Harris

    waking up is a book by Sam Harris on mindfulness that I really like

  • The Inner Game of TennisRecommendsbook · W. Timothy Gallwey

    an old one that I really like is the inner game of tennis

  • The Last DanceRecommendsdocumentary · ESPN Films and Netflix

    I really enjoyed the last dance I like love any sports documentary

  • Stephen Curry: UnderratedRecommendsdocumentary

    have you seen underrated Steph Curry's new documentary

  • Arrested DevelopmentRecommendstv show · Mitchell Hurwitz

    I've been rewatching Arrested Development that's that's also just a a Timeless classic

  • ChatGPTRecommendssoftware · OpenAI

    obviously in the tech world like Chad GPT

  • SwingVisionRecommendssoftware

    there's a product called swing Vision that's really good

  • Waking UpRecommendssoftware · Sam Harris

    there's a corresponding meditation app uh to the book waking up that I really like

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster1:04:30

Customers Don't Care About Your Product, They Care About Their Problem

From AdWords support, Lane learned that customers didn't care about ad groups or formats; the small business owner just wanted more phone calls or people in the store. The product has to get out of the way and drive impact. Lenny echoes it with Airbnb hosts, who see their home, not the website's features, as the product. Assuming people don't care forces sharper communication.

  • AdWords customers didn't care about the product, they wanted more calls or foot traffic
  • The product has to get out of the way and just drive impact for the customer
  • Airbnb hosts thought their home was the product, not the website's features
  • Assuming people don't care forces you to communicate more concisely

it's just a great lesson in when people don't actually care about your product

Lane Shackleton · 1:04:30

you should assume that they don't care when you start with that assumption you really force yourself to be a little bit sharper

Lane Shackleton · 1:10:30
#customer#communication#product-management#positioning

Hot Take· 2

Hot Take12:30

Why Coda Uses Five 'Role Stages' Instead of 15 Levels

Coda deliberately delayed introducing career ladders because titling flips incentives from company-focused to individual-focused. When they did, they built only five role stages (Apprentice to Principal) instead of the 10-15 levels most large companies use, kept levels invisible across the company, and put compensation in the hands of a centralized committee rather than managers.

  • They put off ladders on the advice that levels flip incentives toward the individual
  • Only five role stages, Apprentice through Principal, with a deliberately very high bar at the top
  • Role stages are not visible across the company and titles aren't emphasized
  • A centralized compensation committee, not the manager, decides pay

as soon as you introduce this then the incentives sort of like flip from being company focused to being individual focused

Lane Shackleton · 13:00

I think most other companies especially large companies has have 10 to 15 levels I think we've made a really conscious choice to have only…

Lane Shackleton · 15:00
#org-design#career-ladders#compensation#management
Hot Take1:01:00

Shipping Changes Is Almost Never as Bad as You Fear

Riffing on Twitter agonizing for years over the edit button before eventually shipping changes rapidly with no disaster, Lane argues teams are too delicate about changes. In his experience it's almost never as bad as you think, so the real question isn't whether a change will break things but how much better it could make them.

  • Twitter spent years overthinking small changes like the edit button, then shipped fast and fine
  • Teams don't need to be so delicate about product changes
  • The outcome is almost never as bad as you fear
  • The better question is how much better a change could be

it's it's almost never as bad as you think it's going to be so yeah it's just a question of how how much better it…

Lane Shackleton · 1:01:30
#shipping#risk#decision-making

Story· 4

Story05:30

The Near-Death Fall That Ended Lane's Mountain-Guiding Career

Before product, Lane Shackleton guided climbers in Alaska. On a dream trip up a 15,000-foot peak, a client he was roped to fell near the summit and Lane had to self-arrest the fall. Spending six hours walking down the mountain thinking he could die tied to a near-stranger convinced him to leave guiding.

  • Guides rope themselves to clients on glaciers so they can arrest a fall into a crevasse
  • A client fell near the top of a descent; Lane was able to self-arrest and stop the fall
  • The experience of being roped to someone he barely knew, with his life on the line, ended his guiding career

I really don't want to die you know rope to someone that I barely know and like don't trust or love so that was that…

Lane Shackleton · 07:00
#career#risk#mountaineering#origin-story
Story22:30

AlphaGo's Move 37 and the Power of Beginner's Mind

Lenny recounts AlphaGo's famous move 37, so alien that its human opponent walked out of the room. The lesson: the AI trained itself from first principles rather than on what humans had already learned, and produced something no one had comprehended. Lane connects this to Coda's walkthrough ritual, where you approach a topic as if you know nothing about it.

