What I've learned transitioning from a founder to product manager

12, often paradoxical, lessons.

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In 2017, I co-founded a startup called WECAST, and for the next 3 years worked as the CEO and Head of Product.

That was probably one of the most important experiences I’ve been through. It gave me exposure to many aspects of business and building a product, and I was constantly learning — mainly about how not to do things.

This was from a startup perspective of course — where things are different. You have less resources, you’ve got more scrappy processes and things change a lot faster

In 2020, due largely to luck and good timing, we got to join the largest company in the market that is working towards the same mission we were at WECAST, and shared a similar market hypothesis. Meaning we could continue the work we were doing but at a much larger scale.

I joined as one of the first product managers, transitioning from a small startup team into a larger team with world-class people, and a high-performing product culture.

After a year and a half working, learning, and unlearning with my new team, I can reflect on how I did things as a founder versus now as a product manager.

Here are 12 “lessons” I’ve learned — let’s dive in! 👇

#1 Listen to your customers 👂

The importance of speaking and listening to your customers continuously cannot be overstated. Whatever you’re building, you’re building it for someone. And being in sync with this person’s problems, needs, and goals is at the core of building a meaningful product.

Developing empathy for your customers and prioritizing what matters to them as you move through product discovery, planning, execution, and iterations ensure that you’re building something to last.

There are numerous ways to listen to your customers (such as interviews, surveys, internal data), some more scalable than others. Even still, nothing can replace direct conversations.

These conversations help discover problems and, with the right questions, can provide access to long-tail insights that play a key role in informing product and strategic decisions

#2 Stop listening to your customers ✋

Not everything your customers tell you is actionable — and trying to act on everything is highly problematic. Being able to disseminate between actionable feedback and ideas, triage this feedback, and prioritize is a critical role of a founder or product manager.

Identifying trends in conversations, blending feedback with your product judgment, and thinking holistically about how this fits into your organization’s mission, goals, roadmap, etc. is key. For example, at my first startup, we frequently had feedback from customers on the buyer-side of the marketplace asking for a feature that solved a specific problem. Specifically, they asked us to build out a payroll feature to make bookkeeping easier. However, while this was a problem they wanted to be solved, that wasn’t the business we were in. And going after that with limited resources (while appealing to build something people are asking for) would have taken us down a path we believed was strategically wrong. This would have actually negatively affected how useful our product was at solving the problem for them we were focused on.

So listen but through a well-tuned filter.

#3 Watch the competition 👀

Having competition is a good thing — it’s indicative of the problem you’re trying to solve and the opportunity for solving it, and you need to know your competitors exceptionally well.

Having an understanding of their mission, who their customers are, and how well they are solving their problems and meeting expectations is a critical part of your job.

There are lots of ways to learn about your competitors, either through more comprehensive competitive analysis during initial market research, or importantly, by having a finger on the pulse continuously. To name a few, regularly checking their websites and blogs, subscribing to Google Alerts, checking forums and reviews, and watching their Crunchbase account for funding announcements.

Watching competition is easy, the harder part is knowing when to not pay attention.

#4 Ignore the competition 😎

There are lots of times when ignoring what your competition is doing is the right decision. By ignore, I mean to acknowledge, understand, and continue without changing course.

Sometimes copying features or strategies is the right move, it’s nothing to be ashamed of. Our jobs don’t require us to come up with endless novel ideas. Sometimes piggybacking on competitors’ successes and leveraging their market research is the right move. However, in order to do that in a healthy way, you have to know their customers and understand what business your competitors are in. Otherwise, you’re vulnerable to a dangerous path that can easily lead you astray from your core market thesis and roadmap.

We are tasked with having a continuous mental (but often documented) gap analysis with our competitors. A strong founder or PM knows when to close it, and why they are (or aren’t) making that decision.


#5 Get Paid 🤑

Getting paid for what you build and bring to market is the quintessential measure of the value you’re creating and capturing as a business. Cash flow allows you to invest in your team and product. Plus, it gives you more room to take risks, learn, build, measure, and iterate your product until you find product-market-fit.

And if you’re a startup considering the venture route, showing that you’re post-revenue with real people paying for your product or service will give you the term sheet you want.

Knowing the business model of your solution and how it’s going to be monetized is critical, as your responsibility to the company is to get those customers paying, and as fast as possible.

Cash flow is king — but, so is timing.

#6 Don’t worry about getting paid 😌

This is analogous to finding what you’re passionate about and working on it, the money will (hopefully) follow. Doing it the other way around doesn’t always lead you to a long-term desirable outcome.

Something similar can be said about building products. When a product is early in its life-cycle, often it’s a better decision to focus on getting some traction with real users and making sure you’re building something that people actually want

Once you’re doing that, and hopefully for (1) enough people that (2) see the price of your product greater than the value it creates for them, then you’re on a good path to creating a valuable business and getting your first dollars in will be a much easier business.

