Software Misadventures · Ronak Nathani, Guang Yang

Cory Watson - Leading observability teams at Twitter & Stripe, how to succeed in a new org, effective ways to advocate for your team and more - #16

·1 hr 24 min·5 clips

A dial-up support caller taught Corey Watson that anger never fixes a technical problem faster.

1. Software Misadventures presents Corey Watson’s career in customer support, observability, technical leadership, Twitter, and Stripe. 2. Ronak, Austin, and Guang host Watson, a Jelly.io solutions engineer whose stated career included Twitter, Stripe, and SignalFX observability work. 3. The conversation asks how patience, empathy, and practical advocacy help engineers lead teams through incidents and organizational change. 4. Watson began in the mid-1990s at an internet café and later a rural Middle Tennessee dial-up ISP. 5. The café had a T1 connection, while customers commonly used 28.8 or 33.6 kilobit-per-second dial-up. 6. Watson helped Windows 3.1 users install TCP/IP stacks, configure modem initialization strings, and connect to the internet. 7. A frustrated support caller told Watson, “you being mad at me ain’t gonna fix this any faster.” 8. Watson says that caller’s lesson influenced how he supported infrastructure teams, customers, vendors, and leadership. 9. He describes empathy as asking what another person is trying to accomplish and what motivates their request. 10. Watson contrasts an incident leader seeking a customer-facing restoration with an engineer responding to a file-handle alert. 11. Watson argues that senior engineers need an opinion about how systems ought to work, not only empathy for competing views. 12. He says engineers can make ten other people slightly better, rather than relying on the idea of isolated “10x engineers.” 13. Watson recalls joining Twitter as an early embedded SRE and encountering a physical data-center power outage during his first week. 14. He says restoring Twitter was difficult because systems restarted with cold caches and created a thundering-herd problem. 15. Watson also spilled coffee on Stefan’s desk and later broke Twitter’s observability read side with a dashboard named using emoji. 16. The dashboard included a spinning star, an alien, and the poop emoji, after which someone edited the database and emoji support was added. 17. Watson says his first attempt at managing Twitter’s observability team listed everything the group could do, unintentionally making the scope impossible to execute. 18. He now views CTO-level work as a role dominated by trade-offs, customer changes, and information asymmetry rather than simple technical control. 19. Observability engineers will value Watson’s incident and leadership stories. 20. Listeners seeking only product tutorials may skip this career interview.

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