  • AlphaGo's move 37 was so unexpected the human opponent left the room mid-game
  • The AI trained itself from first principles rather than on human-learned patterns
  • Beginner's mind, not being anchored to what's already been done, unlocks new ideas

there's a move it made move 37 in a game that was just like like the person the AI was playing walked out of the…

Lenny Rachitsky · 23:00

it was training not on what we've learned but it trained itself and figured things out from first principles

Lenny Rachitsky · 23:30
#first-principles#creativity#ai#beginners-mind
Story57:00

How YouTube's Skippable Ads Got Unstuck: Test the Extremes

As a brand-new PM at YouTube, Lane was handed the project nobody wanted: skippable ads, which advertisers, the sales team, and almost everyone else opposed. Stuck debating an unproven thesis, his boss Phil Farhi told him to stop debating and just test the extremes, tiny skip button versus a giant one covering the whole player. Within weeks the data gave them conviction.

  • Skippable ads was the project nobody wanted, opposed by advertisers and sales
  • Rather than debate for months, run experiments testing the upper and lower bounds
  • One experiment used a tiny skip button, another a giant one covering the whole player
  • The broader lesson: stop talking and go make something, a prototype, doc, mock, or experiment

just test the extremes start the experiment tomorrow like then we'll what we'll figure it out

Lane Shackleton · 59:30

stop talking about it and like go make something go go like run an experiment go make a prototype

Lane Shackleton · 1:00:30
#experimentation#decision-making#youtube#product-management
Story1:11:00

The Day a Tim Ferriss Newsletter Broke Coda's Analytics

A Coda team member quietly built one of Tim Ferriss's rituals into a doc and got it in front of him. One morning traffic and signups spiked so hard Lane was convinced it was spam; amid the chaos a fire alarm sent the team outside to their laptops in a war room. It turned out Ferriss had featured them in his newsletter, and 'Tim Ferriss Day' taught Coda the power of content distribution.

  • A team member implemented one of Tim Ferriss's rituals and got an intro to him
  • Traffic and signups spiked so hard Lane assumed it was spam or a data problem
  • A fire alarm forced the war-room investigation outside onto laptops
  • Ferriss had featured Coda in his newsletter, teaching the 'second-time founder builds distribution' lesson

firsttime founder build a great product second time founder build great distribution

Lane Shackleton · 1:12:30
#distribution#growth#content#story

Tool· 2

Tool29:00

Story Worthy: A Great Story Is Five Seconds of Transformation

Lane recommends Matthew Dicks's book Story Worthy as the most practical guide to telling stories. Its core insight is that the nugget of a great story is a five-second moment of transformation; orient everything else around that moment and you'll usually tell a good story. Lane was so taken with it that Coda brought Dicks in to give a talk.

  • Book recommendation: Story Worthy by Matthew Dicks
  • The core of any great story is a roughly five-second moment of transformation
  • Orient everything else around that moment of change to tell a good story
  • Coda brought the author in to give a talk after Lane read it

the Nugget of a great story is like five seconds of transformation

Lane Shackleton · 29:00
#storytelling#books#communication
Tool1:21:30

Lane Shackleton's Most-Recommended Books

In the lightning round, Lane lists the books he recommends most: Turning the Flywheel by Jim Collins (a short, fast read on how flywheels work), Story Worthy, Good Strategy Bad Strategy (a simple framework he's reused often, even outside tech), Waking Up by Sam Harris on mindfulness, and the classic The Inner Game of Tennis by Timothy Gallwey.

  • Turning the Flywheel by Jim Collins, a succinct manuscript on how flywheels work
  • Good Strategy Bad Strategy, a simple framework he's reused a lot, including outside tech
  • Waking Up by Sam Harris on mindfulness
  • The Inner Game of Tennis by Timothy Gallwey, an older classic

one that comes to mind is turning the flywheel it's a little manuscript book Jim Collins wrote it

Lane Shackleton · 1:22:00
#books#strategy#recommendations

Takeaway· 6

Takeaway07:30

What Mountain Guiding Taught Lane About Building Software

Lane draws direct parallels between expedition guiding and product work: months of preparation for a few days of execution, redundant checklists across every system, and staying calm under pressure. When a client broke both feet on a climb, the senior guide's calm sequence of assess, prioritize, act became a template Lane still uses in software.

