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Find a job with Annie · Aug 21, 2026

Nobody ever teaches you product

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Annie Li · Find a job with Annie

Nobody ever teaches you how to be a product manager.

This is bad for everyone who wants to pursue a product career AND for all of our companies.

5 years ago I became a product manager as well as the first product person in my company. The learning curve was extremely steep, I put down 4 digits cash for an online course, and was reading up about product management and startups almost non-stop in my free time. I thought my experience was unique.

5 years later, with 4 different product under my belt and having spoken to countless fellow PMs, I realized that almost no one gets properly coached and mentored on product work.

Speaking at a job search workshop. Photo by Austin Keeble

Some examples from my network:

Jane became a junior product manager after a few years of working in a different role. She is very analytical, has a lot of good ideas and is able to use AI to created detailed PRDs and even feature prototypes. However, she struggles to have trade-off conversations with her engineers. She also couldn’t defend her product direction with engineers despite the complex and shiny PRDs. It became extremely frustrating for both parties to the point that senior engineers gave direct negative feedback in a team call.

Alex moved into a product role from a project role at the same company. He has a very good understanding of the company’s product, existing team structures, and is known to be an easygoing and pleasant person who’s always eager to learn. Yet Alex seems to still only do the job of a project manager, where he makes very few product decisions and always delegates them to other stakeholders. Alex admitted that he lacks technical knowledge and is also unsure where his product decision-making power begins.

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As a former recruiter and current founder in the job search space, I constantly think about the concept of jobs, work, and our relationship to them. The lack of coaching and mentorship in product is both innate to the job and a direct consequence of organizational culture. Let me explain.

Think about the main ways of learning how to do a job, in society as a whole:

  1. Schooling, diplomas, professional training

  2. Mentoring on the job, either through peers or through managers

  3. Self study

Schooling is probably the most common type of vocational training. We were all told since we were kids that we should think about what job we want to do in the future, and study for them. Most of the professions within a modern tech organization can be taught at schools and universities: think marketing, coding, design, HR, finance, data, legal, business management.

Some roles require less prior domain knowledge and are usually acquired through on-the-job onboarding and training, such as sales and customer support. These roles tend to either provide new employees with speaking scripts, standard operational processes, or the hands-on guidance of a colleague or a manager, and have clear and quantifiable targets.

When we zoom into the product development trio of design, engineering, and product, we might also notice that there are normally multiple engineers and designers working within the same team or company. Design and engineering also have collaboration practices like design critiques, mobbing, pair programming and PR reviews. However, the ratio of product to engineering and design is often 1 to many.

This means the product manager is often on their own, left only to self-study or find mentoring outside the organization.

When I played Munchkins with colleagues, this card was played and my colleague said “That’s product managers!” Source: Reddit

Product work is inherently strategic, multi-disciplinary, and highly contextual.

The strategic aspect of product work requires PMs to make key decisions. This makes the existence of a junior PM almost paradoxical: how do you make decisions strategically when you have no experience?

Being a product manager also means you need to have some understanding of design, user interface, how software works, the technical implications of your trade-off decisions. The technical part is what scares a lot of PMs: you don’t understand a word from the engineers, but they’re looking to you for an answer and you’re worried you’ll embarrass yourself.

Product work is highly contextual, which means a lot of knowledge are domain-specific. You could be working on web apps, mobile apps, internal tools, B2B, B2C, enterprise software, note taking apps, or industrial sustainability compliance management software.

Beyond the nature of product work, the more confined career track within companies often leads to inherent competition between PMs. How can they feel comfortable helping each other learn, when there’s only one Head of Product position above them that they might compete for?

So what’s the solution for PMs who want to learn? Gathering my own experience and those from my network, this is what worked:

  1. Don’t be afraid of asking engineers what things mean. When your team looks to you for a decision, ask: “What’s the impact or implications of A vs B?” “Could you help me understand why this thing you mentioned is important?” Most engineers don’t judge. They know you’re not a technical expert, which is why you’re doing the product job and they focus on the technical stuff. It’s better to show you’re willing to learn than to pretend you know and make costly mistakes for the company.

  2. What made the biggest impact was also becoming best friends with my engineering managers or another tech counterpart. In my first year of being a product manager, my engineering counterpart is the CTO of the subcontracting company building the software for us. Being an entrepreneur himself, he understands the steep learning curves and was always open to discussing product and engineering topics, even staying on the call for 2-3 hours per week outside his billable hours just to share knowledge. Since then, I always tried to stay close to my tech counterparts. They can tell you how the engineers feel in private, and are often equally clued in on company strategy to be able to collaborate with you on roadmapping and prioritization.

  3. Treat self study as the default mode of learning instead of expecting structured teaching. Without a solid manager (the case for me in 2 out of 3 of my product companies), the only way to learn to be strategic without experience, to gain interdisciplinary knowledge, and to understand different contexts is to seek knowledge yourself outside of work.

    Product courses could be one way to find structure in your self study. When I learned to be a PM, I paid for the Reforge Product Management Foundations course and watched some sessions of Product Management A-Z on Udemy. Either course on their own wouldn’t have been sufficient, but I liked that Reforge put my sporadic product knowledge into a clear structure, albeit modelled after large companies; the Udemy course took Uber as a real life example throughout the course which was very practical.

    What helped the most was reading from and connecting with product folks at different companies, whether it’s reading their blogposts, social media posts, or going to product events. Some of my recommendations:

    • Teresa Torres, author of *Continuous Discovery Habits;*

    • Shreyas Doshi, ex-Stripe, Twitter, Google, Yahoo, focuses on “product sense” which drives good strategic decision making;

    • Lenny Rachitsky — no need to say more (although he became too AI-pilled for me recently and featured some very racist guests)

    • Will Lawrence, ex-Facebook PM, some of his Substack posts about building product experience from nothing were very inspiring

    • Crystal Widjaja, one of Reforge’s best instructors and is brilliant at product analytics

    • Rich Mironov, product OG and lecturer, I liked his LinkedIn posts on AI

    • Enzo Avigo, founder of product analytics tool June.so and now acquired by Amplitude, he had some really in-depth LinkedIn posts during June days

    • LeadDev, this is a developer-focused organization but I was hooked by its insightful articles on inclusive engineering practices and gave me a lens into understanding the wants and wishes of engineers.

If you’re a product leader or looking to enter senior or leadership roles, we need to find ways to actively facilitate collaboration for our fellow PMs. What kinds of learning or knowledge sharing sessions can we create? What could we do for PMs to review each other’s work more and get our product people to become more effective faster? I would love to hear your ideas.

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