Challenge your higher-ups

The pitfalls of being a Yes-Person

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Challenge your higher-ups

Hello Product Leaders!

I once coached an amazing senior product manager, let’s call him named John.

He was great at working with others and caring about their success. But even the best of us face challenges, right?

John was frustrated because his projects were stuck but instead of diving deep into the nitty-gritty, he held back, fearing he'd step on people's toes.

Turns out, his likable nature, which helped him succeed so far (as he was great at execution), was now holding him back from getting to the next leadership sphere.

So, I gave him a challenge.

Push the boundaries and don't be afraid to make waves. And you know what?

It turns out that showing some personality can really make a difference.

The key is finding the right balance between respect and being a little rebellious, and then you'll see your product leadership soar!

Let’s dive in.

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The People-Pleaser Paradox

The challenge is finding the right balance between being too accommodating and too assertive.

Both come from avoiding conflict and seeking approval, but in the end, you won’t show leadership or will have a team that resents you.

It's quite a paradox, isn't it?

But the worst is people pleasers are at a higher risk of burnout, says Harvard-trained psychologist.

✅ In short, speak up and be opinionated. This increases self-esteem and self-confidence.

1- Challenge your higher-ups

Let's dive into a challenge many of us face: navigating authority from the top down. Yes, those at the helm hold the cards, but here's the twist: they need us more than they let on.

Ever felt like a cog in the machine, just following orders? Well, guess what?

The higher-ups are feeling the pinch too. They know a ship can't sail smoothly if the crew feels like robots.

Here's the kicker: if you're just a yes-man (or woman), you're not doing yourself or them any favors.

They are not just looking for order-takers, they're seeking partners, who crave your insight, your challenges, and your ideas.

That’s what I look for as well in my team.

One mental framework:
Don’t work for your manager, you work WITH your manager

2- Align sideways

Ever feel like you're the lone ranger in a world of sprinters? You're not alone.

As product leaders, we're at the epicenter of it all. We see the big picture, the gaps, the missing links. And guess what? It's our job to call it out.

Here’s a classic. Think you're the only one scratching your head about the company's direction? Think again. Odds are, your colleagues are just as puzzled.

So, SPEAK up!

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