The Ledger

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Insight
Sager: Most toxic high performers reform when given direct, constructive feedback
“Once you say that to people, the vast majority of people I've ever worked with, Their reaction to this is, hey, Eric, thank you. I really appreciate you caring about me enough to give me that feedback. And then they do their best to course correct. And it migh…”
Eric Sager Jul 16, 2026 ▶ 8:05 Why great leaders make themselves obsolete | Eric Sager (COO, Plaid)
Insight
Sager: The idea that faster execution is always better is nonsense
“I don't think it's fair to say that, Hey, no matter what the decision is or what you're talking about in the context of the business, that faster is always better. I think that's nonsense, right? And there's plenty of examples where you don't want to do that.”
Eric Sager Jul 16, 2026 ▶ 11:26 Why great leaders make themselves obsolete | Eric Sager (COO, Plaid)
Insight
Sager: The ultimate test of leadership is making yourself obsolete
“And in some ways, to me, that's like the ultimate asset test of, did you do a good job or not? And you know, my own lived experience is like, every time I've thought I've made myself useless and obsolete, like there's always been some new opportunity, right? T…”
Eric Sager Jul 16, 2026 ▶ 39:18 Why great leaders make themselves obsolete | Eric Sager (COO, Plaid)
Insight
Sager: Hiring solely for domain expertise fails as domain advantages erode in 18 months
“But I think if that's the main reason you hire someone. I think that oftentimes doesn't work out because you end up overlooking like all these other things that are far more important in terms of like what that person's ceiling is. You know, I was a consultant…”
Eric Sager Jul 16, 2026 ▶ 57:06 Why great leaders make themselves obsolete | Eric Sager (COO, Plaid)
Insight
Sager: Founders have a level of resilience no hire will ever match
“It gives you a level of resilience that nobody you ever hire is ever going to have.”
Eric Sager Jul 16, 2026 ▶ 1:00:34 Why great leaders make themselves obsolete | Eric Sager (COO, Plaid)
Insight
Sager: The only great startup outcomes are huge success or fast failure
“There's kind of two outcomes that are great. If you start a company, right? One is you retain control of it and it becomes huge. The second is it fails quickly.”
Eric Sager Jul 16, 2026 ▶ 1:01:18 Why great leaders make themselves obsolete | Eric Sager (COO, Plaid)
Insight
Sager: Platforms should prioritize network growth over short-term revenue
“So there's a bit of a bias there to say, not just what makes me the most money, but it's first and foremost about what's, what allows us to build the network. Because it's the network that then delivers a better outcome for consumers, it delivers out better ou…”
Eric Sager Jul 16, 2026 ▶ 28:37 Why great leaders make themselves obsolete | Eric Sager (COO, Plaid)
Insight
Sager: Candidates interviewing across disconnected hype sectors lack genuine product affinity
“Some simple things are just like, what other roles are you looking at? And like, why? Like what connects all of them? And I think if you get an answer to that, that's like, well, I'm looking at this company over here, like in AI, and then I'm looking at this o…”
Eric Sager Jul 16, 2026 ▶ 54:42 Why great leaders make themselves obsolete | Eric Sager (COO, Plaid)
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