“The whole problem with the world is that fools and fanatics are always so certain of themselves, and wiser people so full of doubts.” -Bertrand Russell
It looks so easy, doesn’t it?
Oh, I suppose that “it” could be many things.
But for our purposes, I’m talking about someone with a leadership role in the Jewish Community whose performance you judge from the sidelines.
Admit it: We all do it.
Maybe it’s a rabbi, head of school, camp director, board chair, CEO, the Prime Minister of Israel, etc. Doesn’t matter. If you take a moment to visualize what they are currently doing in their role versus what you think they should be doing, it’s easy to imagine all the ways that you would do better were you in their chair.
But by now, you are aware that you over-estimate your abilities.
So do I. And so do all of us.
However, the story is more interesting than that.
People correctly guess they can complete all kinds of tasks; if we were always wrong, we would eventually stop guessing altogether. Returning to our temptation to judge from the sidelines, we sometimes make correct judgments about someone else’s poor performance.
As a result, understanding the difference between when we are right about our abilities and when we are wrong requires closer scrutiny.
And that brings us to this week’s big idea.
Hard-Easy Effect
As an homage to Bayesian Reasoning,1 pretend that I gave you a list of questions you need to answer, and when you answer, you need to both provide your prediction and guess the probability that you are right from 50-100. Some questions might include:
Who will win the Super Bowl in 2026?
Will it rain in the next hour?
Who was born first: George Washington or Abraham Lincoln?
Which “Jewish” food is better: the latke or the hamantaschen?
Who will win the presidential election in 2028?
Was Alexander Hamilton born Jewish? Yes or no?2
What year was the bombing of Pearl Harbor?
x3+y3+z3=k. Solve for x, y, and z.3
Some of these questions have a single right answer we can know now; others have a correct answer we can only learn in the future, and some ask a question implying that one should choose between two options, even though the question is much more complicated.
In 1977, Sarah Lichtenstein and our friend Baruch Fishhoff ran a series of experiments to gauge how well people calibrate the likelihood that they would answer certain questions correctly, such as identifying the ethnic origin of an artist by viewing a single painting or predicting the future trendlines in the stock market.4 By now, you can guess what happens: People get most answers wrong and overestimate the likelihood that their answer is right.
However, in another experiment, where participants were given a quiz of general knowledge questions, people overestimated the likelihood they would answer hard questions correctly and underestimated that they would answer easy questions correctly.5 These findings eventually become known as the “hard-easy effect” (HEE), which the Oxford Dictionary of Psychology defines as, “A tendency to be overconfident about the correctness of answers to difficult questions and underconfident about answers to easy questions.”
HEE is powerful because it demonstrates that we make systematic mistakes in calibrating our confidence level in the difficulty of completing a task. I had a hard time thinking of a practical example of this applies to the Jewish community, so here goes nothing (and feel free to tell me if this answer doesn’t convince you):
Scenario 1: Jeff has been a major critic of the CEO of a Jewish organization, writing editorials criticizing the organization’s lack of vision and serving as a resident gadfly on various committees, yelling about how “obvious” it is that the organization should be doing X instead of Y. After years of peripheral involvement, a new board chair appoints Jeff as the CEO. Upon learning what the CEO does all day, Jeff quickly proves incapable of doing the job. The organization’s health plummets.
Scenario 2: Jessica just completed her tenure as the CEO of a Jewish organization; her tenure had some successes and some failures, but overall, she was well-received. However, Sarah’s successor has a much tougher time in the role, and many criticize the successor from without and within. Key stakeholders approach Sarah to get validation for their complaints, and Sarah says, “Folks, it’s much harder than it looks.” Because Sarah remembers all the factors that go into a successful tenure, she discounts her opinion and chooses not to offer it.
In the former case, there is an entire range of things that the overconfident and inexperienced person never sees, thus leading them to simplistic explanations of why things are not working.
(By the way, this may also be why, on the rare occasion when the loudest complainer gets their shot to be in charge, they often fail so badly.)
In the latter case, the person who held the role before understands information others don’t and doesn’t make that mistake. Once a person develops a degree of expertise by seeing the same role from the inside, he/she/they know just how many factors affect whether or not one will be successful. As a result, while the experienced person may have a high degree of knowledge about certain basic elements of the job, their past with the job makes them reluctant to judge decisions without sufficient information.
While the hard-easy effect demonstrates how easily an overconfident will predict future success without justification, many of those tendencies will also apply when interpreting failure. And that brings us to this week’s book recommendation.
