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Keith Yandell (DoorDash, Uber)09 February 2023

Leading with empathy

10Frameworks
14Insights

Frameworks in this episode

Finance5 steps

Beat-Your-Plan Fundraising: Trade Dilution for Trust

Pitch numbers you'll hit, eat the lower valuation, and turn every passer into a future lead.

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Leadership5 steps

Career-First Management: Help Them Find Their Next Job

Commit to helping reports leave, and win transparency, backfill lead time, and reputation.

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Productivity4 steps

Compounding Urgency: Pull the Roadmap Up a Week

Ship a week earlier, start the next thing a week sooner, and the gap compounds into a lap.

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Communication6 steps

Demand-Feedback-First (T3/B3)

Force your team to critique you before you critique them — then report back what you changed.

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Strategy5 steps

The BD-Product Operating Contract

Test deals with hacky ops before code, build platforms not bespoke, time product's entry.

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Leadership6 steps

The Empathy Steel-Man Decision Framework

Make each side argue the other's case, then name the tiebreaker and the deadline before debating.

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Leadership5 steps

The Generalist Placement Play

Put a non-expert in charge to unlock 10x thinking, then hire the expert and get out of the way.

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Leadership5 steps

The 'How to Work With Me' Document

Scale culture through one written doc: expectations, your real flaws, your commitments.

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Leadership6 steps

The Post-Interview Culture Probe

Give a strong-but-culturally-questionable candidate blunt feedback and hire on how they react.

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Leadership5 steps

WeDash: Mandatory Dogfooding as a Culture Governor

Make every employee do frontline work, then advertise it in interviews to self-select hires.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 3

Hot Take14:00

Why Tony Puts Non-Experts in Charge of Teams

Keith led HR, marketing, support, legal and more at DoorDash despite lacking expertise in most. Tony gave him the book Range and argued that experts tend to do things the way they've always been done, so they deliver incremental gains; a generalist is more likely to reinvent the system for a 10x outcome. Keith's job then became hiring the real experts and getting out of their way.

  • Tony deliberately assigns roles to people who aren't subject-matter experts to avoid incremental thinking.
  • The thesis comes from David Epstein's book 'Range' — Nobel winners often excel outside their prize field.
  • Keith's approach: admit up front he doesn't know the field, hire the best expert, add what value he can, then get out of the way.
  • Experts were attracted to working for a leader honest about what he didn't know.

“if you want to achieve a 10x outcome hiring someone that's an expert in the field it's maybe unlikely you're going to achieve that 10x…”

Keith Yandell · 14:30

“I know you don't know how to do this stuff that's why I'm putting you in the role”

Keith Yandell · 15:00
#leadership#generalists#hiring#management
Hot Take22:00

Help the People You Manage Find Their Next Job — Even Elsewhere

Keith actively helps people he manages find their next role, even at other companies, and even forwarded external GC recruiter pitches to his report Tia. He argues it makes people more transparent about leaving, builds an unbeatable manager reputation via blind references, and pays back 10x over a long career horizon.

  • Openly offering to help people leave makes them transparent so you can plan backfills and avoid surprises.
  • Blind references then report that you put the individual first, which is deeply motivating to future hires.
  • He forwarded GC recruiter inbounds to Tia; she chose to stay and grew into general counsel.
  • You might lose one talented person, but they'd probably have left anyway — and the reputation compounds.

“what they're going to hear is Keith's gonna put you first and I think that's really motivating for a lot of people”

Keith Yandell · 23:00

“hey Tia I don't know when this job's going to be available here I'm still liking what I'm doing I think I'm still adding value…”

Keith Yandell · 25:00
#management#retention#leadership#career
Hot Take35:30

Tough Times Make Companies

Keith got board advice he initially disliked: tough times make companies. Downturns reveal who's a mercenary versus mission-driven, force discipline on unit economics, and flood the market with talent. He also found DoorDash employees actually like crises because they create singularity of focus and guaranteed resourcing on the one main thing.

  • Hard times reveal who's on the team for the mission versus a quick payday.
  • Constrained funding forced DoorDash to obsess over unit economics early — a lasting advantage.
  • Downturns are the best hiring markets; Keith cites a Bill Gurley-style 'best time since 2008 to start a company' sentiment.
  • Internal surveys showed people like crises for their singularity of focus and clear resourcing.

“tough times make companies for a host of reasons”

Keith Yandell · 35:30

“you're gonna find out who the mercenaries are on the team that are people that are there for the mission versus they're there because they…”

Keith Yandell · 35:30
#leadership#startups#crisis#hiring

Explainer· 3

Explainer08:30

WeDash: Why Every DoorDash Employee Delivers Food

DoorDash runs a program called WeDash where all employees must do deliveries at least four times a year (Keith does it monthly). It builds customer empathy, surfaces product bugs, and also acts as a hiring filter — signing up to deliver McDonald's takes a level of humility that screens for the people who thrive there.

