10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

1. Maintain Perspective, Play Hard

While pursuing intense effort and extraordinary outcomes, maintain perspective by remembering the brevity and insignificance of life, allowing for levity, and playing the ‘sport of business’ with full effort but without forgetting it’s just a game.

2. Know When to Quit

Don’t fall for the ’never quit’ venture capital propaganda; if product-market fit isn’t clearly evident after 2-3 pivots or 4-5 years, be willing to quit, reset, and start anew.

3. Embrace Discomfort for Results

To achieve 99th percentile outcomes, expect and embrace discomfort and exhaustion at work, as being in a comfort zone indicates a mistake and a lack of extraordinary effort.

4. Mirror CEO’s Intensity

As a leader, mirror the founder CEO’s intensity and ambition, rather than buffering team members from demands, to preserve high energy levels throughout the organization and prevent dysfunctional drop-offs.

5. Inject Energy, Fight Entropy

Recognize that systems naturally tend towards disorder (entropy); continuously inject energy into your organization to fight decay, maintain quality, and achieve extraordinary outcomes.

6. Always Give Feedback

Never withhold feedback that could help someone improve, as optimizing for your own comfort by avoiding uncomfortable conversations is fundamentally selfish and detrimental to high-performance teams.

7. Escalations Are Gifts

View customer escalations as valuable gifts that provide direct insights into problems, allowing for process iteration and system improvement, and never consider them an inconvenience.

8. Product is High-Order Bit

Recognize that product excellence is the ‘high order bit’ for business success; getting the product right simplifies every other function, including finance, sales, marketing, and recruiting.

9. Don’t Market Product-Market Fit

Understand that market demand (binding receptors) for your product either exists or it doesn’t; marketing cannot create product-market fit if the fundamental need isn’t there.

10. Apply Process Judiciously

Apply processes judiciously to lower ‘beta’ (volatility) in areas requiring reliability (e.g., payroll) without suppressing ‘alpha’ (creativity, outperformance) in areas needing innovation (e.g., zero-to-one product building).

11. Lead From The Boiler Room

As an executive, avoid making decisions from a distance; instead, immerse yourself in the ‘boiler room’ to study systems bottom-up and develop informed hypotheses for improvement.

12. Fight Local Comfort

As a leader, actively fight the natural tendency of teams to optimize for local comfort over company outcomes by relentlessly injecting energy and demanding high performance.

13. Join Winning Teams

To maximize learning and growth, prioritize joining winning teams and successful companies, as observing success provides more informative lessons than learning from mistakes.

14. Ask For Relevant Experience

When seeking guidance, ask people for their relevant experience rather than just advice, as this helps filter for genuinely informed perspectives and avoids generic, ungrounded opinions.

15. Dedicated Root Cause Escalations

Create a dedicated escalations team skilled at digging deep to uncover the real root causes of issues, tracing problems back through software and systems to solve them fundamentally, not just superficially.

16. Deliberately Understaff Projects

Deliberately understaff every project at the company to avoid politics, working on low-priority items, waste, slowdowns, and cruft.

17. Prioritize Foundational Work

When fixing a dysfunctional team or product, prioritize foundational work and address issues in their correct order, leading bottom-up from specific observed circumstances.

18. Develop Versatile Executive Skills

Strive to be a versatile executive who can be ’tossed into any challenge’ and bring order to chaos, fixing problems across various functions.

19. Create Cultural Vessels

To drive cultural change, create unique, memorable ‘vessels for meaning’ (like the ‘pickle’ for product quality) and consistently fill them with your desired meaning to foster common parlance and stick in people’s minds.

20. Test Understanding, Avoid Jargon

When evaluating someone’s understanding of a concept, ask them to explain it without using the specific jargon or buzzwords, which forces them to break it down and demonstrates true comprehension.

21. Use Challenging Case Studies

Implement a single, extraordinarily difficult case study for all product candidates, regardless of seniority, to assess their problem-solving depth, adaptability, and non-defensiveness when given new information, even if they don’t fully solve it.

22. Address Every Bug Publicly

As an executive, address every bug or issue you encounter by dropping it at the feet of the responsible manager, preferably in public, to model intensity and prevent entropy.

23. Conduct Backchannel References

Insist on conducting backchannel reference checks for every hire, as it’s a critical step that should never be skipped to ensure quality and fit.

24. Demand 99th Percentile Energy

When processes become routine or boring, demand 99th percentile energy from yourself and your team to prevent entropy from creeping in and causing system decay.

25. Model Intense Public Feedback

Actively participate in public feedback channels for products, modeling intense, direct, and questioning feedback to encourage transparency and continuous improvement from the team.

26. Publicly Review Product Flows

Implement a process where major product flows are recorded (e.g., Loom videos) and personally review each one, providing feedback in public channels to educate and align other product and engineering managers.

27. Embrace Founder Idiosyncrasies

Recognize that successful companies often thrive due to the unique idiosyncrasies and specific strengths of their founders, which great investors learn to spot and back.

28. Seek Great Product Managers

If you have a negative view of product managers, it’s likely you haven’t worked with a truly great one, so seek out and appreciate the value a skilled PM brings to a team.

29. Use AI for Language

Utilize AI tools like ChatGPT or Gemini as a non-judgmental thought partner to refine language and find pithy ways to articulate crisp ideas, especially for communicating complex concepts, even if only 20% of its output is useful.