  • Climbing means months of preparation for only a few days of actual climbing
  • Checklists run a dozen-plus times ensure redundancy across all systems
  • In a crisis the model is: stay calm, assess the situation, prioritize, take action

stay calm assess the situation prioritize take action

Lane Shackleton · 08:30
#leadership#preparation#crisis-management
Takeaway21:30

The Rick Rubin Listening Lesson Every PM Should Steal

Lane admires Rick Rubin's approach to listening: absorb every fragment of what someone is saying, including body language, while turning off the internal voice that's crafting your response or finding holes in their argument. It's hard because the default mode is always jumping to the next step of the conversation, but internalizing what the person actually means is powerful.

  • Absorb every fragment of what the person is saying, including body language
  • Turn off the side of your brain crafting your response or planning a rebuttal
  • The default mode is always the next step of the conversation, which makes real listening hard

you want to listen and absorb sort of every fragment of what that person is saying including you know their body language and everything else…

Lane Shackleton · 22:00
#listening#communication#product-management
Takeaway31:30

A Sharper Way to Know If You're Actually Growing

Picked up from author Seth Godin, Lane uses uncomfortable, out-of-your-depth moments as the real signal of career growth. Instead of the vague 'do you feel like you're growing?', he asks how many moments in the last six months, year, or two years made you feel underqualified. If it's been a long time since you were stretched, that's worth digging into.

  • The moments where you feel underqualified are the ones you should seek out
  • They stretch you and give you a new foundation
  • Replace the vague 'are you growing?' with 'how many stretch moments have you had recently?'
  • A long gap since feeling stretched is a signal something needs to change

a much sharper way is like hey how many like oh [ __ ] moments have you had in the last like six months year two years…

Lane Shackleton · 32:30
#career#growth#self-assessment
Takeaway1:03:30

Get Customer-Facing From the Very Beginning of Your Career

Lane started in tech reviewing AdWords ads, then did chat and phone support. A mentor's advice, that you'll serve a customer your whole career even as a CEO, so get good at any customer scenario early, turned out to be some of the best he ever received. He's recycled it for people earlier in their careers ever since.

  • You end up serving a customer your entire career, even as CEO
  • Get good at handling any customer scenario as early as possible
  • A customer-facing role makes you the expert on the customer, which is undervalued in tech
  • That customer knowledge can be leveraged into a PM role

you have to get customer facing from the very beginning because you're going to end up serving a customer your whole career

Lane Shackleton · 1:04:00
#career#customer#mentorship#product-management
Takeaway1:19:30

OKRs Aren't Strategy, and the 10% Planning Rule

Lane shares two planning insights Coda lives by. First, OKRs are not strategy; it's critical to keep strategy discussions distinct from OKR, metric, and goal setting. Second, the hard-won 10% planning rule: never spend more than 10% of an execution period planning for it, because over-planning fogs teams down and you rarely know what's ahead until you've launched or learned.

  • OKRs are not actually strategy; separate strategy discussions from goal and metric setting
  • Ask whether you have a distinct strategy ritual apart from OKR setting
  • The 10% planning rule: plan for no more than 10% of the execution period
  • Over-planning is a common, hard-to-avoid mistake since you don't know what's ahead until you launch

okrs are not actually strategy

Lane Shackleton · 1:20:00

10% planning rule which is essentially you know just ensure that you're not for a given time period planning for more than 10% of that…

Lane Shackleton · 1:20:30
#strategy#planning#okrs#process
Takeaway1:27:00

The Safest Climber Is the One Who Knows When to Come Down

Asked for climbing advice, Lane offers a saying that doubles as a life and career lesson: the safest climber is the one who knows when to come down. Many times you have to put your ego in check and come off a mountain because it isn't as safe as you thought. He adds that pursuing climbing is usually not a one-way door.

  • The safest climber is the one who knows when to turn back
  • You often have to put your ego in check and come off a mountain
  • Climbing and outdoor pursuits are usually not a one-way door; you can come back to them

the safest climber is the one who knows when to come down

Lane Shackleton · 1:27:30
#climbing#decision-making#ego#life-lessons