  • All employees are required to dash at least four times a year; support work is an alternative for those who can't.
  • Keith once found a routing bug that used straight-line distance instead of roads, which then got fixed.
  • The program is flagged in interviews as an expectation, acting as a 'governor' that attracts humble, customer-obsessed people.
  • Airbnb tried a similar 'everyone be a host' program but found it much harder to operationalize.

“we have a program called we Dash where four times a year all employees are required to go do deliveries”

Keith Yandell · 08:30

“not every software engineer wants to hop in their Tesla and go out and deliver McDonald's to some kids”

Keith Yandell · 12:30
#culture#product#customer-obsession#hiring
Explainer38:00

The Compounding Power of Shipping One Week Sooner

Keith explains Tony's relentless urgency as compound interest applied to product: pushing a roadmap up even a week means you start the next thing a week sooner, lapping competitors who are one week behind. Small repeated gains (1.01x) grow over time, and the discipline is to resist self-congratulation and stay hungry.

  • Continuously shipping a week sooner compounds into lapping competitors over time.
  • Tony constantly asks whether a test is really needed or the team can ship now.
  • On IPO day there was no champagne — straight into the weekly business review with tough questions.
  • Staying hungry beats being self-congratulatory: someone out there is practicing to beat you.

“if you can continuously push up what you ship by a week you're going to end up lapping competitors who are just one week behind”

Keith Yandell · 38:30

“somewhere someone out there is practicing and when you meet them they will beat you”

Keith Yandell · 40:00
#product#urgency#execution#leadership
Explainer40:30

The Traits Keith Sees in Great Founders

Asked what separates real founders, Keith names a handful of recurring traits: obsessiveness, hyper-competitiveness, a knack for manufacturing straw men or motivation even when things are going well (like Michael Jordan inventing slights), and a raw curiosity about how things work. Together these create a drive that never turns off.

  • Common founder traits: obsessiveness and hyper-competitiveness.
  • Great founders manufacture 'straw men' for motivation — like Michael Jordan taking things out of context as bulletin-board material.
  • Raw curiosity about how things work is a third defining trait.
  • The combination produces a drive founders can't switch off, though it can be a lonely path.

“there's a handful of (41:00) traits I've seen that are pretty common one is a level of obsessiveness two is hyper competitiveness”

Keith Yandell · 41:00

“like Michael Jordan used to take things out of context and put make bullets and board material”

Keith Yandell · 41:00
#founders#leadership#psychology#drive

Story· 3

Story03:30

Calling a Candidate Out — and Why It Made Him Join

Keith left an interview convinced VP of Eng candidate Ryan Sokol was a jerk and told CEO Tony Xu not to hire him. Tony asked him to have dinner first, where Keith directly asked Ryan if he was an asshole. Ryan owned it, they became friends, and Ryan later said the willingness to hold a culture bar was exactly why he joined.

  • DoorDash prides itself on a 'no politics, no [__]' culture, so the culture read mattered as much as the skills.
  • Tony pushed back on the snap judgment and asked Keith to have dinner before deciding.
  • Ryan's non-defensive reaction — asking what he'd done and how to improve — flipped Keith's impression in two minutes.
  • Ryan joined partly because DoorDash was willing to pass on a super-qualified hire over attitude.

“I said Ryan during the interview you kind of seemed like an [ __ ] are you an [ __ ]”

Keith Yandell · 05:00

“his perspective is Life's too short to work with people you don't really enjoy”

Keith Yandell · 05:30
#hiring#culture#interviewing#feedback
Story09:00

Keith's 8-Year-Old Calls the CEO About a Broken Delivery

On a WeDash delivery with his eight-year-old daughter, Keith got an order requiring an 18.5-mile drive for a sandwich and coffee. His daughter insisted on calling CEO Tony Xu directly and laid into him about the bad experience. Rather than take offense, Tony called it insightful feedback and had emailed a fix to the product org before they got home.

  • The order made no sense for driver or customer — an 18.5-mile drive for a sandwich and coffee.
  • Tony treated blunt feedback from a child as one of the most insightful pieces he'd gotten recently.
  • He emailed the product organization with the problem and suggested fix before they'd even driven home.
  • Illustrates DoorDash's bias to action and Tony's habit of doing customer support daily.

“she just lays into him she said this is going to take us 36 minutes to drop off the coffee's not gonna be hot how…”

Keith Yandell · 09:30

“by the time we got home he'd actually sent an email out to the product organization calling out the problems suggesting the fix and they…”

Keith Yandell · 10:00
#customer-obsession#leadership#bias-to-action#culture
Story41:30

The Pandemic Rollercoaster and Cutting $100M in Commissions

Keith recounts COVID whiplash at DoorDash: volume cratered as lockdown hit, then doubled while global support centers shut and the app crashed every Friday night. In the middle of prepping to IPO, Tony overruled Keith's objection and cut roughly $100M in restaurant commissions as a founder-led decision, invoking that doing the right thing is never the wrong thing.

  • Volume dropped off a cliff at lockdown, then doubled just as support centers worldwide closed.
  • They weren't planning to grow that fast, so infrastructure buckled and the app crashed Friday nights.
  • Rising NPS showed the product became an essential service during the crisis.
  • Tony overruled Keith and cut ~$100M in commissions to keep restaurants alive, calling it founder-led and right.

