The One Mistake You Should Make

Are You Too Sloppy to Lead

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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: ā€œWe might be wrong, but we are not confused.ā€

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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