#7 Be a customer advocate 🦸‍♀️

Nothing substitutes for understanding your customers. And a good founder or product manager should be in sync with their problems and needs as well as represent the customer as if they were a silent bystander listening in on product-related decisions.

To create a product people want and love, you need to be customer-centric. That means always considering the impact on them and their perception of your product or service. They surely have an opinion, and your job is to communicate that to the team when necessary and advocate for what is best for the customer.

For instance, when you’re working with designers, a useful way to ensure the customer is being considered is to ask, “As a customer who wants to do X here (likely under Y circumstances/conditions), does this help me, and is this clear and easy enough for me to achieve that? And what could help make my job here more efficient?”

#8 Say no 🙅‍♂️

Saying yes is easy and it can feel like you’re doing the right thing, being inclusive, and listening to your team and customers. But, saying yes can take you down a long road of extensive scope creep, wasted engineering and team efforts, and ultimately wrong product and strategic decisions.

Everyone will have ideas and feedback, and to make saying no harder, often really good ones. Your job is to triage that (instantly when possible), figure out what’s actionable and what’s a priority, and decide on the next steps.

Importantly, it’s not about saying no just because you think otherwise. Ask questions, get a better sense of where the other person is coming from, and how they’re thinking about the problem. Be sure to efficiently communicate your decision and the rationale behind it.

You’re not a unilateral decision-maker and people need to feel heard, understood, and ultimately be behind in the decisions that are made to keep motivated.

#9 Move faster 🏃‍♂️

Learning is the name of the game. You want to be building and getting products into the real world as fast as you can to maximize learning with the least amount of effort and resources.

This allows you to start measuring by getting data and feedback, speaking with customers, and making iterations as you determine the right solution is for your driving problem.

Timing is often a key component to the opportunity at hand. Imagine you realized your target audience was facing a new challenge because of the pandemic — if you’re fast enough you might be the first team to solve it and bring in new customers. If you’re too slow, you miss the boat entirely.

You likely have an overall vision for what your product will look like and the various problems you’ll solve for your customer, but to move faster, really focus on one core problem and your hypothesis. Also, keep your scope as small as possible to validate what you believe to be true. My other piece, “7 Steps to Running a Successful MVP Experiment and De-risking your Next Idea,” can offer more insight.

#10 Ship incrementally 👷

Imagine you wanted to paint your house a new color and surprise your partner. Would you labor away and paint the whole thing, giving one big reveal with a “Tada, what do you think?!” Or, would you try to see if they liked the color first.

I heard my manager and CTO say this once and it really rang true for me — “It’s easy to go forward, it’s much harder to go backward”.

And this applies to engineering effort, team motivation, and the customer experience.

Before something is shipped, you really don’t know how your customers or the market will respond. It might be a fantastic new feature but it just never sees the adoption or engagement you expected. Moving fast and shipping incrementally de-risks that for you.

Say you ship a feature with all the bells and whistles you wanted, it’s live for a period of time, but based on the feedback you realize it requires significant adjusting to fit the customers’ needs. This is wasted engineering time that requires undoing and re-coding. This can cause frustration as your team may have spent many hours under your direction working. Not to mention, there may be some customers who are using the feature/product and getting value from it, now to be pulled away from them.

#11 Make data-informed decisions 🧑‍🔬

“If we have data, let’s look at the data. If all we have are opinions — let’s go with mine.”- Jim Barksdale, former CEO of Netscape

You should be connected with essential data every day. Data unlocks long-tail insights, highlights opportunities, and problem areas, and empowers product and strategic decisions.

Have data to support any decisions so your team and stakeholders can get aligned. Opinions will likely differ between your team, and you don’t want your argument to rely on personal preferences with little (or no) supporting evidence.

#12 Use product judgment 🧭

The crucial role of data and analytics can’t be overstated. Still, it’s not the end all be all.

Product judgment doesn’t come from just having product experience. Rather, it comes from having specific experience with this product and a deep understanding of this customer and their problems.

Data is indicative and suggestive, it should always be considered — but it needs to be blended with human judgment too.

Sometimes big bets made by product judgment against the data pay-off. Take the iPhone or Facebook Newsfeed, for example.

These are a just few of lessons I’ve learned. To allow yourself to maximize your learning in whatever role you find yourself, you always need to be extremely receptive to feedback, actively pursuing it, and make sure you’re thinking critically and asking the right questions. A fantastic framework here is Socratic Questioning.

Have any thoughts, questions or feedback? 👇

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Every week, I write about product, startups, growth, working with people, and anything else that I’ve found helps me have a happier and more meaningful career in product management

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