“volume dropped off a cliff and I was like oh went from super high we're getting ready to IPO super low volume's going to zero…”

Keith Yandell · 42:00

“it reminded me of the Ted lasso quote which is doing the right thing is never the wrong thing”

Keith Yandell · 44:00
#covid#leadership#decision-making#doordash

Tool· 1

Tool18:30

The 'How to Work With Keith' Document

To scale culture in a fast-growing company, Keith wrote a document covering three things: the traits of successful people at DoorDash, his own areas for improvement and feedback he's received, and his commitments to his team. It set expectations, built trust with new hires, and helped a legendary CMO decide to join because of how transparent it was.

  • Written work product scales culture better than in-person osmosis in a hyper-growth company.
  • Three sections: success traits, his own weaknesses and feedback, and commitments to the team.
  • He shares that as a litigator he argues even when he agrees, to test conviction — and flags it as something he's working on.
  • Future CMO Kofi cited the doc's transparency as an important factor in joining.

“one thing that Tony taught me is one thing that scales really well is written work product”

Keith Yandell · 19:00

“so I'm committed to finding you your next job even if that's not at doordash Life's too short to be in a job you don't…”

Keith Yandell · 20:00
#management#culture#leadership#onboarding

Takeaway· 4

Takeaway06:00

Give Tough Feedback After an Interview to See How They Take It

Keith's lesson from the Ryan Sokol episode: if you liked a candidate but have a concern (especially on culture fit), give them the direct feedback and watch how they respond. A genuine jerk reacts badly; a strong hire engages with it, so the feedback itself becomes a test.

  • Direct post-interview feedback reveals how someone handles being challenged.
  • It doubles as a preview of how they'd interact with you day to day.
  • Best used when you otherwise liked the person but have a single area of concern.

“when you're interviewing someone giving them tough feedback after the interview if there's an area of concern but you otherwise liked them can be a…”

Keith Yandell · 06:00
#hiring#feedback#interviewing
Takeaway31:30

Demand Feedback First — the T3 B3 System

Keith reserves time in 1:1s to require constructive feedback for himself before giving any, which makes two-way feedback easier since new managers often avoid criticism. He learned this from Travis at Uber via 'T3 B3' — three positives and three constructive pieces for your manager — enforced so directly the CEO would call you out for going soft.

  • Creating a space that requires constructive feedback makes it easier for everyone to give it.
  • Keith presses reports if they won't offer constructive feedback in a 1:1.
  • T3 B3 (from Uber): three top positives and three constructive criticisms of your manager each review.
  • Enforcement mattered — Travis personally called it 'totally unacceptable' when Keith only gave praise.

“if you create a space where you require constructive feedback it's a lot easier to give feedback”

Keith Yandell · 31:30

“we had a system called T3 B3 where during reviews or or pulse check-ins you'd have to say three positives about your manager and three…”

Keith Yandell · 32:00
#feedback#management#1-on-1s#culture
Takeaway45:30

Put Up Numbers You'll Actually Hit, Not Stretch Plans

Keith says nearly every DoorDash round ended up led by an investor who'd passed in a prior round, because the company consistently hit the numbers it promised. Most companies show stretch plans they miss; DoorDash deliberately put forward conservative numbers, trading some early dilution for a durable base of investor trust.

  • Almost every round was led by a firm that had previously said no — after DoorDash proved it hits its numbers.
  • Most founders put up stretch plans; DoorDash refused, which cost some dilution via lower valuations.
  • The payoff is investor conviction that the company will deliver what it says.
  • On raising in a downturn: it only takes one yes, so keep going.

“most people put up stretch plans but they don't but that was just not in our DNA we wanted to make sure that we we…”

Keith Yandell · 46:00

“there's a trust that builds from that where when we tell people we're going to do something that they have conviction that we're going to…”

Keith Yandell · 46:30
#fundraising#trust#founders#investors
Takeaway48:30

Making BD and Product Work: Platforms and Cheap Tests

Keith shares hard-won lessons on the BD–product relationship: bring product in at the right cadence (too early wastes precious engineering, too late gives away terms), build reusable platforms instead of bespoke integrations per deal, and test a deal thesis with hacky operations before spending product resources — a lesson from a failed franchised-hotel room-service integration.

  • Engineering is DoorDash's most precious resource — give BD pipeline visibility rather than pulling product into every early deal.
  • Rajat's lesson: build a scalable platform once so BD can negotiate within known parameters without new builds each time.
  • 'Dream big, start small' — test with hacky ops before committing product work.
  • A hotel room-service integration flopped because the chain was franchised; a one-hotel promo-code test would have exposed that first.

“why don't you figure out what the scalable solution is for this we will build you a product you won't need to come ask us…”

Keith Yandell · 49:30

“definitely building platforms dream big start small use operations to test a thesis around a deal before you actually expend the product resources”

Keith Yandell · 51:30
#business-development#product#partnerships#platforms