The GitLab way: Kindness, transparency, and short toes | David DeSanto (CPO)
David DeSanto, Chief Product Officer at GitLab, discusses their unique culture of transparency, effective remote work strategies, and core values like kindness and 'short toes.' He also shares insights on product strategy (breadth vs. depth) and their approach to AI across the SDLC.
Deep Dive Analysis
16 Topic Outline
GitLab's Unique Culture of Transparency
Policy and Benefits of Publicly Shared Team Meetings
The Public GitLab Handbook and Issue Tracker
Building a Culture of Transparency: Challenges and Benefits
GitLab's Core Values: Kindness and Short Toes
Focus on Results and Efficiency as Core Values
GitLab's Long-Term Vision and Organizational Structure
Common Reasons for Not Fitting In at GitLab
Advice for Successful Remote Work
Advice for Product Managers Struggling in Remote Environments
Tools and Communication Strategies for Remote Work
Time Zone Management in an All-Remote Company
GitLab's Shift from Breadth-Over-Depth to Depth-Over-Breadth Strategy
GitLab's Unique Approach to AI in Software Development
Leveraging Humor in High-Stakes Conversations
Overview of GitLab's Product Offerings
6 Key Concepts
Transparency Culture
GitLab operationalizes transparency by publicly sharing team meetings on YouTube, maintaining an extensive public employee handbook, and making its issue tracker largely public. This approach aims to foster external contributions, community feedback, and internal alignment by making information accessible to everyone.
Short Toes
This GitLab core value means focusing on the work itself, not taking feedback or contributions personally. It encourages individuals to view comments as attempts to improve the work, rather than personal criticism, reducing negative headbutting in an asynchronous, remote culture.
All-Ops Platform
GitLab's long-term strategic goal to become the single source of truth for R&D organizations, encompassing not just product, UX, engineering, and infrastructure, but also supporting teams like legal, sales, marketing, and compliance across the entire software development lifecycle.
Breadth-over-Depth Strategy
An initial product strategy where a company builds a wide range of functionalities across a platform without necessarily being the absolute best in each area. This approach helps find market fit and differentiate by covering various parts of a workflow, as GitLab did for DevSecOps.
Depth-over-Breadth Strategy
A product strategy adopted after establishing a broad platform, focusing on making key, strategic areas exceptionally strong. This allows the company to accelerate software delivery in critical domains, with the expectation that improvements in deep areas will positively impact surrounding, less-deep functionalities.
Dogfooding
The practice of an organization using its own products internally for all its operations. GitLab uses its own product for everything it does, ensuring the product works for its customers and end-users and providing direct feedback for continuous improvement.
8 Questions Answered
GitLab's policy is to be as transparent as possible, heavily encouraging teams to record and sometimes live stream meetings to their YouTube channel ('GitLab Unfiltered'), unless it involves customer data or vulnerability information.
Benefits include external contributions from customers and open-source community members, valuable feedback, better internal alignment, increased focus on results, reduced FOMO for remote employees, and faster informed decision-making due to accessible information.
Kindness is practiced by encouraging positive intent in communication, having 'short toes' (not taking things personally), and ensuring negative feedback is always delivered one-on-one to avoid misinterpretation in asynchronous interactions.
The most common reason is that the all-remote lifestyle is not for everyone; some individuals miss the in-office, in-person connection and struggle with the adjustment to a fully distributed work environment.
Key advice includes being transparent, focusing on results rather than hours worked, over-communicating, and making time for in-person events to foster human connection among team members.
PMs should write clear, concise requirements, not wait to ask questions or provide updates, and proactively engage digitally on communication platforms like Slack or issue trackers to avoid delays and ensure alignment.
GitLab prioritizes asynchronous communication, ensures key decisions involving DRIs in different time zones wait for their input, makes meetings optional with good notes and recordings, and empowers leaders in various time zones to cover meetings.
GitLab's AI strategy focuses on applying AI across the entire software development lifecycle (not just coding), ensuring transparency and privacy (not using customer IP for training), and finding the right AI model for each specific use case to maximize efficiency gains.
14 Actionable Insights
1. Embrace Radical Transparency
Publicly share team meetings (on platforms like YouTube), internal handbooks, and issue trackers, unless it involves customer data or vulnerabilities. This fosters external contributions, community feedback, and internal alignment, ultimately increasing productivity and customer trust.
2. Prioritize Kindness and Positive Intent
Actively practice kindness and assume positive intent in all communications, especially in remote settings where tone can be misread. Give negative feedback one-on-one to avoid public misinterpretation and foster a more collaborative, less tense environment.
