Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more

1. Cultivate Second-Order Thinking

Develop the ability to foresee how today’s decisions will impact future choices and the overall system, as this long-term perspective saves significant time and money by preventing constant rebuilding and ensuring scalable product development.

2. Distinguish Decision Types

Categorize decisions as “one-way doors” (hard to reverse, requiring extensive discussion and buy-in) or “two-way doors” (reversible, allowing teams autonomy and faster movement), dedicating appropriate time and resources based on their impact.

3. Collaborate on Vision & Strategy

Involve your team in the vision and strategy-setting process from the beginning, as bringing people along on the journey fosters buy-in and makes execution more effective, even if the final decision rests with a clear leader.

4. Apply Strategy Pyramid Framework

Utilize the Vision-Mission-Strategy-Objectives pyramid framework to structure your long-term direction, progressively clarifying how the mission supports the vision, how strategy enables the mission, and how objectives (like OKRs) translate strategy into actionable short-term goals.

5. Implement Shared Goal Frameworks

Adopt a shared goal framework (like OKRs or similar) across all functions, regardless of business size, to clearly articulate strategy and translate it into actionable, short-term steps, ensuring team alignment and progress.

6. Optimize Onboarding for First Success

For marketplace products, prioritize getting new users (e.g., sellers) to their first successful interaction (e.g., first sale) quickly, even if it means adding friction to the onboarding flow, as early success is a huge long-term motivator.

7. Balance Growth with Quality Metrics

When building early products, pick quality metrics (like review rates) that balance or conflate with growth metrics and use them as a North Star to ensure the entire team understands the ultimate goal of delivering a great customer experience.

8. Integrate Second-Order Thinking

Integrate prompts for second-order thinking into product documentation templates (e.g., PRDs) and establish clear first principles for changes, forcing teams to consider long-term impacts and align on foundational elements before building.

9. Utilize Three Check-in Gates

Establish three key check-in points for product development: first principles (what to build, what problem to solve), approach/technical review (how to build it), and pre-shipment readiness, ensuring alignment and quality at critical stages.

10. Unify Product Review Meetings

Consolidate functional reviews (design, technical) into a single, cross-functional product review meeting to ensure all stakeholders are present, receive the same feedback, and align on strategic approvals, preventing isolated feedback and improving team cohesion.

11. Practice Empathetic Decision Alignment

When seeking alignment on decisions, use empathy by actively listening to your team’s concerns, repeating their points back to them to ensure they feel heard, and understanding their reasoning before guiding them or adjusting your approach.

12. Seek Leadership Context for Strategy

Engage with leadership and business leaders early in the strategy-setting process to gain crucial organizational context, avoiding conflicts with existing strategies or technical limitations later on.

13. Conduct Weekly Strategy Check-ins

Hold regular weekly team meetings to cascade leadership feedback, consistently review your team’s vision and strategy, and assess progress towards goals, which helps maintain buy-in and reduces distractions from new priorities.

14. Share Leadership Feedback Swiftly

After leadership reviews, quickly record and share updates (e.g., using Loom) summarizing feedback and any resulting changes with your team via Slack, maintaining a tight feedback loop and keeping everyone informed and excited.

15. Dogfood Your Product Regularly

Consistently use your own product (dogfooding) to personally experience its quality and quickly identify areas that need improvement, providing direct motivation for teams to act on fixes.

16. Structure Remote Brainstorming Sessions

For remote brainstorming, pre-fill your digital whiteboard (e.g., Miro, FigJam) with discussion headers, include a pre-read (e.g., competitive landscape) in the invite, and use timers during the session to guide discussion and synthesis.

17. Decouple Ideation from Finalization

During visioning or brainstorming sessions, focus on generating ideas and synthesizing similar concepts rather than immediately finalizing a vision; draft it later and gather more feedback before making it final.

18. Embrace Asynchronous Communication

Adapt to remote work by utilizing asynchronous tools like Slack (for updates and huddles) and digital whiteboards (Miro, FigJam) to reduce reliance on synchronous meetings, keep teams informed, and facilitate collaboration across different time zones.

19. Track Energy Levels in Meetings

After meetings, color-code them (red for draining, yellow for neutral, green for energizing) on your calendar to reflect your energy levels, helping you understand what work excites you and optimize for those activities in future roles.

20. Align Work with Personal Energy

Reflect deeply on what aspects of your role as a product person give you the most energy and excitement, then actively seek out or shape your next opportunities to optimize for those specific activities and challenges.

21. Actively Consume New Products

Regularly download, try, and use new products and apps as a consumer, as this active engagement with diverse digital experiences enhances your understanding and makes you a more insightful product builder.

22. Diversify Your Information Feed

Expand your social media and information sources beyond just tech-focused individuals to include cultural journalists or those plugged into the broader zeitgeist, ensuring you understand the current cultural context for better product marketing and messaging.