Greylock executive in residence (EIR) Wade Chambers and partner Josh McFarland on cultivating and coaching engineering leaders.

In the latest Greymatter episode, we welcome back Twitter’s former head of revenue engineering, now Greylock executive in residence, Wade Chambers. He sits down with Greylock partner Josh McFarland to discuss what characteristics make a great engineering leader and the best environment to foster leadership.

Wade helped scale product and build out the engineering, product, and services team for TellApart (which Twitter acquired in 2015) at a time when the company was on track to almost triple its revenue to over $50 million. He and Josh, who cofounded TellApart and served as its CEO, share lessons learned from building their company, how founders can create a culture built on honest conversations, and advice for coaching up great engineering leaders.

Below are several key takeaways from the podcast. To hear more from Wade, listen to his previous Greymatter podcasts on Increasing Your Team’s Capacity to Win and the follow-up discussion on The Art of Hiring 10x Engineers.

  • Characteristics of a great engineering leader: Applying judgment is a required discipline to develop early on. This discipline is the transition from taking instruction to understanding the larger impact projects have on the company mission. One of the skills needed to reach this understanding is critical reasoning. (…)
  • Lead through change: Executive leadership must set up a culture to have honest conversations that creates an environment to allow others to make decisions. A key part of business is having to directionally make calls without precise data. It’s important to help guide teams to the right answer, create clarity about what’s important to the company, and constantly focus on building your organization to be nimble and invite change. (…)
  • Practice “radical candor”: “Care personally and deeply, but challenge directly.” Radical candor is needed when coaching engineering leaders. Work with each team member and create clarity about what their strengths and weaknesses are, where they want to be, and how you will coach them to reach their goals. (…)

Elisa Schreiber is the marketing partner at Greylock Partners.