- Another PM Day
- Posts
- The One Mistake You Should Make
The One Mistake You Should Make
Are You Too Sloppy to Lead


My favorite weekly finds
🛠️ Tools
NotebookLM (Google’s AI tool) now creates Mind Maps, turning your sources into a visual branching diagram.
Use Brainnote as an AI thought organizer to summarize your ideas in seconds
Prezent (Try for free) converts your ideas into branded presentations effortlessly.
Record.ai (WhatsApp assistant) remembers things for you, while 🔗 Epiphany (voice memo saver) transfers your recordings to Slack, Notion, Asana, and more.
timeOS (Mac-only for now) auto-generates meeting summaries (no bots!), supports 60+ languages, and embeds playback—free for 10 AI meetings (90 min each)
Fathom (One of the most popular meeting AIs) captures, transcribes, and summarizes your meetings—if you don’t mind the bots.
📰 Intelligent Insights
Is AI behind the post-pandemic productivity boom? Fed economist Austan Goolsbee thinks it’s at least one of four key factors.
Why Apple’s AI lag actually matters—here’s the breakdown.
A fascinating ~40min dive into the Superintelligence Strategy doc—a three-part framework for AI risk & security.
AI leaders on why today’s tech won’t reach AGI—read their takes.
👀 ICYMI
When your CEO doesn't get it (learn more)
Team Topology: The Secret Sauce to Product Success! (learn more)
Fail Smarter, Winning Through Mistakes (Learn more)
The One Mistake You Should Make
Why should I care?
I finished elementary school with a perfect report card, but getting there wasn’t all smooth sailing.
While I aced every subject, gym class tripped me up—I had to do a headstand and a handstand.
Despite being a top runner, I couldn’t do them and nearly lost my perfect score.
Being a perfectionist was hard.
I spoke with my gym teacher, and we struck a deal: if I learned a headstand by year’s end, I’d earn the A, even if the handstand stayed out of reach.
With my parents forbidding wall practices at home, my grandmother came to the rescue.
Every weekend, I practiced by her door until I finally mastered it and earned my top grade.
This experience taught me a vital PM lesson. In product management, you can’t always hit perfection.
Flexibility matters because not every mistake is the same. As a product leader, knowing when to adjust standards and when to push hard is key.
Let’s dive in.
1- Take calculated risks to move forward
In tech, you have to take calculated risks to move forward. The future is unknown, so risk is part of the game—even if you sometimes fail.
Think about a poker table. As Annie Duke shows in Thinking in Bets, every move has odds.
Even if your best move has a 70-30 chance, sometimes you lose despite doing everything right.
That’s just how things work.
In product leadership, if you’re not willing to risk, you’ll fail. You need to know your risks and assumptions.
I like Tomer Cohen’s words: “We might be wrong, but we are not confused.”
You must make informed decisions—even if mistakes happen later. Not deciding can cost you more.
So, weigh what you’re betting on and be ready to adjust.
That's the secret to smart risk-taking in product management.
2- You Don't Know What You Don't Know
Even when you stick to clear facts, you’re bound to miss something.
Uncertainty isn’t just about the future—it’s in the complex details of today.
No one—be it from product, the CEO, marketing, or sales—can know it all.
With so many viewpoints, blind spots are a given.
The key is to know your blind spots and plan for them.
Write down your assumptions and chat with your team.
Separate assumptions from facts, and ask others to point out what you might have missed.
That’s how Veeva stays sharp in product management.
Until you accept that, you can’t help anyone align.
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