Your leaders aren’t the problem. Your leadership group is.

Satyajit Rout
2 min readJan 23, 2023


On January 10, 1961, the New York Times outed on its front page that the CIA was training Cuban exiles to launch a guerilla war against the new Fidel Castro-led government in Cuba. The headline should have chucked this covert plan of the John F. Kennedy-led US government to the dustbin. Only it didn’t.

Three months later, 1400 of the so-called guerillas landed to find 20,000 of the Cuban army waiting. In three days, all were dead or imprisoned.

The US had egg on its face. A subsequent inquiry revealed there was ‘cozy unanimity’ among the leadership group advising the President.

The NYT headline didn’t elicit a review. Even the contingency plan should the guerilla landing fail was based on a draft version of the action plan that had been changed since.

The infamous Bay of Pigs invasion had failed because of 𝐠𝐫𝐨𝐮𝐩𝐭𝐡𝐢𝐧𝐤.

The disaster pushed Cuba closer to the Soviets and 17 months later led to an even bigger standoff–the Cuban missile crisis. For 13 days, the world stared at a nuclear war between the two most powerful nations. It was averted by smart decision-making by the same leadership group that had been (ir)responsible for Bay of Pigs. Tellingly, Kennedy had not sacked those behind the Bay of Pigs fiasco.

❓As a founder, CEO, or leader, you may wonder: What did President Kennedy do to get the best out of his group of advisors?

According to Irving Janis’ 𝐕𝐢𝐜𝐭𝐢𝐦𝐬 𝐨𝐟 𝐆𝐫𝐨𝐮𝐩𝐭𝐡𝐢𝐧𝐤, the US President saw both sides of groups and preserved the best of each. After Bay of Pigs, he changed the decision-making process but left the decision-makers untouched.

✔Licensed people to question across the pecking order
✔Appointed devil’s advocates to pursue contrarian lines of inquiry
✔Brought outsiders in for fresh perspectives
✔Made a habit of leaving the room to allow free exchange of ideas

Like President Kennedy, you can aspire to the best of both independent thought and healthy skepticism by getting your leadership group to adopt:

1️⃣Shared vocabulary–agree on a common language. The US Joint Chiefs of Staff told Kennedy they had a ‘fair chance’ in the Bay of Pigs invasion. Kennedy was buoyed by their assessment. Later, he found out they meant a 25% chance of success.

2️⃣Role assignment–appoint devil’s advocates whose job it is to counter-question.

3️⃣Precision questioning–drop ‘I don’t think so’ or ‘Do we all agree?’ for ‘What do you mean by X?’ and ‘What has to change for your opinion to change?’

4️⃣Clear accountability–be clear about who the decision-maker is to break a deadlock

5️⃣Incentives for problem prevention–reward people to do the unglamorous job of nipping problems in the bud.

What do you do to help your leadership team make the best decisions under pressure?



Satyajit Rout

I write about decision-making, mental models, and better thinking and things in between