The All-In Podcast on Thinking Clearly, Debates and Memos -- Big Bet Style
Rewire Your Brain by Working in Memos
Like many of you, I’m a fan of the All-In Podcast. Fast-paced, debate-oriented, divergent opinions welcome, independent thinking — this is my go-to Saturday morning workout podcast.
I made a note to revisit the June 23, 2023 episode, where they dropped a truth bomb—a brilliant five minutes of pure wisdom. They discussed the essence of fostering a culture centered on clear thinking, encouraging healthy and respectful debate, and tackling tough problems head-on.
All by writing memos.
It was a moment that resonated with me—right in my swim lane!
Why Memos
Amazon is known for its “working backwards” approach to customer-centric problem solving and innovation approach. The backbone of Big Bet Leadership is a set of memos prescribing a specific approach and format on these memos for complex situations and for a team without the background in doing these. It takes practice and is a different, powerful way of working. Making this switch is a change in how you work.
Effective communication is more critical than ever. Yet, it's also become increasingly difficult to achieve. With the constant barrage of emails, Slack messages, and Zoom meetings, the clarity and depth of our communication often suffer. This is where memos come in—an underappreciated yet incredibly powerful tool that can transform the way we lead and make decisions.
The appendix of *Big Bet Leadership* provides a compelling case for why working in memos is so effective. But before diving into the research and benefits, let's first understand what a memo really is. Unlike a brief email or a chat message, a memo is a thoughtfully crafted document that conveys a comprehensive, well-structured argument or idea. It’s not just about transmitting information; it’s about creating clarity, fostering deep understanding, and enabling informed decision-making.
The act of writing a memo forces clarity of thought. When you're required to explain a concept or a decision in a few pages, it compels you to think through every aspect of your argument. You can't hide behind jargon or vague language. This process alone often helps leaders identify gaps in their reasoning, uncover potential risks, and anticipate counterarguments.
Research supports the idea that writing is one of the most effective ways to enhance understanding and decision-making. Among several surprising benefits, research published in the Journal of Consulting and Clinical Psychology suggests that the act of writing can make you feel happier and less negative! That’s just one of the side benefits. Perhaps that is why I enjoy writing this newsletter.
Highlights from The All-In Podcast
At ~1:00 hour into this podcast, the discussion turns toward working in memos. I recommend listening to it. Here are a few critical quotes. Read this carefully as they make several important observations…not just one.
When you write a deal memo, compared to doing a deck, the questions you get are so qualitatively different, and the people you attract are so different, it is extraordinary. I am advising startups across the board to write really tight deal memos.
We write these deal memos internally when we make an investment. But man is it great for clarity of thought and for the person on the other side to just stop and read a thousand or two thousand words, as opposed to having to go through a stupid performative deck, it is just such a better process.
— Jason Calacanis
It allows you to find people who will critique things in a thoughtful and intelligent way. It’s hard to critique decks because you use broken English, fancy graphics. All of a sudden someone who is very good at graphical layout can dup someone else. And so you don’t get to good outcomes of this weird group-think effects that happens when you look at decks. I’m not a fan of decks. I use them but they need to be a companion to some sort of long form narrative document. I just think it’s more useful.
You get people who can really think about what they agree about, what they don’t agree about; it shows the intellect of the person writing it. It’s like a basic skill that people should have. Decks are very dangerous. If you’re going to make decisions, I would encourage that the bigger the decision, the deck is insufficient.
The long form documents don’t need to be long — 2, 3, 4 or 5 pages. But without it you’re going to allow some really bad decisions to creep in along with some good ones.
— Chamath Palihapitaya
The Hard Work
Here’s the catch, the rub, the reality of working in memos. It’s HARD. This way of working requires a rewiring because you have to focus and create blocks of uninterrupted time for not just the writing, but the reading and the debating.
UNITERUPTED.
It’s hard but completely feasible. Give it a try.
And I have FREE STUFF to help! The Big Bet Journal has a set of memo templates; the Big Bet GPT is your creative writing and problem solving associate; the Big Bet Prompts connect them all together.
Tune In
Download the Substack App and start tuning into the notes that I drop throughout the week. I had a couple of great ones this past week.
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Onward!
John
About The Digital Leader Newsletter
John Rossman is a writer, business advisor and keynote speaker. The Digital Leader Newsletter is a weekly coaching session focused on customer-centricity, innovation, and strategy. We deliver practical theory, examples, tools, and techniques to help you build better strategies, plans, and solutions—but most of all, to think and communicate better.