Insight
Larson: CTO struggles usually stem from peer friction or poor shipping velocity
“Typically when a CEO of a 500 person company feels their CTO is, is struggling, they're probably running into like one of two different things. Either the individual CTO is like causing friction with other people on the team. For some reason, like their peers,…”
Insight
Larson: CEOs need a conviction view, not consensus, on executive performance
“Anything else is going to get like a kind of consensus view, but like you don't need a consensus view on executive performance. You as a CEO need to have like a conviction view on like whether it's actually good or not.”
Disclosure
Larson stopped shielding engineering teams and now exposes them to messy reality
“I used to be a big believer in the umbrella concept where it's okay, we should protect our team from the reality and problems around them so that they can focus. But as you work with more senior teams but also even as you just work in generally, I've come to b…”
Insight
Start executive presentations with conclusions and stop talking if they agree
“But when you present to execs, you should start with the conclusion. And then, if they already agree with you, stop presenting. Like, there's no reason to keep presenting.”
Insight
Larson: High-quality executive meetings require letting executives set the pace
“If you want, like, a high-quality exec meeting, you have to let the execs own the pace.”
Insight
Larson: Important disagreements with shared context must be debated live, not asynchronously
“Talking things through live when people do have the shared like context, they just disagree is incredibly valuable and it's almost impossible to kind of like get to the end of these things on like a chat on Slack or something. You really do have to like talk i…”
Assertion Not checkable as stated
Tech executives are struggling to find jobs after a year of searching
“And even in executive roles, I think there are people in there who are not getting traction after almost a year of searching, despite having many senior roles before.”
Assertion Supported
Stripe's core undocumented technical strategy was maintaining a Ruby monolith
“Undocumented strategies at Stripe was we use a Ruby monolith. And so everything was done in the Ruby programming language with a few minor exceptions.”
Disclosure
Stripe offered enterprise SLAs with financial penalties below four nines uptime
“So at Stripe, we had a reliability like SLA that we kind of extended to enterprise customers in terms of there was actually like a financial consequence to us if we dipped Below a certain level of uptime. Like I think it was less than four nines of API availab…”
Insight
Executive presentations must zoom from high-level goals to specifics in 30 seconds
“I think that the best folks presenting to executives start super zoomed out and then zoom in to their specific problem over the course of like 30 seconds.”
Insight
Larson: Calibrate executive presentations by pre-testing with chiefs of staff or EAs
“Testing a little bit with Folks who have context that aren't the exec themselves is the easiest way to help calibrate.”
Insight
The tech industry gives opportunities to learn rather than teaching proper execution
“Like we kind of joked earlier, like this isn't an industry that teaches you how to do things. It's an industry that gives you opportunities to learn how to do things.”
Will Larson