The Right Kind of Wrong
Amy Edmondson is back!6
We met Edmondson last May around Shavuot, so if you’ve forgotten her, read this article. But Edmondson is an organizational scientist credited with bringing the term “psychological safety” into the center of many leadership conversations. As a quick refresher,
In Teaming, Edmondson’s research on high-performing hospital teams demonstrates that the most successful teams report more mistakes because they combine high accountability and psychological safety.
In her new book, The Right Kind of Wrong: The Science of Failing Well, Edmondson tells the story of how she discovered this groundbreaking finding through a process of exploration that started with a perceived “failure,” the kind of failure we want to encounter on the road to success.
When Edmondson started her research into the science of teams, she assumed (reasonably) that higher-performing teams make fewer mistakes than lower-performing teams. When she first saw her data point in the other direction, she was freaked. Only when she reframed this “failure” did she eventually start on the path that led to “an intelligent failure that would lead to an unexpected discovery,”7 the one that made her famous in the world of leadership development.
The Right Kind of Wrong is a dive into the world of failure, detailing the nuances between the “good” failure Edmondson experienced and the kinds of failures all of us wish to avoid (and for good reason.) Edmondson’s schematic includes three types of failure:
Intelligent: The “best” kind of failure includes an unexpected discovery or problem that ultimately leads to an even more impactful discovery, like the famous story of how a scientist at 3M accidentally discovered what eventually became post-it notes.8
Basic: The most avoidable kind of failure, a basic failure, can mostly be avoided through better procedures and processes, like the kind of surgical checklists described by Atul Gawande in The Checklist Manifesto. If you precisely follow the steps, the likelihood of failure drops precipitously.
Complex: The final and most difficult category, Edmondson writes, “Complex failures have not one but multiple causes and often include a pinch of bad luck, too.”9 Any time I’ve made fun of how bad Jewish leaders are at making predictions, it is largely in the context of a complex problem.
Since complex failures are complex (said Captain Obvious), it is difficult to identify one thing anyone can do to avoid them. As such, they are also kinds of failure that often lead to interpersonal blame that seldom illuminates and is rarely accurate, especially from inexperienced and overconfident people. Instead, Edmondson argues that the best way to respond to complex failures is by choosing “learning over knowing.”10
My favorite lesson from Edmondson on how to choose learning over knowing is pointing out people’s tendency to “optimize their own part of the system and do not step back to consider how their actions impact others.”11 This instinct is a perfect flaw to examine how seldom Jewish leaders examine complex causes behind a single, much-discussed problem. Looking at Jews in North America today, there are many complex “failures” that need to be analyzed.
To understand why a big failure occurred, all stakeholders must be willing to examine an entire system and everyone’s role. The alternative is the kind of narrow thinking and armchair quarterbacking.
Ultimately, we may learn that it’s just harder than it looks.
And maybe that’s the best first step towards learning from our failures.
Amy on Armchair Expert
2 Hours
In a survey of 10,000 desk workers around the globe conducted by Slack, workers said that once they spend more than two hours per day in meetings, they reach a “tipping point at which…[they] workers feel overburdened by meetings.”
Read the full survey here.
What I Read This Week
What Happens When Elmo Asks How You Are Doing: Elmo does it again! This time on Twitter. This piece was a powerful reflection on that moment.12
Anti-Semitism is Winning: Hyperbole aside, I think this piece by Dara Horn will go down in history as one of the most important articles written about anti-Semitism in the aftermath of October 7th.
Why Americans Stopped Hanging Out: No way to make a natural transition from the last article to this one, but I enjoyed this piece by Derek Thompson.
Stop Conditional Self-Worth: Do you only feel good about yourself when you get approval from others? Then you’ve come to the right place.
Pop Tart Appreciation: I never thought I’d post an article about pop tarts. But here we are.
If you need a refresher, read footnote 8 from a few weeks ago.
No, I’m not pulling your leg.
The question is more complicated than it appears.
For more information, read:
Andrew Porwancher, The Jewish World of Alexander Hamilton (Princeton: Princeton University Press, 2021).
The short answer is that Porwancher makes a convincing case that Hamilton’s mother was Jewish, thereby making Hamilton born Jewish if we go by matrilineal descent. However, once Hamilton settled in America, there was almost no evidence that he publicly identified with Judaism.
I never promised that there would be no math:
Been a while since I made that joke…
Ibid., 170.
Welcome to the two-timers club, a club of amazing thinkers who do not care about being included in this newsletter:
Annie Duke
Nir Eyal
Amy Edmondson
Robert Kegan and Lisa Laskow Lahey
Seth Stephens-Davidowitz
Yeah, being on this newsletter is just as prestigious.
Ibid., 18-19.
Ibid.
Ibid., 195.
Ibid., 234.
On a lighter note, then Elmo gets accosted by Larry David…