Tools & Thoughts for Leaders

Product Leadership is…

TTL 14

Expanding the ground for your products.

👋 Good Morfternight, this is Paolo Belcastro, with the fourteenth issue of TTL: Tools & Thoughts for Leaders, your weekly leadership fix.

Today, we’re going to deal with a question that’s close to my heart, and that I am still working on answering satisfactorily:

What exactly does it mean to be a product leader?

But Paolo, you might say, you are a product leader.

You are right: in my roles at Automattic, I’ve helped build products like WordPress.com, Jetpack, and the .blog registry, and let me tell you—if I had a buck for every time I thought I’d found the definite answer to that question, I’d be writing this from my second yacht 🙂

So, today’s issue of TTL is my imperfect answer to that question.

Expanding the middle of what?

At its core, product leadership sits right in the center of three primary overlapping areas that summarize any software business:

  • Customer needs
  • Business goals
  • Hardware & Software infrastructure

Your job as a product leader is to expand that area.

You need to make sure that your product resonates with customers, aligns with your company’s business objectives, works seamlessly within the infrastructure you have, or that the appropriate investments take place. The better aligned these forces are, the more expansive the product’s impact will be.

The problem?

The center is not static, it is in constant evolution, as these three primary areas (and other secondary ones) act as gravitational forces pulling you in opposite directions.

So, it gets messy.

It’s all about the customers.

If there’s one rule in product leadership, it’s this:

It’s all about the customers.

You can have the most beautiful, technically flawless product in the world, but if it doesn’t solve real customer problems, it won’t sell.

So, what’s the most critical task? Truly understanding your customers.

Conduct research. Use customer insights, surveys, and data analytics to understand their needs. Never assume you know what they want—because you don’t, not without actively listening to them.

This is where feedback loops come in.

Keep the feedback cycle short. Talk to customers early, often, and directly. If a feature doesn’t work, they’ll let you know fast—no need for countless meetings to discuss why something didn’t land.

Feedback cuts down on over-complicated solutions and keeps your product grounded in reality.

Customer needs evolve, and your job is to evolve with them, not to guess what they’re thinking from a distance.

Business goals: focus on the right things

While customers are your North Star, you’re also running a business that needs to thrive. Every product must align with larger business goals, whether that’s increasing revenue, expanding market share, or driving user engagement. These goals define what makes a product truly successful.

The major difference between the companies which succeed and those that fail is rarely how hard people work. Most often than not is about working on the right things, or wasting energy on irrelevant ones.

To impact business metrics positively, and materially, you must focus on the right things, prioritize high-impact work.

Easier said than done.

Focusing on the right things.

As Julie Zhuo points out in her article, The Blind Men, the Elephant, and the 3 Data Mistakes, we often base decisions on incomplete perspectives.

Like the blind men in the parable who each touch a different part of an elephant and mistake it for the whole, we can fall into the trap of viewing only part of the data.

As a product manager, it’s crucial to see the bigger picture and not just pieces of the puzzle — make sure your team is, too.

Being disciplined with your data and constantly cross-checking your intuition is painful, but it is the only way to make sure you’re focusing on the right thing.

Doing the important things first.

Now that you have all the data, you have to start working somewhere.

Enter the classic Glass Jar Parable: imagine you have a jar, and your goal is to fill it with rocks, pebbles, and sand.

  • The rocks represent your high-impact projects—the initiatives that will significantly move the needle. These are your biggest priorities, the ones that align most closely with business goals and customer needs.
  • The pebbles are your medium-priority tasks—important, but not game-changing. They contribute value but don’t have the transformative potential of the rocks.
  • The sand represents the small, day-to-day tasks—necessary for operations, but not groundbreaking.

Focus on getting the rocks in the jar first. If you start with the sand or pebbles, you’ll run out of space for the rocks.

That’s precisely what happens when you slip into firefighter mode. You know, when you’re constantly putting out fires instead of working on long-term projects. I’ve been there, and I know how tempting it is.

But finding the time and focus to work on the rocks is a defining feature of a successful PM.

Keep the machine running smoothly

Hardware, and software, infrastructures may not be the sexiest part of product management, but they are crucial.

Every feature you ship needs a solid foundation to stand on.

As a product leader, part of your responsibility is ensuring that your product remains technically sustainable and scalable.

This means constantly balancing your act between your desire to move forward as fast as possible, your wish to provide an exquisite user experience, and the need to increase scale and stability.

In theory, we have it all sorted out: testing hypothesis with cheap prototypes, find market-fit with MVPs (minimum viable products), then refactor, or even rewrite, everything once you achieve growth.

The reality is much messier than that.

You need to master when to accelerate and when to slow down.

We all want to build great quality products, but there is no virtue in doing that if the time it takes to bring them to market exceeds your runway. “Let’s ship it, we can fix it later” is often met by rolling eyes, as everyone knows that piece of code will still be there years from now.

The reality is that once you are over the initial phase, and start growing, if you do not reach a balanced distribution between innovating through new features, improving the experience by polishing your existing ones, and paying back some of that technical debt, you will not succeed.

Remember, those forces pull in opposite directions, and that space in the middle of the diagram at the top wants to disappear.

It’s your role to find the balance and expand it instead.

Most of the time it will be a lonely battle, and you might not get applause for it, but trust me, you will thank yourself in the future.

Lessons from cheesy movies

Some time ago, I linked an X post in Morfternight (my old newsletter) where Jason Knight used “Love Actually” to teach 9 lessons to Product Managers.

He was simultaneously hilarious and fitting.

I suggest you check it out for a more lighthearted take on “what does it mean to be a product leader?”.


That’s it for today.

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Here on TTL, we dig into practical leadership tips and effective strategies, with a particular focus on tech leadership and managing distributed teams (that’s what I do every day, add me on LinkedIn).

Whether you’re steering a tech startup or leading a remote team, these insights are designed to help you navigate the complexities of modern leadership.


I also publish on paolo.blog and monochrome.blog

Cheers,


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