The GitLab way: Kindness, transparency, and short toes | David DeSanto (CPO)

The GitLab way: Kindness, transparency, and short toes | David DeSanto (CPO)

David’s background (00:00:00)

  • GitLab is the largest remote-only company in the world.
  • They share many of their team meetings on YouTube.
  • GitLab has grown from being just a source code management business to a multi-product platform.
  • Many of GitLab's products are infused with AI magic.
  • GitLab is very transparent, sharing many things that most companies keep secret.
  • They believe that transparency builds trust and encourages collaboration.
  • GitLab shares things like team meeting videos, their handbook, and how they count PES.
  • Other companies have even forked GitLab's handbook.
  • "Short toes" means focusing on the work and not on yourself.
  • It helps to reduce negative headbutting, especially in an asynchronous culture like GitLab's.
  • When everyone is really annoyed with you, you're probably doing your job well.
  • Be intentional about creating a remote-first culture.
  • Use tools that are designed for remote work.
  • Encourage employees to take breaks and to set boundaries between work and personal life.
  • Build a strong sense of community among employees.
  • When launching new product lines, it's important to consider whether to go breadth over depth or depth over breadth.
  • GitLab has found that it's often better to go breadth over depth, as this allows them to reach a wider audience and get feedback from more users.

Maintaining an epic beard (00:04:20)

  • David DeSanto's beard requires regular maintenance.
  • He visits a trusted barber to maintain the shape of his beard.
  • He washes and conditions his beard regularly.
  • His Twitter handle is @davidthebeard.
  • GitLab's values are kindness, transparency, and efficiency.
  • Kindness means being respectful and considerate of others.
  • Transparency means being open and honest about everything.
  • Efficiency means working effectively and avoiding waste.
  • GitLab's values are reflected in their company culture and their products.
  • GitLab's products are designed to be user-friendly and efficient.
  • GitLab's company culture is open and transparent.
  • GitLab employees are encouraged to be themselves and to contribute their ideas.

Why GitLab publicly shares team meetings (00:05:29)

  • GitLab posts videos of team meetings on YouTube.
  • The policy is to be as transparent as possible, excluding customer data and vulnerability information.
  • Team members are encouraged to record and live stream their meetings.
  • Publicly sharing meetings has led to contributions from customers and open-source community members.
  • Developers watching team meetings have noticed and fixed bugs or issues.
  • The decision to share a video is up to the individual and their team.
  • Certain meetings, such as Performance Indicator Reviews and Key Reviews, are not made public due to sensitive information.
  • GitLab's culture of transparency is unique.
  • All team meetings are recorded and uploaded to YouTube, except for those involving sensitive information.
  • This transparency has several benefits:
    • It allows customers and open-source contributors to see what GitLab is working on and contribute their own ideas and solutions.
    • It helps team members learn how to be more effective in meetings.
    • It fosters a sense of community and collaboration within GitLab and beyond.

The GitLab Handbook (00:09:49)

  • The GitLab handbook is available at
  • It contains information about GitLab's mission, vision, strategy, onboarding process, anti-harassment policy, and more.
  • Companies can fork the handbook and use it as a starting point for their own operations.
  • The handbook has been used by startups to create their own UX mission and operating procedures.
  • The handbook can be leveraged to quickly fix or restart something, or to create a new department.
  • The handbook includes competencies for product managers, which can be used to level and ladder teams.
  • GitLab shares a lot of information publicly, including their YouTube videos and handbook.
  • The YouTube videos provide insights into GitLab's culture, values, and practices.
  • The handbook provides detailed information about GitLab's operations, including their mission, vision, strategy, onboarding process, anti-harassment policy, and more.

