| After the disastrous Bay of Pigs invasion, John F. Kennedy learned a hard lesson: bad decisions often come from flawed decision-making. His inner circle had fallen into groupthink, where no one dared challenge the prevailing opinion. It was a sobering realization for a young president, and it stuck with him. So, when the Cuban Missile Crisis arrived in 1962—a moment where the wrong decision could lead to nuclear war—Kennedy knew he couldn’t rely on the same broken process. He made several critical changes to how he and his team worked through high-stakes problems. He created two competing teams—a red team and a blue team. The red team was tasked with presenting the case for aggressive action, like airstrikes or an invasion of Cuba. The blue team focused on more cautious approaches, like diplomacy or blockades. Each team dove deep into their perspective, offering strong arguments and detailed plans. Then Kennedy did something unusual. He asked the teams to switch sides. The red team had to argue for diplomacy, and the blue team had to make the case for military action. This forced both groups to challenge their assumptions and consider the issue from a different perspective. It wasn’t about “winning” the debate; it was about testing their ideas under pressure. But Kennedy didn’t stop there. He brought in an outside perspective. His brother, Robert F. Kennedy, and two other trusted advisors—National Security Advisor McGeorge Bundy and former Secretary of State Dean Acheson—were assigned a special role: to act as devil’s advocates. Their job was to poke holes in every recommendation that came out of the deliberations.“Find the weaknesses,” Kennedy told them. “Show me what we’re missing.” By encouraging dissent and rigorous critique, Kennedy created a process that forced his team to confront their blind spots and prepare for the unexpected. The result? A thoughtful, measured decision to impose a naval quarantine on Cuba rather than launching an immediate military strike. This approach bought the time needed for back-channel diplomacy, which ultimately led to a peaceful resolution. We all need to remember Kennedy’s lesson: bad decisions come from narrow thinking. By encouraging opposition, role-playing alternative perspectives, and inviting outsiders to test ideas, Kennedy avoided disaster. That’s the power of decision-making by design—a process that can turn complexity into clarity, even in the highest-stakes situations. For business leaders, the takeaway is clear: challenge your assumptions, foster dissent, and always create room for fresh eyes to spot the flaws in your thinking. When you do, you’ll make better decisions—faster and with far fewer regrets. The bottom line is that if you do not have a decision-making framework, you are doing your team, your business, and yourself a disservice. As I have stated in the past, I like the Cynefin Framework with the WRAP process from the Heath Brothers. However, there are many out there to choose from, and you will likely modify it. The key is to pick one, leverage it for leadership decisions, and when you have it well in hand, teach it to everyone in the organization. It will serve as a leadership development exercise as well. Be Exceptional! |