When in Doubt, Write It Out: Writing as the Ultimate Leadership Tool

As leaders, we often face tough choices that can shape the future of our organizations. Recently, I finished reading Thirteen Days by Robert F. Kennedy, which provided powerful insights into how a well-structured decision-making process can lead to better outcomes.

Here’s what I learned and how it applies to leadership.

During the Cuban Missile Crisis, President Kennedy’s advisors presented him with two urgent options:

1. Naval Blockade

2. Preemptive Military Strike

Faced with a decision that could have sparked a nuclear conflict, Kennedy didn’t rush into action. Instead, he asked his team to refine their recommendations.

The Decision-Making Process That Worked

Robert F. Kennedy detailed the process in Thirteen Days. Here’s what the team did:

• Broke into smaller groups – Each team wrote up their respective recommendations.

• Exchanged and critiqued papers – Groups dissected each other’s ideas, offering critiques and refining proposals.

• Iterated their work – After feedback, each group refined their papers into more definitive plans.

What Stood Out to Me

Tough decisions are inevitable in leadership, whether in business or nonprofit organizations. How you approach those decisions can determine the quality of the outcome.

• Writing down ideas isn’t just a formal exercise—it brings clarity and forces critical thinking.

• This process of refinement and iteration encourages deeper analysis, ensuring that the final decision is well-informed.

This approach allowed him to make the best possible decision, avoiding rash actions.

Similarly, Jeff Bezos at Amazon banned PowerPoint presentations, opting for written memos instead. Why?

• Writing forces clarity – It ensures that every idea is fully thought out before it’s presented, which reduces the risk of half-baked ideas or superficial thinking.

• At Amazon, memos ensured that every idea stood on its own merit, without the distraction of flashy slides.

Why Structured Processes Matter for Leaders

As leaders, adopting structured processes—yes, even writing and exchanging papers—ensures:

• Clarity

• Reduced bias

• Better choices

Writing forces you and your team to think more deeply, analyze critically, and uncover insights that might otherwise be missed.

Takeaways for Leaders

The next time you’re facing a tough decision, don’t rush. Take a page from the playbooks of Kennedy and Bezos:

• Write down your ideas.

• Refine through feedback.

• Iterate and improve.

• Seek clarity before deciding.

In doing so, you’ll ensure the best outcome for your organization.

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