GitLab’s issue tracker (00:11:30)

  • Majority of issues are public.
  • People with accounts can create and comment on issues.
  • Customers and conference attendees are encouraged to visit the issue tracker to vote and comment on issues.
  • GitLab's transparency has inspired other organizations to do the same.
  • Detailed one-year direction is publicly available.
  • The direction links to the issue tracker, providing insights into how goals will be achieved.
  • GitLab's transparency makes it the most transparent publicly traded company in the world.
  • GitLab's success lies in its execution, not just its ideas.
  • Sharing information openly reduces the fear of ideas being stolen.
  • Despite transparency, GitLab still manages to ship 12 software releases a year, with 149 releases in the last 12 years.

How to successfully build a culture of transparency (00:14:29)

  • Pushing oneself to realize what is truly confidential and what is not.
  • Avoiding artificial silos and storing information in a single source of truth that anyone can access and contribute to.
  • Recording team meetings, leadership team meetings, and even coffee chats to capture valuable information.
  • Transparency should extend to all levels of the company, from team meetings to informal chats.
  • Overly transparent: Sometimes issues or recordings are accidentally made public when they should have been kept private.
  • Learning from mistakes and reinforcing that learning across the team to avoid repeating the same mistakes.
  • The risk of occasional transparency issues is outweighed by the value of pushing for transparency.
  • Start simple by publishing a team meeting and making it available to everyone in the company.
  • Gradually expand transparency to weekly meetings, asynchronous readouts, and other forms of communication.
  • Find the right balance of transparency that works for your company and industry.

Benefits of operating with transparency (00:18:11)

  • Improves focus on results, especially for customers.
  • Allows asynchronous consumption of information, reducing FOMO.
  • Enhances team alignment and uncovers issues early.
  • Encourages transparency as it becomes easier and lessens the burden of remembering details.
  • Facilitates informed decision-making by making information accessible.

The value of building in public (00:19:55)

  • Enhances external engagement, including customer feedback and community contributions.
  • Builds trust with users and customers by providing visibility into the roadmap.
  • Applicable in various industries, even heavily regulated ones, to some extent.
  • Particularly beneficial for tech companies building products with a community component, developer-oriented, or open-source.
  • Can lead to increased customer engagement, retention, and expansion.

How GitLab implements their core value of kindness (00:21:53)

  • Kindness is a core value at GitLab and is practiced by assuming positive intent, treating each other with kindness, and saying thanks and sorry.
  • Negative feedback is given one-on-one to avoid misinterpretation.
  • The "thanks" channel reinforces positive engagement and collaboration.
  • GitLab values transparency and communicates openly about everything happening in the company.
  • Transparency and remote work go hand in hand, as remote work requires clear and specific communication.
  • GitLab's values, transparency, and remote work environment complement each other and have evolved as the company has grown.

What it means to have “short toes” (00:25:16)

  • “Short toes” means focusing on the work and not taking feedback personally.
  • It's about commenting on the work, not the person.
  • Assuming positive intent helps reduce conflict.
  • Short toes prevent feeling like people are stepping on your toes.
  • Contributes to building trust and community.
  • GitLab values kindness, transparency, and short toes.
  • Kindness means being considerate and respectful of others.
  • Transparency means being open and honest about everything.
  • Short toes means focusing on the work and not taking things personally.
  • The speaker describes GitLab as the happiest place they've worked.
  • They attribute this to the company's values and the sense of working together for the common good.
  • GitLab's success shows that it's possible to build a successful business while also making employees happy.

Other core values (00:27:41)

  • Focus on results for customers:
    • Helps the company empathize with customers and the broader community.
  • Efficiency:
    • Drive responsibility down to the lowest level in the organization.
    • Empowers teams to work efficiently and achieve high velocity.
  • Iterate on products based on customer feedback.
  • 30-year mission, 3-year strategy, and 7-year vision.
  • Goal is to become the first all-ops platform and the single source of truth for R&D organizations.
  • Empower teams to achieve the long-term goal in the way they think is best.
  • Structured by sections (Dev, Sec, Ops), stages (create, plan, monitor, verify), groups (lowest level), and categories.
  • Groups manage specific integrations and features.
  • Structure ensures that people who need to work closely together can do so and that stages are tied together to achieve desired outcomes.
  • All information about the company's direction, planning, and meetings is available in the handbook.
  • Cadence for revisiting and planning is also shared.
  • Information is available down to the group level on the marketing site, including links to epics, issues, and tasks.

