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

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.