Difficult Conversations

topic on 5 shows · 8 statements across 4 episodes · said 2 times in 2 episodes since 2020

Capital Allocators 1 20VC 1 More or Less the Knowledge Project BigDeal

Mentions by year, every show

tap a year for its mentions
0011112020202120222023episodesmentions
0112020202120222023episodes it came up in
000.50.5112020202120222023episodesmentions per episode

20VC 1Capital Allocators 1

every mention on every show, scene by scene, with the transcript →

8 statements about Difficult Conversations, every show

BIGDEAL Insight
Sanchez: A person's net worth scales with their difficult conversations
“The more difficult conversations you have, The higher the bank account you will eventually have.”
Codie Sanchez Nov 3, 2025 ▶ 13:46 Nothing and Nobody Will Ever Hurt You Again - After This.
20VC Insight
Mario Schlosser: Famous leaders are not better at having difficult conversations
“If you think that the people who are famous in this world somehow are good at these things, it's a complete nonsensical thing. In fact, one of the, I think they're good at They're better at avoiding these conversations than we are. You and I are good at maybe …”
Mario Schlosser Apr 5, 2024 ▶ 46:34 Mario Schlosser: "How to Deal with a 94% Decline in Market Cap" | E1136 · 20VC with Harry Stebbings
MORE OR LESS Prediction Not checkable as stated
Lessin: AI tools for rehearsing difficult conversations will be a massive space
“Like, if you told me that, like, the future is, like, there's, you know, you do use this stuff to be, like, I'm gonna fire someone. It's, like, here's what I'm gonna say. And you're like, all right, game, what are they gonna say back? And you, like, game theor…”
Sam Lessin Dec 1, 2023 ▶ 29:39 #25: TikTok, Porn and The Immediate Risks of AI · More or Less Podcast
Heen: Voicing More Feelings in Difficult Conversations Lowers the Stakes
“So actually, interestingly, someone is putting more feelings into the conversation. Lowers the stakes.”
Sheila Heen May 15, 2019 ▶ 57:34 #57 Sheila Heen: Decoding Difficult Conversations
Heen: Difficult conversations are driven by perceived threats to personal identity
“If a conversation feels difficult, there's often something about identity, something the situation suggests about you that raises the stakes on the whole conversation. And so that's part of the anxiety that then drives the intensity of the feelings.”
Sheila Heen May 15, 2019 ▶ 1:03:12 #57 Sheila Heen: Decoding Difficult Conversations
Heen: The identity traits people value most dictate their hardest conversations
“Whatever those sort of characteristics that you hold most tightly are, they are sometimes also a key to the kinds of conversations that are hardest for you. Because you let yourself down and you're disappointed in yourself.”
Sheila Heen May 15, 2019 ▶ 1:09:32 #57 Sheila Heen: Decoding Difficult Conversations
Heen: Difficult conversations are more fruitful when aimed at understanding, not persuasion
“If I shift my purpose in the conversation from getting them to change, or getting them to apologize, see that I'm right, whatever, to Just understanding better what's going on. Like, why is it that we have such a hard time with this? That conversation is much …”
Sheila Heen May 15, 2019 ▶ 1:25:36 #57 Sheila Heen: Decoding Difficult Conversations
Heen: Failure in difficult conversations means learning nothing, not lacking a solution
“Because not figuring out a solution isn't failing. Failing is not learning anything new about the other person.”
Sheila Heen May 15, 2019 ▶ 1:26:19 #57 Sheila Heen: Decoding Difficult Conversations

← every entity, every show

Made with StarZero

Turn any episode into a week of clips.

This entire site, thousands of episodes across every show transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.