3. Cultivate “Short Toes” Mindset
Adopt a “short toes” approach, meaning you focus feedback on the work itself, not the individual. This prevents feeling personally attacked when receiving criticism and reduces negative headbutting, especially crucial in remote, asynchronous environments.
4. Optimize Remote Work with Key Principles
For effective remote work, prioritize transparency, focus on measurable outcomes over hours worked, practice over-communication, and schedule regular in-person team gatherings. These practices foster connection, clarity, and productivity in a distributed environment.
5. Define Outcomes by Customer Adoption
Shift focus from tracking hours or feature deliverables to defining measurable business outcomes tied to customer adoption and problem-solving. Celebrate the impact and adoption of solutions, not just their shipment, to align work with true customer value.
6. Maintain a Public, Living Handbook
Treat your company handbook as a single source of truth for operations, encouraging all employees to submit merge requests to improve clarity or efficiency. This empowers teams with guidance, not just direction, and ensures everyone understands company processes and expectations.
7. Prioritize Asynchronous Communication
Adopt an “asynchronous first” communication strategy, especially for globally distributed teams, to ensure inclusivity across time zones. Record all meetings and provide thorough notes, and defer key decisions until all Directly Responsible Individuals (DRIs) can contribute.
8. PMs: Clear Requirements & Proactive Communication
Product Managers in remote settings must write exceptionally clear and refined requirements from the outset to prevent misunderstandings. Additionally, proactively communicate and ask questions immediately if concerns arise, avoiding delays from waiting for scheduled check-ins.
9. Implement AI Broadly and Specifically
Integrate AI across the entire software development lifecycle to benefit all teams, not just developers. Prioritize transparency and privacy by disclosing models and training data, and crucially, select the right AI model for each specific use case to maximize quality and efficiency, rather than forcing one model for all tasks.
10. Strategically Balance Product Breadth
Initially, pursue a “breadth over depth” strategy to explore the market, find your niche, and build out a comprehensive platform. Once market fit is established and key areas are identified, pivot to “depth over breadth” by investing deeply in core differentiating areas, leveraging them to uplift other offerings.
11. Adopt a Proactive PM Mindset
Embrace the product manager role as a central hub, pushing boundaries and challenging assumptions to lead effectively. Avoid being an “order taker” by synthesizing requests into core customer pain points and use cases, driving strategic product direction.
12. Leaders: Own Team’s Failures
As a leader, attribute your team’s accomplishments to them, but take personal responsibility for their failures and misses. This fosters a supportive environment and builds trust within the team.
13. “It’s Just Software” Mindset
When facing technical challenges or perceived limitations, remember “it’s just software; anything’s possible.” This mindset encourages creative problem-solving and pushes teams to find solutions rather than accepting limitations.
14. Use Humor to Defuse Tension
In high-stakes or tense conversations, strategically use humor to lighten the mood and disarm the topic. This can help deflate tension, improve morale, and enable people to move forward more productively.
6 Key Quotes
If everyone's really annoyed at you, you're probably actually doing your job well.
David DeSanto
It's about the work. It's not about you.
David DeSanto
We get people who then contribute because of what they see. Oh, I can go build that. I know what that is.
David DeSanto
I think the risk of that occasionally happening is way below the value of actually pushing yourself to do it.
David DeSanto
If you think you're communicating a hundred percent accurately, that's probably 60 or 70% for the other person and shoot for like 150%.
David DeSanto
It's just software. So anything's possible.
David DeSanto
2 Protocols
GitLab Deep Dive Interview Process
David DeSanto- Candidates can write requirements for any chosen topic (e.g., bicycles), not necessarily a GitLab feature.
- Candidates have an hour-long Zoom call with a product person (playing an engineer) to discuss and talk through the requirements.
- Candidates then write the epic (higher-level vision) and the first milestone/MVC (minimum viable change) for their chosen topic.
- The product person asks follow-up questions on the issue, allowing the candidate to refine or better define aspects of their requirements.
GitLab Handbook Update Workflow
David DeSanto- Identify an inefficiency, unclear workflow, or error in the handbook (e.g., typo, poorly worded sentence).
- Open a merge request (MR) to propose the change, even during onboarding.
- For significant changes (e.g., new product category, changes to product development framework), follow defined approval processes, which may require sign-off from CPO, CTO, and other relevant leaders.
- Individual teams can create mini-versions of workflows or guidance, referencing the main handbook, to provide specific direction for their area while aligning with company-wide principles.