leader

also referred to as: leaders

10 statements across 9 episodes · 2 bullish · 2 bearish · 9 people on the record · first statement Feb 2, 2023 by Eeke de Milliano · across every show →

Everything said about leader, oldest first

Feb 2, 2023 negative
Insight
Milliano: Leaders want innovation's upside without accepting necessary failures
“Leaders want the upside of innovation, but they're not really willing to deal with the cost of innovation, which is like, look, if you're going to swing big, you will invariably stumble sometimes.”
Eeke de Milliano Feb 2, 2023 ▶ 22:17 How to foster innovation and big thinking | Eeke de Milliano (Retool, Stripe)
Jun 11, 2023 positive
Insight
Singhal: Leaders must not dismiss feedback criticizing their core strengths
“What you do need is to listen to contradictory feedback. So what was the premise here is you're being told that something that you hold as your strength is actually in your way or a development area. Do not dismiss that. Recognize most likely you're doing it c…”
Nikhyl Singhal Jun 11, 2023 ▶ 57:30 Building a long and meaningful career | Nikhyl Singhal (Meta, Google)
Nov 12, 2023
Insight
Chesky: Leaders cannot evaluate performance without being in the details
“I think there's a difference between micromanagement, which is like telling people exactly what to do and being in the details, being the details is what every responsible company's board does to the CEO. It doesn't mean the board is telling them what to do, b…”
Brian Chesky Nov 12, 2023 ▶ 32:26 Brian Chesky’s new playbook
Dec 21, 2023 neutral
Insight
Idiodi: Leaders fail at coaching because they never experienced it themselves
“The number one reason most people don't give good coaching is because they've never experienced good coaching themselves. And most people can only give to other people what has been given to them.”
Christian Idiodi Dec 21, 2023 ▶ 51:17 The essence of product management | Christian Idiodi (SVPG)
Apr 25, 2024 negative
Opinion
Robin: Employees abandon emotionless, robotic leaders once alternatives exist
“They're going to follow you for a while because you've got a really great idea, and the minute they've got another choice, man, they are out of there.”
Carole Robin Apr 25, 2024 ▶ 26:40 How to build deeper, more robust relationships | Carole Robin (Stanford professor, “Touchy Feely”)
Nov 23, 2025
Insight
Lockett: Always advising teams trains them to bring leaders every problem
“Great leaders know that when you try to advise and have the answer all the time, you're not actually equipping your team to go solve the hard problems. You're training your team to come to you with all of the hard problems. And coaching is a different way. It'…”
Rachel Lockett Nov 23, 2025 ▶ 10:12 A guide to difficult conversations, building high-trust teams, and designing a life you love
Nov 23, 2025
Insight
Lockett: Leaders should advise instead of coach when they want a specific outcome
“So don't coach and make it a game. Like, you want your person on your team to guess what's in your mind. That's a, not a good time to coach. You have something you absolutely want them to do. You know the right answer. You want them to be motivated to go do it…”
Rachel Lockett Nov 23, 2025 ▶ 12:50 A guide to difficult conversations, building high-trust teams, and designing a life you love
Jan 4, 2026 positive
Insight
Graham: Leaders must repeat roles and expectations dozens of times
“Re-clarifying roles and expectations, re-describing the elephant over and over and over again is one of the hardest parts about being a leader because you feel like a broken record, right? You feel like an idiot. You're like, I've said this 45 times. Turns out…”
Molly Graham Jan 4, 2026 ▶ 45:21 “I like being scared”: Molly Graham’s frameworks for rapid career growth | Molly Graham
Feb 1, 2026
Insight
Kennedy: Naming managerial intentions up front prevents perceived micromanagement
“When you name the intention very, very clearly for someone, they're much more likely to interpret your behavior through the intention you just named, because your intention isn't to control them or make them feel small. But if that's also something they have a…”
Dr. Becky Kennedy Feb 1, 2026 ▶ 34:55 A child psychologist’s guide to working with difficult adults | Dr. Becky Kennedy
Mar 22, 2026 neutral
Insight
Rachitsky: It is a product manager's fault if leadership rejects ideas
“The other thing I always tell people I've managed is it's your fault if the leaders didn't buy into your idea. Like it's not, you can't just be like, ah, they never, they just don't see it. It's not my fault. They agreed to do something else. I always tell the…”
Lenny Rachitsky Mar 22, 2026 ▶ 10:23 The art of influence: The single most important skill left that AI can’t replace | Jessica Fain
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