Humor and Leadership in High-Stakes Conversations

David DeSanto is the chief product officer of GitLab, which is the largest remote-only company in the world. They share many of their team meetings on YouTube, and they’ve grown from being an open-source code management product competing with GitHub to a multi-product platform that covers security, compliance, continuous integration, project management, and deployment tools, many of which are infused with AI magic. In our conversation, we discuss:

• How GitLab operationalizes transparency

• The philosophy behind recording and sharing team meetings on YouTube

• Their extensive public employee handbook

• GitLab’s core value of having “short toes”

• Challenges and advice for doing remote work well

• Strategies for ensuring effective communication in a remote work environment

• GitLab’s breadth-over-depth strategy

• The company’s unique approach to AI

• The value of using humor in high-stakes conversations

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Find the transcript at: https://www.lennysnewsletter.com/p/the-gitlab-way

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Where to find David DeSanto:

• X: https://twitter.com/david_desanto

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

• Threads: https://www.threads.net/@david.the.beard

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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) David’s background

(04:20) Maintaining an epic beard

(05:29) Why GitLab publicly shares team meetings

(09:49) The GitLab Handbook

(11:30) GitLab’s issue tracker

(14:29) How to successfully build a culture of transparency

(18:11) Benefits of operating with transparency

(19:55) The value of building in public

(21:53) How GitLab implements their core value of kindness

(25:16) What it means to have “short toes”

(27:41) Other core values

(32:16) Common reasons for not fitting in at GitLab

(34:42) Advice for remote teams

(42:04) Advice for getting into product

(43:52) Advice for PMs who are struggling in a remote world

(48:25) Specific tools that help with remote work

(53:13) Time zones and remote work

(57:18) Breadth-over-depth strategy

(01:04:14) AI at GitLab

(01:13:11) GitLab’s products and solutions

(01:14:54) Lightning round

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Referenced:

• GitLab: https://about.gitlab.com/

• UX Showcase—David DeSanto introduction to UX team and AMA: https://www.youtube.com/watch?v=fEdsmnVKNj4

• The GitLab Handbook: https://handbook.gitlab.com/

• Sid Sijbrandij on LinkedIn: https://www.linkedin.com/in/sijbrandij/

• Y Combinator: https://www.ycombinator.com/

• GitLab issues: https://docs.gitlab.com/ee/user/project/issues/

• Salesforce: https://www.salesforce.com/

• GitLab values: https://handbook.gitlab.com/handbook/values

• GitLab organizational structure: https://handbook.gitlab.com/handbook/company/structure

• GitLab direction: https://about.gitlab.com/direction/

• Dogfooding: A simple practice to help you build better products: https://medium.com/agileinsider/dogfooding-a-simple-practice-to-help-you-build-better-products-b5954af4d5f7

• The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-adding-a-plg

• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

• HubSpot: https://www.hubspot.com/

• Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986

• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennyspodcast.com/geoffrey-moore-on-finding-your-beachhead-crossing-the-chasm-and-dominating-a-market/

• Open-core model: https://en.wikipedia.org/wiki/Open-core_model

• GitLab Duo: https://about.gitlab.com/gitlab-duo/

• GitLab Docs: https://docs.gitlab.com/

• Anthropic: https://www.anthropic.com/

• GitLab Acquires UnReview to Expand Its DevOps Platform with Machine Learning Capabilities: https://about.gitlab.com/press/releases/2021-06-02-gitlab-acquires-unreview-machine-learning-capabilities/

• Essentialism: The Disciplined Pursuit of Less: https://www.amazon.com/Essentialism-Disciplined-Pursuit-Greg-McKeown/dp/0804137382

• The Mission Critical Core/Context Model for Product Managers: https://secretpmhandbook.com/the-mission-critical-corecontext-model-for-product-managers/

• The Devil’s Hour on AppleTV+: https://tv.apple.com/us/show/the-devils-hour/umc.cmc.3zw4tyzd4lvor5mwhujms63x3

• Glass Onion: A Knives Out Mystery on Netflix: https://www.netflix.com/title/81458416

• Taylor Swift’s The Eras Tour on Prime Video: https://www.amazon.com/TAYLOR-SWIFT-ERAS-EXTENDED-VERSION/dp/B0CP99SN2B

• The STAR method: https://capd.mit.edu/resources/the-star-method-for-behavioral-interviews/

• Artifact News: https://artifact.news/

• Superhuman: https://superhuman.com/

• Arc browser: https://arc.net/

• An inside look at how The Browser Company builds product: https://www.lennysnewsletter.com/p/competing-with-giants-an-inside-look

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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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