Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase)

1. Design for Complex Use Cases

Instead of optimizing for MVPs, design for the most complex use cases first. Understand simple scenarios, but ensure technical and product design accommodates future global, complex scenarios, even if not supported initially, to prevent costly architectural rework.

2. Become World Expert First

As a product leader, personally go deep and become the world expert in your product’s domain before delegating to specialists. This foundational understanding is crucial for effective product thinking.

3. Dedicate Half Time to Deep Understanding

Dedicate significant time (e.g., 50% of your work week) to personally “going and seeing” and deeply understanding the product and its domain firsthand.

4. Implement “Imperatives” for Focus

Implement “imperatives” – a short, force-ranked list of 10-ish cross-team priorities that everyone in product and engineering must factor into their work. Crucially, clarify what is not on the list to enhance focus and clarity.

5. Immediate Decision-Making Culture

Foster a culture of immediate decision-making by avoiding delays. Make decisions on the spot, or immediately bring in necessary people (e.g., via Slack call) to resolve issues the same day.

6. Clarify Priorities (and Non-Priorities)

Top-level product decision-makers must be extremely clear about what the priorities are and, crucially, what they are not. This eliminates distractions and focuses the team on the core mission.

7. Small Teams, Clear Missions

To maintain velocity at scale, organize into small teams with clear missions. Break down large problems into sufficiently small bits for these groups to attack wholeheartedly, minimizing horizontal communication.

8. Invest in Clear Platform

Build and invest in a clear, easy-to-use platform with a well-defined interface. This reduces decision-making complexity for both engineers and product people working on domain-specific problems.

9. Expand Internationally Early

Start international expansion earlier than you think necessary. It is consistently harder, more specialized, and takes longer to absorb cultural lessons than anticipated.

10. Respect Unique Local Contexts

When expanding internationally, deeply respect and adapt to each country’s unique local context and cultural nuances. Avoid simply porting a domestic approach, as this can be perceived as insulting and undermine credibility.

11. Process Supports Deep Thinking

Avoid using process as a substitute for deep product thinking. Implement just enough process to create a framework for good decisions, but no more.

12. Cultivate Humility as PM

For early career PMs, cultivate humility and acknowledge that no one has all the answers in product development. Be open to absorbing new information, synthesizing it, and changing conclusions.

13. Maintain Curiosity, Elasticity

Maintain curiosity, elasticity of thought, and creativity throughout your product career. Avoid closing yourself off to new ideas or assuming you always have the right answer.

14. Leaders Model Fast Decisions

For a culture of fast decision-making, senior leadership (especially the founder/CEO) must deliberately model this behavior constantly across all interactions (Slack, meetings, in-person).

15. Strict Decision Deadlines

Implement and strictly adhere to firm timelines for decision-making in planning processes (e.g., quarterly planning). Move on if decisions aren’t made by the deadline to reinforce a culture of rapid execution.

16. Product Managers: World Experts

Expect product managers to become the world’s foremost experts in their product domain. This deep expertise enables them to make quick, informed decisions without extensive follow-up.

17. Clear Product Leadership

Product leadership must be extremely clear and precise about what needs to be done. This clarity, combined with platform investment, enables teams to accelerate their execution over time.

18. Recalibrate Team Skills

Continuously assess and recalibrate team composition, ensuring the right distribution of experience and seniority. Match individuals to tasks they love and excel at, especially as product needs evolve from zero-to-one to scaling.

19. Launch New Products with Entrepreneurial Engineer

For new product lines, find an entrepreneurial engineer (internal or external) capable of product thinking, pair them with a design partner, and have them recruit a small 2-4 person team to build and launch the product in 6-9 months.

20. Direct Senior Leadership Exposure

Ensure senior leadership is directly exposed to what’s happening at all levels of the organization, bypassing management layers when necessary. This fosters transparency and enables quicker feedback and decision-making.

21. Debate, Then Commit

In uncertain environments with strong opinions, encourage open debates to explore options. Once a decision is made, establish a clear company point of view and commit to it fully until a new direction is chosen.

22. Product Leaders Must Be Right

Product leaders must strive to be right most of the time, especially in ambiguous situations with incomplete information, as their decisions significantly impact the entire organization’s time and energy.

23. Leaders Change Minds, Admit Wrong

Great leaders are willing to change their minds based on new information and admit when they are wrong. Foster an environment where it’s safe for everyone to acknowledge mistakes and adapt.

24. Adapt to Strong-Opinion Founders

When working with a strong-opinionated founder, be adaptable and understand the dynamics of the relationship. Ensure the founder is open to being challenged and build a deep foundation of mutual respect.

25. Prioritize Global Markets Systematically

Prioritize international markets by first identifying immediate customer demand. Then, assess the difficulty and strategic value of building in each country, and finally consider risks and long lead times. Stack rank and revisit this list.

26. Prioritize Security, Customer Money

During periods of rapid growth and market frenzy, leaders should focus the team on security and protecting customer money, rather than discussing personal wealth. This grounds the team in core responsibilities.

27. Balance Immediate, Long-Term

Address immediate issues (e.g., site outages) while simultaneously setting a clear, long-term vision (e.g., 6-month goals) for product and backend to guide the team’s efforts.

28. Reflect on Stressful Periods

When experiencing intense, stressful work periods, take time to step back and talk with friends to gain perspective. Frame these experiences as opportunities for significant personal growth and learning for the future.

29. Use Complex Case Studies (Hiring)

In PM interviews, use complex case studies that are too large for upfront answers. This allows candidates to react to ad hoc questions or changing assumptions, revealing mental agility and deep problem understanding.

30. Value Insightful Candidate Questions

Pay close attention to the quality and insightfulness of questions candidates ask. Truly insightful questions, especially those that make you pause and think, are strong indicators of a good candidate’s interest and deep thinking.

31. Ask “What Questions Do You Have?” (Hiring)

Always ask candidates “What questions do you have for me?” early in the interview process. Their questions reveal the depth of their thinking, interest, and engagement in the role.