Leading with empathy | Keith Yandell (DoorDash, Uber)

1. Persevere as a Founder

If you believe in your business, maintain an unwavering drive to keep going, as it only takes one ‘yes’ despite numerous rejections. This resilience is critical for overcoming challenges like low runway and being told no by many.

2. Embrace Tough Times

Leverage challenging periods to identify mission-driven team members, enforce financial discipline by focusing on unit economics, and attract top talent. Crises also create a valuable singularity of focus within the company, which talented people often appreciate.

3. Foster Customer Empathy

Implement mandatory programs like ‘WeDash’ (doing deliveries) or customer support shifts for all employees at least four times a year to build empathy and keep the team close to the product experience. This practice also serves as a governor to attract customer-obsessed talent during hiring.

4. Lead Diverse Teams with Generalists

For 10x outcomes, consider hiring generalists to lead new functions, then empower subject matter experts by getting out of their way. Be transparent about your lack of expertise and focus on helping your expert hires be successful.

5. Scale Culture with Written Docs

Create a ‘How to Work With Me’ document detailing your expectations, traits of successful team members, areas you’re improving on, and commitments to your team. This scales culture and helps new hires acclimate quickly to a fast-paced environment.

6. Proactively Support Career Growth

Commit to helping your team find their next job, even if it’s outside the company, by discussing career development in one-on-ones and forwarding relevant opportunities. This fosters transparency, aids backfilling, and builds a strong long-term reputation as a manager.

7. Drive Effective Decision-Making

When facing complex trade-offs, foster empathy by asking each side to argue the opposing viewpoint (steel-manning). Clearly define the decision-maker and a timeline, then ensure the team ‘debates and commits’ to the final decision.

8. Cultivate a Feedback-Rich Culture

Demand constructive feedback from your team in one-on-ones, using structured systems like ‘T3B3’ (three positives, three constructive points). Always thank them enthusiastically for the feedback and visibly action it to build trust and show progress.

9. Prioritize Urgency & Compound Gains

Continuously push to ship products faster, even by small margins, understanding that these compounded gains will allow you to outpace competitors over time. Challenge the need for excessive testing to maintain momentum and achieve 1.01x returns.

10. Maintain Hunger, Avoid Complacency

After achieving milestones, quickly refocus on the next challenge rather than prolonged self-congratulation. Staying hungry prevents falling behind competitors who are continuously working to improve and innovate.

11. Strategic BD-Product Collaboration

Give the product team early visibility into the BD pipeline to gauge impact, but avoid bringing them into full discussions too early to prevent wasted cycles. Prioritize building scalable platforms for partnerships rather than bespoke solutions for each deal.

12. Test Deals with Operations First

Before expending significant product resources on new partnerships, use ‘hacky operations’ or simple tests (e.g., promo codes) to validate the customer behavior thesis. This aligns with the ‘dream big, start small’ and ‘do things that don’t scale’ philosophies to avoid wasted product work.

13. Product Leaders: Understand Law

For consumer-facing products, develop a general understanding of relevant regulations and constraints. Engage with legal teams with curiosity, applying a first-principles mindset to push for less conservative interpretations and be accretive to the business.

14. Build Investor Trust with Realistic Projections

When fundraising, present highly confident numbers that you know you will hit, rather than aspirational stretch plans. This builds long-term trust with investors, which is more valuable than short-term valuation gains or dilution.

15. Use Direct Interview Feedback

If a candidate has strong qualifications but raises cultural concerns, provide direct feedback during the interview process (e.g., ‘You seemed like an asshole’). This tests their self-awareness and how they handle criticism, revealing their true culture fit.