Common reasons for not fitting in at GitLab (00:32:16)

  • Remote work is not for everyone.
  • Some people miss the in-office experience and daily interactions with colleagues.
  • Lack of human connection can be a challenge for some remote workers.
  • Adjusting to the remote work lifestyle can be difficult for some individuals.
  • GitLab was the largest all-remote company before the pandemic with around 1100 employees.
  • With other companies recalling employees back to the office, GitLab might still be the largest all-remote company.
  • Google and Apple were the largest all-remote companies during the pandemic, but their employees are now returning to the office.

Advice for remote teams (00:34:42)

  • To ensure successful remote work, companies should prioritize transparency, results-oriented work, over-communication, and in-person events.
  • When setting outcomes, focus on measurable results tied to the number of hours worked rather than just shipping features.
  • Celebrate customer adoption of features instead of just shipping them.
  • Shift the focus from deliverables and hours worked to solving customer use cases and pain points.
  • David DeSanto, CPO of GitLab, addresses common questions about their company culture and remote work.
  • People often ask about his transition from software development to product management and how he knew it was the right move.
  • Another common question is about GitLab's transparent handbook and unfiltered communication channels and why they chose to implement these practices.
  • Lastly, people seek advice on whether remote development suits them, and David shares his personal experience transitioning to remote work and its positive impact on his life.

Advice for getting into product (00:42:04)

  • Product management is not the glamorous role people think it is.
  • Product managers are the hub that connects engineering, marketing, sales, legal, etc.
  • A good product manager should push boundaries and challenge the status quo.
  • Product managers should focus on understanding the customer's needs and pain points, rather than simply taking orders.
  • Product management is a lot of work, discussions, and sometimes tension, but it is also the best job.
  • Kindness: Be kind to everyone, even when it's difficult.
  • Transparency: Be transparent about everything, even when it's difficult.
  • Short toes: Don't be afraid to make mistakes.

Advice for PMs who are struggling in a remote world (00:43:52)

  • For remote work, conduct "deep dive interviews" during the hiring process to assess candidates' suitability. This involves having them write requirements and engage in role-playing with engineers.
  • Use communication platforms like Slack or comment on GitLab issues to promptly ask questions or provide feedback.
  • Assume good intent and be kind in communication, especially in remote work settings. Over-communication is encouraged to ensure outcomes are met.
  • GitLab's core values are kindness, transparency, and short toes.
  • Kindness means being respectful and considerate of others, even when you disagree with them.
  • Transparency means being open and honest about everything, even when it's difficult.
  • Short toes mean being humble and willing to admit when you're wrong.

Specific tools that help with remote work (00:48:25)

  • GitLab utilizes its own product, GitLab, for internal communication and collaboration, ensuring customer needs are met.
  • Employees are encouraged to use issues, Slack, and Zoom for effective and transparent communication.
  • The company's handbook serves as a single source of truth for operations and is treated as code, allowing employees to contribute improvements.
  • The handbook outlines the product development lifecycle, expectations, and roles, promoting transparency and accountability.
  • Major changes, such as introducing new product categories or altering the product development framework, require senior leadership approval.
  • Employees are empowered to create their own mini versions of the handbook to provide guidance without dictating direction.
  • Employees have the freedom to achieve their goals as long as they align with the company's objectives.

