Leading with empathy | Keith Yandell (DoorDash, Uber) | Free Podcast Summary

Keith Yandell started at DoorDash as Chief Legal Officer, and during his tenure, he has also led the HR, Customer Support, Marketing, and now Corporate Development teams.

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.

I believe in hiring the best experts and then getting out of their way.

I think it’s important to help employees find new opportunities, even if it means they leave the company.

Persistence in the face of rejection is crucial for success in business. Creating a positive workplace culture with no politics and no assholes fosters collaboration and success.

To scale a company, it’s important to hire talented people and let them work without micromanagement. Creating a culture of collaboration and outlining company values can lead to a successful and efficient team.

To retain top talent, executives should be transparent with their employees from the beginning. Share a document that outlines areas for growth and how you plan to be helpful. Offer to help team members find their next job, creating a better reputation for managers and the company.

Career development conversations in one-on-one meetings and investing in employee success can foster loyalty and motivation. Strong leadership includes recognizing individual motivations and experiences while unifying a team.

When making big decisions, I try to bring everyone to the table and find a solution that works for all teams involved.

Understand both sides of an argument, ask each side to make the opposite case, clarify the decision maker and time horizon, and include space for feedback for a more positive and productive work environment.

Providing open communication with constructive feedback and taking action on it can create a safe environment for tough conversations, motivate team members, and build a healthy team culture. In tough times, identify who is there for the mission versus quick riches.

Tough times can lead to long-term success for startups through discipline and focus on unit economics, the opportunity to find talented people, and a singularity of focus and urgency. Founders must continuously push for progress and stay ahead of the competition.

Successful founders maintain a level of obsessiveness, competitiveness, and curiosity.

Founders should trust their instincts, have faith, persist through rejection to succeed in fundraising, and focus on finding opportunities to help their business reach its potential, even during challenging times.

Timing is crucial for a successful partnership between BD and product teams; involve the product team at the right time, give them visibility into the pipeline, test new ideas through operations, and embrace the concept of “Dream big, start small”.