#35 - When you feel like you're not growing as a Product Manager

What you might be going through

Product development is abstract and complex, and as a junior PM, you might face a steep learning curve filled with late nights and information overload. If you can push through this initial phase, you start to find excitement in your progress—constantly learning, stepping out of your comfort zone, and seeing your growth in real-time.

But often, after a few years, you hit a ceiling. You know what to expect, you’re still tackling new challenges, and you’re in the weeds of shipping new features - but something starts to feel missing. You might think, "There must be more to this."

That’s when you begin to do more research about Product Management. Maybe you reach out to fellow PMs, some of whom are doing similar things, while others seem to be involved in more exciting, innovative work. You read books, take online courses, and dive into blog posts. Terms like “product discovery,” “jobs-to-be-done,” and “strategy” come up frequently. "Jeez, I never get to do those things!" - you mutter to yourself.

That’s when the FOMO starts to creep in."Should I switch companies? Am I missing something?" But to switch jobs, you feel you need to upskill—to get better, to become more prepared for new opportunities. BUT WHAT SKILLS SHOULD YOU LEARN?

I've had the privilege of mentoring and giving advice to hundreds of junior PMs, and the story above draws from many real experiences.

How to grow as a PM?

It’s natural to wonder, "What skills should I improve to grow as a PM?"

But I think it's not the most useful framing. The question assumes implicitly that growing as a PM is about upskilling. However, in Product Management, skills are deeply tied to the context in which they’re applied. If you say you've learned about Product Discovery, any Product Manager who's worth their salts will ask, "So how did you apply that, and what were the results?"

There's also another layer to consider. Being able to learn and apply skills depends largely on how your company operates and the obstacles it faces. You can't simply decide to practice Product Discovery in a vacuum. There has to be a relevant problem where Product Discovery is the right solution within existing organizational constraints.

The key is to reframe the question "What skills should I improve to grow as a PM?" to: "What does growth look like for a PM?"

For me, growth isn’t just about acquiring skills - it’s about the ability to tell a story of how you identified and tackled real organizational problems, within real organizational constraints, and what you've learned from that. If you are not actively engaged in solving an organizational problem, it becomes almost impossible to determine whether you've genuinely grown.

I'm emphasizing organizational problems because that's the context you're operating within. Whether you realize it or not, organizational problems drive your day-to-day work, like they drive everything else that a company does. Some examples that I've seen myself:

• A company might struggle with user growth when approaching a new round of funding. To address this, it might double down on marketing efforts and freemium products to attract new users. As a PM, you could find yourself focused on acquisition-related initiatives to support this growth.
• Another company might face competition from a new entrant with little technical or product debt, enabling it to release features at a rapid pace. In response, your company might decide to spin off a separate R&D lab with full autonomy to explore new technologies and applications. Your role as a PM could shift to identifying new customer use cases that the R&D team can tackle.
• Or, a company may have succeeded with one core offering but struggled to replicate that success with a new product. Realizing the new product isn't panning out, it might redirect resources to optimize its main revenue driver instead. As a PM for the newer product, you could be tasked with integrating it back into the core offering and halting new feature development for your own product.

So if you're already being affected by these organizational problems, why should you still think about them?

If you're a junior PM, chances are you'd be in the weeds getting projects delivered on time and keeping the lights on. Being incredibly hands-on unfortunately means that you may lose sight of the bigger picture. Many juniors/executives I've spoken with cannot answer the question "What are the problems that your company is facing?". Even if they're able to identify the problem, they often can't follow up when being asked "What have you done to tackle these problems?"

I'm not saying focusing on project management or product delivery is wrong, because these are valuable activities. I'm just saying, if you're curious about what's the next level, then the answer may lie in trying to tackle existing organizational problems, rather than obtaining new skills. Speaking of which, you'd probably have to do that anyway if you're determined to address a hairy problem, but the nature of that problem dictates which skills you need to learn, not the other way around.

Being able to tell the story of how you overcome an organizational problem is the clearest sign of growth

What did growth look like for me?

Growth can come in different sizes and shapes, depending on your company. Let me tell you a real story so that you know what growth looks like for me. This is a short version that's rid of all the gritty-nitty details, but it should demonstrate the point:

At no point in the story above did I say that I practiced problem discovery or anything, but if someone were to tell me a story like that, I would instantly understand that they must have put some sort of discovery techniques into use. I'm not telling you to learn Product Discovery specifically either, I'm making a larger point that growth is best observed macroscopically, rather than through a microscopic lens of upskilling.

A few additional points

I have a few additional thoughts on this topic that are a bit scattered, so I'll put them in bullet points as follows.

• I'm not describing an interview technique.
  • Interview techniques, such as the S.T.A.R framework, provide ways to package and structure your experience so that you can present your best self to hiring managers. I'm telling you to construct your best self and play an active role in overcoming organizational problems.
  • Actively determine the scope of the situation on an organizational level, expand from task-oriented thinking to identifying major challenges, take actions to tackle them, and then live out the consequences of your decisions.
• Don't wait until you have a job interview before you think about this, most meaningful product decisions take months or even years to unfold over relevant dimensions.
• What if you're not empowered?
  • In some situations, people may deliberately disempower you from working on organizational problems. For example, if you have a line manager that cares more about protecting his ass rather than doing what's best for the company, then it's very difficult to take my advice. When put in a leadership position, such a person often desires to maintain the status quo and discourages his subordinates from disrupting the current situation. I've been in that position myself, so I understand how disempowered it feels to PMs.
  • However, consider your circumstances and use your best judgment to determine if that's a hard constraint. Sometimes your line manager wants you to succeed but is simply swamped in their daily duties. If that's the case, you can simply be more proactive in communication, taking some workload off them and giving them space to think about more strategic problems. Having gained trust, you'd also likely be in a good position to help them solve these strategic problems.
  • Empowerment is rarely a yes/no thing. Empowerment is often a function of trust and fire-fighting. The more trust and the less fire-fighting you have, the more likely you'll gain empowerment.
• What if you don't have a mentor to provide feedback?
  • Having a good mentor is rare. What you can do is crowdsourcing feedback. Consider joining Product communities where other like-minded PMs hang out, and make the best use of it. Provide a lot of context, and ask a lot of questions.
  • Reflect and write a lot. Writing is good for personal growth because it's a forcing function for clarity. The process of writing, not the output, helps you figure out your problems, or at least it helps shatter what you may perceive as a problem. Psychological constraints may make a problem seem intractable, and a shift in perspective could be the key to your blockade.
  • Also, guess what's also good for packaging and structuring your experiences to present your best self to hiring managers? Yes, also writing. A junior PM that I know attributed her successful job interviews to writing.
  • Once you've written it out, you can be your mentor and provide feedback.
  • My newsletter is full of stories about problems that I encountered, and how I attempted to overcome them. From problems when working on my startup, to problems when trying to start my course, to problems when working in our community. Sometimes I wasn't able to overcome them. In a sense, this newsletter is a live documentation of how I'm growing as a Product Manager. I have a library of growth stories to showcase to hiring managers.
  • The reason I'm bringing this up is that I had no Product Management mentors. My old boss gave me a chance to become a Product Manager, but we were figuring out how to do Product together. If I can do it, I think you can do it as well.

Conclusion

I hope this helps you consider a more useful framing to achieve growth as a Product Manager. I never really thought much about upskilling, and have always focused on solving the organizational problems that are present. Sometimes I fail, sometimes I succeed, but growth is always the constant.