Leading with empathy | Keith Yandell (DoorDash, Uber)

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Keith Yandell started at DoorDash as Chief Legal Officer and during his tenure has also led the HR, Customer Support, Marketing, and now Corporate Development teams. In today’s episode, we talk about leadership, and how to lead with empathy. We dig into DoorDash’s unique culture and touch on the WeDash program, which requires every employee to complete four deliveries a year in order to better understand the customer experience. Keith shares his “How to Work with Keith” document and discusses the importance of openness in the workplace. He also gives some tips for founders on hiring, engaging with legal, and how to make big decisions when teams are competing for resources.

Listen now on Apple, Spotify, Google, Overcast, and YouTube.

Find the transcript for this episode and all past episodes at: https://www.lennyspodcast.com/episodes/. Today’s transcript will be live by 8 a.m. PT.

Where to find Keith Yandell:

• Twitter: https://twitter.com/kdyandell

• LinkedIn: https://www.linkedin.com/in/keith-yandell-2a947432/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• Twitter: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

Referenced:

• Gokul Rajaram on Lenny’s Podcast: https://www.lennyspodcast.com/gokul-rajaram-on-designing-your-product-development-process-when-and-how-to-hire-your-first-pm-a-playbook-for-hiring-leaders-getting-ahead-in-you-career-how-to-get-started-angel-investing-more/

• Ryan Sokol on LinkedIn: https://www.linkedin.com/in/ryan-sokol-00b2333/

• Tony Xu on LinkedIn: https://www.linkedin.com/in/xutony/

• About WeDash: https://doordash.news/culture/wedash-doordash-employee-program-how-does-it-work/

•  Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484

• Kofi Amoo-Gottfried on LinkedIn: https://www.linkedin.com/in/kofi-amoo-gottfried-3802bb3/

• Tia Sherringham on LinkedIn: https://www.linkedin.com/in/tiasherringham/

• Amp It Up: Leading for Hypergrowth by Raising Expectations, Increasing Urgency, and Elevating Intensity: https://www.amazon.com/Amp-Unlocking-Hypergrowth-Expectations-Intensity/dp/1119836115

• Ted Lasso’s quote on Twitter: https://twitter.com/TedLasso/status/1426932132417576967

• Rajat Shroff on LinkedIn: https://www.linkedin.com/in/rajatshroff/

• Micah Moreau on LinkedIn: https://www.linkedin.com/in/micahmoreau/

In this episode, we cover:

(00:00) Keith’s background

(03:41) The time Keith asked a potential hire if he was an asshole

(06:39) DoorDash culture

(08:40) The WeDash program

(13:16) How Keith was able to lead so many different teams at DoorDash

(16:08) Hiring the best experts and then getting out of their way

(18:21) The “How to Work with Keith” document

(21:52) How and why Keith helps his employees land new jobs

(27:22) How he leverages empathy to unify board members

(29:26) The importance of assigning a decision maker and a time horizon for the decision

(31:15) One-on-ones with Keith, and the T3 B3 framework from Uber

(33:12) How to encourage constructive criticism from employees

(34:49) What it’s like to lead in tough times and why it can actually make your org stronger

(37:42) How creating urgency compounds gains

(39:11) IPO day at DoorDash

(40:20) The characteristics of top founders

(41:33) How the pandemic impacted DoorDash

(44:40) Advice for new parents that is applicable in business 

(45:24) The difficulty of gaining funding

(46:58) Advice for founders struggling with fundraising

(48:02) How Keith developed a strong relationship with the VP of Product and Design

(50:27) Building an effective BD team within a product company

(52:36) How to engage with legal teams

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