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The Debrief is a series of conversations with founders, executives, talent thought leaders on how they build talented and diverse teams, hosted by our own Teddy Chestnut. 

This week, Dick Costolo, investor and former CEO of Twitter joined The Debrief. He shared his expertise on building and scaling companies from the ground up. Some thought-provoking highlights from the conversation are below. 

Building teams from scratch (12:09) In the beginning you need generalists because people need to be able to do everything. “Draft the best available athlete” and find the right spot for them. Bring in specialists later.

How to hire for new roles (17:09) Seek outside expertise in the interview process to help vet candidates for expertise you don’t have. 

On management and empowering your team (29:35) Push decisions down the stack and let people own their decisions. Ownership is authority plus accountability.

Hiring for experience (41:55) Job descriptions are guidelines not dogma. Experience is sometimes just the illusion of competence. 

Managing to outcomes, not processes (43:48) You manage to outcomes with ownership and operating structure, not micromanaging process. Put people in charge, let them find solutions and hold them accountable for their solutions. Never punish people for making mistakes. It’s the job of leadership to correct mistakes when they happen, not prevent them from happening. 

How to be successful (53:54) There’s lots of different ways to be successful. From an investor perspective, you see lots of different personality types and characteristics that work, and the key is helping leaders understand what types of people they need to surround themselves with to be successful. 

Watch the full conversation below.

Tune in to our next episode of The Debrief with Kara Goldin, Founder and CEO of Hint, Inc on July 14th.

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