Time zones and remote work (00:53:13)

  • Focus on asynchronous communication for key decisions involving people in different time zones.
  • Make meetings optional, record them, and provide detailed notes for those in different time zones.
  • Strive for inclusivity, even in leadership roles, by empowering team members to make decisions without requiring overlapping work hours.
  • Embrace geographical dispersion and empower team members to attend meetings that align with their schedules.
  • Utilize note-taking, recorded meetings, and asynchronous communication to ensure inclusivity.
  • Emphasize clear communication, setting clear steps and frameworks for operations.
  • Embrace transparency to ensure people can follow along.
  • Remote work allows for hiring the best person for the role, regardless of location, and provides employees with more flexibility and life options.
  • GitLab has successfully implemented remote work across various roles and divisions, including product management, design, technical writing, research, and more.

Breadth-over-depth strategy (00:57:18)

  • GitLab initially focused on a "breadth over depth" strategy to build out its DevOps platform but later pivoted to a "depth over breadth" approach to enhance specific key areas and accelerate software delivery for companies.
  • Key areas of focus for depth include source code management, code review, IDE experience, remote development, CI/CD, security and governance, planning, and AI.
  • GitLab's success as the leading DevOps platform is attributed to finding key areas where it can truly help customers accelerate software delivery.
  • Similar to HubSpot, GitLab emphasizes transparency as one of its core values, sharing financial information with all employees.
  • GitLab's AI strategy involves identifying areas where AI can enhance their core offerings while maintaining their leading position in the industry.

AI at GitLab (01:04:14)

  • GitLab's unique approach to AI in software development focuses on the entire software development lifecycle, benefiting teams beyond developers.
  • GitLab prioritizes transparency and privacy with AI, making models source-available and not using customer intellectual property for training.
  • GitLab aims for AI efficiencies, with GitLab Ultimate offering a 7x boost in productivity and a goal to reach 10x.
  • GitLab uses a combination of GitLab-created open-source and commercial models from partners like Google and Anthropic.
  • GitLab acquired Unreview, a company that provides proprietary AI models, in early 2021 or 2022.
  • GitLab explores leveraging open-source AI models and contributing back to the open-source community.
  • GitLab's AI model validation team ensures the ethical use of AI at scale and selects appropriate models for their products.
  • GitLab's partnerships with Google Cloud and Anthropic meet the company's privacy requirements.
  • David DeSanto, GitLab's CPO, uses humor to navigate high-stakes conversations and executive negotiations, helping to defuse tension and keep people moving forward.
  • GitLab has expanded its offerings beyond source code management and code review to include security, governance, remote development, and enterprise agile planning capabilities.
  • Customers have reported efficiency boosts of 50% and above by leveraging GitLab Duo, which combines GitLab's development and operations platforms.

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

  • GitLab offers a wide range of products and solutions across the software development lifecycle.
  • Key strengths include SCM, code review, CI/CD, security and compliance, monitoring, value stream management, analytics, and product analytics.
  • GitLab is currently expanding into observability and service management.
  • GitLab provides an amazing experience, from idea generation to running in production, with features such as planning functionality and enterprise digital planning solutions.

Lightning round (01:14:54)

  • David DeSanto recommends "Crossing the Chasm" by Jeffrey Moore and "Essentialism" for understanding business strategy and prioritization. He also suggests the Critical Core Context framework for focusing on what's essential.
  • His favorite recent TV show is "The Devil's Hour," and his favorite movie is "The Glass Onion."
  • He prefers the STAR method for asking interview questions to assess problem-solving skills.
  • His favorite new product is Arc browser for its organization and tab management features.
  • His life mottos include:
    • As a leader, your team's accomplishments are theirs, but their failures are yours.
    • "Just make it work," inspired by Tim Gunn's saying from Project Runway.
    • "It's just software, so anything's possible," a reminder that solutions can be found for any software-related challenges.
  • GitLab's culture emphasizes kindness, transparency, and a "short toes" approach, which encourages employees to be humble and open to feedback.
  • To connect with David DeSanto, visit GitLab's social media pages or search for him on LinkedIn as "Danto" or on X as "davidor Danto."
  • Listeners can support GitLab by providing feedback, contributing to the handbook or codebase, or spreading the word about GitLab.

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