Leading with empathy | Keith Yandell (DoorDash, Uber)
Keith Yandell (guest), Lenny Rachitsky (host)
In this episode of Lenny's Podcast, featuring Keith Yandell and Lenny Rachitsky, Leading with empathy | Keith Yandell (DoorDash, Uber) explores doorDash’s Keith Yandell on empathy, culture, and crisis leadership Keith Yandell, longtime DoorDash executive and former Uber litigator, shares how empathy, humility, and founder-led urgency shape DoorDash’s culture and decision-making. He describes practices like the ‘no asshole’ rule, mandatory employee dashing (WeDash), and his “How to work with Keith” doc as core tools for scaling culture through hyper-growth. Yandell explains how a generalist mindset enabled him to lead disparate functions—legal, HR, marketing, support, BD, and corp dev—by hiring experts, giving them autonomy, and then getting out of their way. He also covers leading through crises (near-bankruptcy, COVID), partnering effectively with product, and his unusually proactive approach to developing people—even helping them find jobs outside the company.
DoorDash’s Keith Yandell on empathy, culture, and crisis leadership
Keith Yandell, longtime DoorDash executive and former Uber litigator, shares how empathy, humility, and founder-led urgency shape DoorDash’s culture and decision-making. He describes practices like the ‘no asshole’ rule, mandatory employee dashing (WeDash), and his “How to work with Keith” doc as core tools for scaling culture through hyper-growth. Yandell explains how a generalist mindset enabled him to lead disparate functions—legal, HR, marketing, support, BD, and corp dev—by hiring experts, giving them autonomy, and then getting out of their way. He also covers leading through crises (near-bankruptcy, COVID), partnering effectively with product, and his unusually proactive approach to developing people—even helping them find jobs outside the company.
Key Takeaways
Use directness and feedback to test for cultural fit early.
The story of calling a VP of Engineering candidate an “asshole” and then hiring him anyway shows how blunt feedback surfaces true character; how a candidate responds to tough, honest input is often more revealing than the interview itself.
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Scale culture with explicit, written expectations and self-critique.
Keith’s “How to Work with Keith” document outlines his expectations, quirks, growth areas, and commitments, which accelerates trust, reduces onboarding friction, and attracts high-caliber talent who value transparency and autonomy.
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Generalists can unlock 10x outcomes by rethinking default playbooks.
Tony Xu pushed Keith into non-legal roles with the thesis that experts often reproduce existing patterns; a thoughtful generalist, paired with strong functional leaders, is more likely to challenge constraints and redesign systems from first principles.
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Build deep loyalty by prioritizing your reports’ careers over your org.
Keith explicitly commits to helping people find their next job—even forwarding external GC roles to his own lieutenants—creating transparency, reducing surprise attrition, and building a long-term reputation that attracts and boomerangs top talent.
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Create empathy and speed in executive decisions with clear structure.
In contentious trade-offs (profit vs. ...
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Dogfood with humility to sharpen customer obsession and filter hires.
DoorDash’s WeDash program, requiring employees (including execs) to deliver orders or do support, surfaces product bugs, builds real customer empathy, and self-selects for candidates willing to perform “unsexy” frontline work.
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In BD, validate with scrappy tests and build reusable platforms.
Rather than overinvesting in bespoke integrations (e. ...
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Notable Quotes
“If you're really a founder, you just have to find a way. You have to keep going. There's no question.”
— Keith Yandell (relaying Tony Xu’s view on founders)
“People talk a lot about hiring people better than you. People don’t talk a lot about what you do when you hire those people.”
— Keith Yandell
“I told him, ‘During the interview you kind of seemed like an asshole. Are you an asshole?’”
— Keith Yandell
“Doing the right thing is never the wrong thing.”
— Keith Yandell (quoting Ted Lasso while describing Tony Xu’s pandemic decision)
“For better and for worse, everything’s temporary. So the highs, you can’t get too high. The lows, you can’t get too low.”
— Keith Yandell
Questions Answered in This Episode
How could I create my own ‘How to Work with Me’ document to better onboard new teammates and set expectations?
Keith Yandell, longtime DoorDash executive and former Uber litigator, shares how empathy, humility, and founder-led urgency shape DoorDash’s culture and decision-making. ...
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What concrete steps can I take to build a true ‘no asshole, no politics’ culture in my team without it becoming empty rhetoric?
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In what areas of my company would a thoughtful generalist leader (backed by strong experts) outperform a deep specialist, and how might I experiment with that?
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How can I safely adopt Keith’s practice of helping reports explore external opportunities without undermining my own org in the short term?
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Where am I over-investing in bespoke product work for partnerships, and what quick, scrappy tests could I run first to validate real demand?
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Transcript Preview
Every business that you have heard of has gotten rejected by at least a handful of venture capitalists at one point or another. And so that drive to keep going if you believe in the business is critical, absolutely critical. I mean we- we were weeks of runway situation and had been told no by everyone, and it was just Tony's drive really to keep going. And the way he explains it to me is it's just the difference between a founder and a non-founder. Like if you're really a founder, you just have to find a way, you have to keep going, there's no question. And I mean, that- that's the only advice I can give folks is it only takes, only takes one yes, but you got to keep going.
(Instrumental music) Welcome to Lenny's Podcast where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. Today my guest is Keith Yandel. Keith is a longtime leader at DoorDash where he's been for about seven years, and in that time, get this, he's led the legal team, the HR team, the marketing team, the customer support team, and currently, he leads the BD and corporate development teams. Before DoorDash, he led litigation at Uber. He's also managed folks like Gokul Rajaram, who was previously on this podcast and who suggested that I have Keith on, and damn was he right. Before I had this chat with Keith, I didn't know that much about him, but now you can count me as a huge Keith fanboy. I suspect you'll feel the same way after you listen to this episode. I'm just gonna jump right in and bring you Keith Yandel after a short word from our wonderful sponsors. Today's episode is brought to you by OneSchema, the embeddable CSV importer for SaaS. Customers always seem to want to give you their data in the messiest possible CSV file and building a spreadsheet importer becomes a never-ending sink for your engineering and support resources. You keep adding features to your spreadsheet importer, but customers keep running into issues. Six months later you're fixing yet another date conversion edge case bug. Most tools aren't built for handling messy data, but OneSchema is. Companies like Scale AI and Pave are using OneSchema to make it fast and easy to launch delightful spreadsheet import experiences, from embeddable CSV import to importing CSVs from an SFTP folder on a recurring basis. Spreadsheet import is such an awful experience in so many products. Customers get frustrated by useless messages like error on line 53 and never end up getting started with your product. OneSchema intelligently corrects messy data so that your customers don't have to spend hours in Excel just to get started with your product. For listeners of this podcast, OneSchema is offering a $1,000 discount. Learn more at oneschema.co/Lenny. This episode is brought to you by Amplitude. If you're setting up your analytics stack but not using Amplitude, what are you doing? Anyone can sell you analytics while Amplitude unlocks the power of your product and guides you every step of the way. Get the right data, ask the right questions, get the right answers, and make growth happen. To get started with Amplitude for free visit amplitude.com. Amplitude, power to your products. Keith welcome to the podcast.
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