Episode summary
Why Leaders Should Rethink the Way They Handle Mistakes
Wall Street Week
· · Guests: Joshua Steiner, Michael Lynton
Summary
The conversation centers on the difference between mistakes and failures, and why that distinction matters for leaders. The host frames Joshua Steiner and Michael Lynton’s book, Mistakes to Meaning, as an effort to examine embarrassing errors that people usually avoid revisiting, rather than the more familiar business topics of success and failure. The two argue that mistakes are often made without full self-awareness, while failures are intentional efforts that do not work out.
Lynton revisits the decision to greenlight The Interview, saying the core mistake was agreeing to make the movie and letting the room’s enthusiasm override judgment. He describes the Sony cyberattack that followed as the consequence of that decision and says his instinct was to suppress the episode rather than reflect on it. Steiner tells a parallel story from his time as a young Treasury chief of staff, when a personal diary became public during the Whitewater investigation. Both say the book’s goal is not to eliminate mistakes, but to understand them, reduce shame, and make better decisions the next time.
Psychologist Allison Papadakis adds that people often overestimate how much others are focused on their errors, and that pausing before acting can help.
Key takeaways
- Lynton says the central Sony mistake was agreeing to make The Interview, not just enduring the later cyberattack.
- Steiner argues that a personal diary itself was not the mistake; writing sensitive Whitewater material in it was.
- The book’s thesis is that hiding a mistake creates a “whole new mistake” by adding shame and preventing learning.
- Papadakis says the “spotlight effect” makes people think others dwell on their mistakes far more than they actually do.
- The authors argue that a brief “cheetah pause” before acting can reduce emotionally driven errors.
Notable quotes
“Words matter and it's mistakes to meaning not failures to meaning. That's an important distinction”
“mistakes are something that you do without self-awareness, without understanding the context in which you're operating and that you end up regretting”
“At the core core, it was agreeing to make the movie The Interview”
“I really wanted to be on the other side of the table, so to speak, with the creative community”
“If the inclination of that loan officer and that investor is to hide that mistake, to not talk about the mistake, they're making a whole new mistake”
How the episode opens
We like to say that we can learn from our mistakes. But when it's a big, truly embarrassing mistake, we sometimes do everything we can not to revisit it. Now, two names well known to Wall Street have decided to write a book unpacking what went wrong for them and why.
for Michael Linton when he ran Sony Pictures and for Josh Steiner when he was chief of staff to the Treasury Secretary in the Clinton administration. Their book is from mistakes to meaning owning your past so it doesn't own you.
Words matter and it's mistakes to meaning not failures to meaning. That's an important distinction.
Yeah, it's a really important point for us. There have been great books written about success and about failure. And we think of success and failure as siblings.
You know, in both cases, you have a group of people. They come together. They're trying to do something meaningful.
They have a plan to do it. In one case, it turns out well. In the other case, it doesn't.
But they're both intentional. One way to think about it, at least the way we thought about it, was there's a reason we say marriages fail and that if you get married at 3:00 a.m. in Vegas after a couple of cocktails, that's a mistake.
In the case of marriage, people come together. They want to do something meaningful. It doesn't work out.
So, it failed. But mistakes are something that you do without self-awareness, without understanding the context in which you're operating and that you end up regretting.
And the other thing is that maybe with the exception of marriage, not that many people have the opportunity to have failures. You know, it does require a pretty substantial or significant decision to be made.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- leadership and mistakes
- organizational failure vs mistakes
- handling errors
- sony interview decision
- cyberattack consequences
Companies and tickers mentioned
- Sony
Watch the episode
Watch “Why Leaders Should Rethink the Way They Handle Mistakes” on YouTube
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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