Leading with empathy | Keith Yandell (DoorDash, Uber)
Executive Summary
Keith Yandell joins Lenny Rachitsky to discuss working documents, career support, empathy in disagreements and constructive feedback. Selected coverage omits COVID, business-development/product and later tough-times sections. Company examples and claimed effects are his account, unverified here. Untimed topics are editorial, not video chapters.
Key Takeaways
Write down how to work with you
Yandell created a document to help new people understand expectations as the organization grew. It covers traits he values, feedback on his own behavior and commitments to the team. A useful version explains actual working habits rather than only aspirational values.
Name what you are working to improve
He describes feedback that his habit of arguing to test conviction could confuse people about what he supported. Explaining that habit made it easier to understand him, while acknowledging it was something to improve. Transparency should accompany change, not excuse confusing behavior.
Make career conversations part of the agenda
He reserves the last part of one-on-ones for career development and offers to help people find their next job, even outside the company. He argues that this can encourage honest conversations and reduce surprise departures. His outcomes are personal experience, not a guaranteed retention strategy.
Understand the motivations behind a disagreement
Yandell defines empathy as understanding how people are measured and what experiences they bring. Growth and profitability leaders may have valid but conflicting aims. Make each person feel heard before treating the disagreement as a failure to cooperate.
Have each side argue the other case
In a trade-off discussion, he asks the profitability side to give the strongest reasons for growth, or the reverse. He says this can build empathy and sometimes change a participant's mind. The purpose is an honest account of the opposing reasoning, not a weak version built to dismiss it.
Set a decision owner and time horizon
If debate repeats without reaching consensus, identify who will break the tie and when the decision must be made. Yandell says the owner varies with the decision rather than always being the CEO. Hearing everyone out does not require allowing the meeting to continue indefinitely.
Ask for constructive feedback before giving yours
His one-on-one approach explicitly expects constructive feedback for the manager before the manager gives feedback. He recalls Uber's T3 B3 exercise as three positives and three constructive points. This is his account of a practice, not a verified current company policy.
The Conversation Breakdown
Write down how to work with you
⏱ Untimed topicYandell created a document to help new people understand expectations as the organization grew. It covers traits he values, feedback on his own behavior and commitments to the team. A useful version explains actual working habits rather than only aspirational values.
Name what you are working to improve
⏱ Untimed topicHe describes feedback that his habit of arguing to test conviction could confuse people about what he supported. Explaining that habit made it easier to understand him, while acknowledging it was something to improve. Transparency should accompany change, not excuse confusing behavior.
Make career conversations part of the agenda
⏱ Untimed topicHe reserves the last part of one-on-ones for career development and offers to help people find their next job, even outside the company. He argues that this can encourage honest conversations and reduce surprise departures. His outcomes are personal experience, not a guaranteed retention strategy.
Understand the motivations behind a disagreement
⏱ Untimed topicYandell defines empathy as understanding how people are measured and what experiences they bring. Growth and profitability leaders may have valid but conflicting aims. Make each person feel heard before treating the disagreement as a failure to cooperate.
Have each side argue the other case
⏱ Untimed topicIn a trade-off discussion, he asks the profitability side to give the strongest reasons for growth, or the reverse. He says this can build empathy and sometimes change a participant's mind. The purpose is an honest account of the opposing reasoning, not a weak version built to dismiss it.
Set a decision owner and time horizon
⏱ Untimed topicIf debate repeats without reaching consensus, identify who will break the tie and when the decision must be made. Yandell says the owner varies with the decision rather than always being the CEO. Hearing everyone out does not require allowing the meeting to continue indefinitely.
Ask for constructive feedback before giving yours
⏱ Untimed topicHis one-on-one approach explicitly expects constructive feedback for the manager before the manager gives feedback. He recalls Uber's T3 B3 exercise as three positives and three constructive points. This is his account of a practice, not a verified current company policy.
Core Frameworks & Ideas
How-to-work-with-me document
Describe expectations, your improvement areas and commitments to the team.
Opposing-case decision method
Ask each side to make the other's strongest case, then clarify the decision owner and deadline.
T3 B3 feedback
Yandell recalls three positive and three constructive points as a way to normalize feedback upward.
Actionable Next Steps
- ✓Write a working document that includes one real improvement area.
- ✓Reserve time in the next one-on-one for career development.
- ✓In a disagreement, ask each side for the strongest opposing reasons.
- ✓Ask for constructive feedback and state who owns the final decision.
Notable Quotes
“I think that, for me, it all comes down to empathy.”
“And I think it's really important to make each person feel heard.”
“If you create a space where you require constructive feedback, it's a lot easier to give feedback.”
The One Thing to Remember
Make expectations explicit, hear the other side and make feedback a normal part of working together.