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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.

Today at a glance

• The People-Pleaser Paradox

• 1- Challenge your higher-ups

• 2- Align sideways

• 3- Bring people up

• Key Takeaways

• In Case You Missed Them

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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! 

Start the conversation, and watch people around you open. YOU start, people will FOLLOW

Product success isn't a solo act. We rise or fall together, folks.

If the product is great but sales are bad, did we really do well? No.
And if sales keep making big promises while we're still struggling, we don't want to celebrate that.

Our mission? To rally the troops, align departments, and steer the ship together. No formal authority needed – just solid leadership that speaks volumes louder than any title.

One simple framework:

✅ Count 3, 2, 1 in your head and just say what you need to say and Why?

3- Bring people up

Let's flip the script and talk about leading downwards. Sounds easy, right? After all, you've got the ‘manager’ authority.

But here's the kicker: too much authority can trip you up faster than you can say "team huddle."

Ever find yourself barking orders instead of empowering your squad?

The sweet spot? It's that delicate dance between guiding and empowering. People management is an art – and it often means stepping out of your comfort zone.

Sure, it's tempting to spoon-feed solutions, but will you sacrifice team growth? Instead, paint the picture, outline the roadmap, and let your team take the wheel (with a gentle nudge or two).

It might take a tad longer, but trust me – it's worth it in the long run. That’s your tradeoff!

One simple framework:

✅ Remember: Making people believe they can do more, is your 10x leverage

Key Takeaways

In Case You Missed Them

👉️ The Power of Summary (Link)
👉️ Career cheat codes for product leadership (part 2) (Link)
👉️ Career cheat codes for product leadership (part 1) (Link)

Get 1% Better Every Day. Execution Matters Most.