Separating Strategy from Execution: Insights on Planning

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Lane Shackleton is CPO of Coda, where he’s been leading the product and design team for over eight years. Lane started his career as an Alaskan climbing guide and then as a manual reviewer of AdWords ads before becoming a product specialist at Google and later a Group PM at YouTube. He also writes a weekly newsletter with insights and rituals for PMs, product teams, and startups. In today’s conversation, we discuss:• Principles that set great PMs apart• Rituals of great product teams• The fine line between OKRs and strategy, and why it matters• “Two-way write-up”• The story of how skippable YouTube ads were born and lessons learned• How to gauge personal career growth• “Tim Ferriss Day” and its impact on Coda’s history• How Lane bootstrapped his way to CPO from the bottom of the tech ladder

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Find the transcript and references at: https://www.lennyspodcast.com/what-sets-great-teams-apart-lane-shackleton-cpo-of-coda/ 

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Where to find Lane Shackleton:

• X: https://twitter.com/lshackleton

• LinkedIn: https://www.linkedin.com/in/laneshackleton

• Substack: https://lane.substack.com/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Lane’s background

(04:03) Working as a guide in Alaska

(07:32) Parallels between guiding and building software

(09:12) Why Lane started studying and writing about product teams

(12:49) How Lane came up with the career ladder and guiding principles

(14:10) The five levels Coda’s career ladder

(16:30) Principles of great product managers

(21:06) The beginner’s-mind ritual at Coda

(24:05) Two rituals: “cathedrals not bricks” and “proactive not reactive”

(27:46) How to develop your own guiding principles

(31:17) Learning from your “oh s**t” moments

(36:03) Rituals from great product teams: HubSpot’s FlashTags

(42:15) Rituals from great product teams: Coda’s Catalyst

(47:01) Implementing rituals from other companies

(49:48) How to navigate changing vs. sticking with current rituals

(53:02) “Tag up” and why one-on-one meetings are harmful 

(55:27) Lane’s handbook on strategy and rituals

(57:10) How skippable ads came about on YouTube   

(1:01:46) Lane’s path to CPO

(1:07:02) Advice for aspiring PMs

(1:10:53) Tim Ferriss Day at Coda

(1:13:24) Using two-way write-ups 

(1:19:30) The fine line between OKRs and strategy, and why it matters

(1:21:41) Lightning round

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Referenced:

• Endurance: https://www.amazon.com/Endurance-Shackletons-Incredible-Alfred-Lansing/dp/0465062881

• Bret Victor’s talk “Inventing on Principle”: https://www.youtube.com/watch?v=EGqwXt90ZqA

• Jeremy Britton on LinkedIn: https://www.linkedin.com/in/jeremybritton/

• Comedian on Netflix: https://www.netflix.com/title/60024976

• The Score Takes Care of Itself: My Philosophy of Leadership: https://www.amazon.com/Score-Takes-Care-Itself-Philosophy/dp/1591843472

• The Creative Act: A Way of Being: https://www.amazon.com/Creative-Act-Way-Being/dp/0593652886

• AlphaZero: https://en.wikipedia.org/wiki/AlphaZero

• Antoine de Saint-Exupéry: https://en.wikipedia.org/wiki/Antoine_de_Saint-Exup%C3%A9ry

• Storyworthy: Engage, Teach, Persuade, and Change Your Life through the Power of Storytelling: https://www.amazon.com/Storyworthy-Engage-Persuade-through-Storytelling/dp/1608685489

• The Moth: https://themoth.org/events

• Seth Godin’s website: https://www.sethgodin.com/

• The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph: https://www.amazon.com/Obstacle-Way-Timeless-Turning-Triumph/dp/1591846358

• Tony Fadell’s TED talk: https://www.youtube.com/watch?v=9uOMectkCCs

• FlashTags: A Simple Hack for Conveying Context Without Confusion: https://www.onstartups.com/flashtags-a-simple-hack-for-conveying-context-without-confusion

• How Coda builds product: https://www.lennysnewsletter.com/p/how-coda-builds-product

• 100-dollar voting ritual: https://coda.io/@lshackleton/100-dollar-voting-exercise

• Pixar’s Brain Trust: https://pixar.fandom.com/wiki/Brain_Trust

• Lane’s product handbook: coda.io/producthandbook

• The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/

• Principle #4: Learn by making, not talking: https://lane.substack.com/p/principle-4-learn-by-making-not-talking

• Phil Farhi on LinkedIn: https://www.linkedin.com/in/philfarhi/

• How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit): https://www.lennyspodcast.com/how-to-ask-the-right-questions-project-confidence-and-win-over-skeptics-paige-costello-asana-intercom-intuit/

• Chip Conley’s website: https://chipconley.com/

• Jeff Bezos Banned PowerPoint in Meetings. His Replacement Is Brilliant: https://www.inc.com/carmine-gallo/jeff-bezos-bans-powerpoint-in-meetings-his-replacement-is-brilliant.html

• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595

• Dory and Pulse: https://coda.io/@codatemplates/dory-and-pulse

• Turning the Flywheel: A Monograph to Accompany Good to Great: https://www.amazon.com/Turning-Flywheel-Monograph-Accompany-Great/dp/0062933795/

• Waking Up: A Guide to Spirituality Without Religion: https://www.amazon.com/Waking-Up-Spirituality-Without-Religion/dp/1451636024

• The Inner Game of Tennis: The Classic Guide to the Mental Side of Peak Performance: https://www.amazon.com/Inner-Game-Tennis-Classic-Performance/dp/0679778314

• Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239

• The Last Dance on Netflix: https://www.netflix.com/title/80203144

• Full Swing on Netflix: https://www.netflix.com/title/81483353

• Stephen Curry: Underrated on AppleTV+: https://tv.apple.com/us/movie/stephen-curry-underrated/umc.cmc.23v0wxaiwz60bjy1w4vg7npun

• Arrested Development on Netflix: https://www.netflix.com/title/70140358

• Shishir’s interview question clip on TikTok: https://www.tiktok.com/@lennyrachitsky/video/7160779872296652078

• The Ultimate Reference Check Template: https://coda.io/@startup-hiring/reference-checks-template

• SwingVision: https://swing.tennis/

• Waking Up app: https://www.wakingup.com/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

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