executive

also referred to as: executives

17 statements across 6 episodes · 11 bullish · 2 bearish · 6 people on the record · first statement Nov 16, 2023 by Will Larson · across every show →

Everything said about executive, oldest first

Nov 16, 2023 positive
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.”
Will Larson Nov 16, 2023 ▶ 1:06:07 A masterclass in engineering leadership from Carta, Stripe, and Uber | Will Larson (CTO at Carta)
Nov 16, 2023 positive
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.”
Will Larson Nov 16, 2023 ▶ 1:01:31 A masterclass in engineering leadership from Carta, Stripe, and Uber | Will Larson (CTO at Carta)
Nov 16, 2023
Insight
Larson: Engineering executives must educate peers instead of shielding teams
“The most valuable thing as an executive you can do is educate like the other execs on how engineering works, not kind of protecting engineering from visibility from anyone else.”
Will Larson Nov 16, 2023 ▶ 35:16 A masterclass in engineering leadership from Carta, Stripe, and Uber | Will Larson (CTO at Carta)
Nov 16, 2023 positive
Insight
Larson: Ask questions to extract insight from bad executive suggestions
“So like almost always when you get these like really like offhand random ideas from executives, there's a kernel of insight there that you can extract by kind of asking more, more detailed questions to them.”
Will Larson Nov 16, 2023 ▶ 59:10 A masterclass in engineering leadership from Carta, Stripe, and Uber | Will Larson (CTO at Carta)
Nov 16, 2023 neutral
Insight
Adapting to company context predicts if an executive lasts over a year
“And this is like one of the, to me, most predictive traits for whether an executive will last more than a year at a company. It's where they come in and they start with, Hey, can I, how can I change myself to fit versus how can I force my entire organization t…”
Will Larson Nov 16, 2023 ▶ 45:24 A masterclass in engineering leadership from Carta, Stripe, and Uber | Will Larson (CTO at Carta)
Nov 16, 2023 positive
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.”
Will Larson Nov 16, 2023 ▶ 1:03:10 A masterclass in engineering leadership from Carta, Stripe, and Uber | Will Larson (CTO at Carta)
Nov 16, 2023 positive
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.”
Will Larson Nov 16, 2023 ▶ 58:23 A masterclass in engineering leadership from Carta, Stripe, and Uber | Will Larson (CTO at Carta)
Apr 25, 2024 positive
Insight
MacInnis: Elite founders are energized by work but tortured by fear of failure
“I think they're fucking filled with happiness and enjoyment and energy and also tortured by the fear of failure and by whatever demons drive them or whatever passion drives them. Like there's this awesome Jekyll and Hyde yin yang You know, dynamic to what it's…”
Matt MacInnis Apr 25, 2024 ▶ 42:27 How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)
Mar 6, 2025 positive
Insight
De Milliano: Executives with firing experience execute necessary terminations faster
“Per your point, if the, if you just have to assume that the distribution of failures is, like, pretty much the same across the org, I think it's always a pretty good sign if people have fired a lot. It's only because, like, they're gonna have to in whatever jo…”
Eeke de Milliano Mar 6, 2025 ▶ 46:57 What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Stripe)
Mar 6, 2025 negative
Insight
de Milliano: Executives from only one prior company risk copy-pasting playbooks
“But a leader who's only been at one other company, I think I'd always have a few questions about because they're going to be very tempted to copy paste everything that they did.”
Eeke de Milliano Mar 6, 2025 ▶ 43:02 What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Stripe)
Mar 6, 2025 negative
Insight
de Milliano: Multiple consecutive two-year stints signal mercenary executive behavior
“I personally really worry about the, like, the two-year stints, sort of, like, multiple, like, two-year stints. Like, it just actually isn't enough time to show that you've done anything significant, I think, as a leader. So, like, this is a gross generalizati…”
Eeke de Milliano Mar 6, 2025 ▶ 42:21 What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Stripe)
Mar 6, 2025 positive
Insight
De Milliano: Former colleagues following an executive is a strong hiring signal
“How many people moved to the next company that you worked at, that you worked with before? I think it's always a really, really good sign.”
Eeke de Milliano Mar 6, 2025 ▶ 46:45 What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Stripe)
Mar 6, 2025 neutral
Insight
de Milliano: Executive candidates succeeded elsewhere; the challenge is fit
“Like the funny thing about all these things, like when you are interviewing someone, inevitably they were good for someone somewhere. Otherwise you probably wouldn't be interviewing them, but it's the hard part is finding the right fit.”
Eeke de Milliano Mar 6, 2025 ▶ 4:51 What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Stripe)
May 22, 2025 positive
Insight
Kao: Frame recommendations under a founder's existing values, not new ones
“It is much better To frame whatever it is you want to talk to them about or your recommendation under an existing umbrella of what they already care about, of values they already have, of ways that they already think the business should be run.”
Wes Kao May 22, 2025 ▶ 18:34 How Wes Kao coaches founders to influence, lead, and get what they want | (Co-founder of Maven)
May 22, 2025 positive
Insight
Kao: Executives succeed when treating a founder's personality as a constraint
“I think that many pairings of execs and founders that work really well are when execs recognize that their founder can be spiky in different ways that might not really make sense, that they are really good at certain things and not as good as at other things. …”
Wes Kao May 22, 2025 ▶ 19:44 How Wes Kao coaches founders to influence, lead, and get what they want | (Co-founder of Maven)
Mar 26, 2026
Insight
Kreps: CEOs must learn ~80% of what functional executives know
“I think CEOs need to know, you know, about 80% of what their executives know about their function, I think, over time. So really kind of learn that discipline. Not enough to be good Add it, but enough to be, to know what good is and know if it's going well.”
Jay Kreps Mar 26, 2026 ▶ 3:31 How to build a company when you’re not an optimist | Jay Kreps (Co-founder and CEO, Confluent)
Jul 16, 2026 positive
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)
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