Product Management

Main Challenge As A Product Manager

Someone approached me on my LinkedIn and asked the following question: “What do you see the main challenge as a product manager and how do you advise me to overcome it?”

I gave the person a brief answer, but later on, I figured I should probably expand it. Here it goes.

There’s more than one challenge, but since not all challenges are created equal – let’s start in some sort of priority and let’s limit this list to three man challenges.

The first challenge for a product manager is their ability to listen and comprehend what their clients are saying. I’ve seen many PMs that “know better”. While they are still experts in the domain the failure to listen had resulted in failure to launch. Not because the product itself was bad – but because it became a solution looking for a problem instead of a solution for a known problem. Yet, they insisted – even after being presented with the hard evidence – that they know better.

The second challenge is to prioritize things. In many cases instead of prioritization based on customer’s pain points or specific goals the product manager prioritizes things that are dear to her (him) for whatever reason – because she was the one who proposed those features or she’s the biggest advocate of those features. It doesn’t result in major issues for the product, but could be fatal to relationships with customers. When customers see that no matter how many times they ask – they don’t get what they want, they will leave.

The third challenge is to be able to pivot or turn on a dime. Another way to express this is to “fail fast”. This topic alone has books written on it, yet people still manage to hold on to failing ideas because they’re so dear to them that they wouldn’t let go. The ability to fail fast: that is to try the idea and if it’s not working – dropping it and moving on – is still foreign to some people. Occasionally (but only occasionally) the problem stems from people being a “one-trick pony” and their concern (often justified) that they have nothing going for them if they’ve got nothing else. It is understandable but then these people aren’t in the right role for them. Product management is, probably, one of the very few creative roles within the classic enterprise organizations.
Alternatively, some product managers don’t fail fast enough because in their eyes the benefits outweigh the increasing spend (of all resources), when in fact it does not. Usually, this understanding comes with experience, but in a lot of cases, it is not hard to spot.

Ultimately, the three challenges: listening, prioritizing and pivoting fast are not unique to product managers alone – they are common for organizations as well. There’s a notion to call a product manager “a CEO of a product”, so in this case it is actually true – and the product manager is expected to be as wise as a CEO.

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Starting Up In Product Management While Eyeing Own Startup

Question: “Is it better to start off as a software engineer or as a product manager if you want to pursue your own startup in the future?

You won’t be able to start off as a product manager (in a true sense of PdM responsibilities and experience, not in a title) since this role requires having a lot of experience from various disciplines. Product management (again, true responsibilities, not a title) is a multi-disciplinary field that requires a healthy mix of product building experience, technical knowledge, user experience understanding, design knowledge, and marketing expertise. These are not the things that people come to the table with right out of college or grad school – in fact, not many get to build these over time. In fact, I worked with many “product managers” who were stuck in one of the areas they felt comfortable with and not dared to venture into others. This would almost always make them very good in that particular area (say – technology), but rarely makes them good product managers.

With that said, if you are targeting your own startup in the future I think you better off coming from a different angle. Start off as a sales engineer or sales rep.


Because ultimately, no matter what you do in your startup, the only real metric of your success would be the sales figures. Even if the only thing you would have sold is your startup to another company – sales is probably the most important part of product life cycle.

As a sales rep/engineer you get an unfettered access to clients, their pains, wants and needs. You get first-hand accounts of pains and issues your clients want to solve using your product. This way you can be sure your product isn’t a “solution looking for a problem to solve”, but a true pain relief.

It’s very easy to justify NOT talking to your clients as a product manager because you’re too busy or whatnot. I’ve heard this pretty much from every single product owner and product manager (and I am myself was briefly guilty of this) – “I am too important and too busy to talk to customers”. Everyone has to grow up and out of this mindset. If you come to your startup already out of this mindset – you will have a greater chance of success. As a sales engineer or sales rep you don’t have a way to get out of talking to your customers – it’s your job.

As an insight – almost everyone with responsibilities of Director or VP of Product has sales metrics as part of their core KPIs. As a startup founder (or one of them) and a person who envisions and creates the product (assuming you’re eyeing a product startup) you would be responsible for product’s success. Unless you’re giving it away (and even in that case) – your main measure of success would be the number of customers. Being able to sell your product is a huge part of Product Manager (and above) responsibilities. If you are planning to start up your own venture, the ability to sell is probably just as essential as the ability to read, write and create PowerPoint slides.

TL;DR: start as a sales engineer.

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What types of skills are needed to become a Product Manager?

First and foremost is called “critical thinking”. You’d be surprised at the number of people with titles of Product Manager (or, even, Senior Product Manager!) who are lacking this skill.

Another good skill to have is what recruiters like to call “business acumen”. Not sure if they know what it means, but in the classic sense – as in “keenness and quickness in understanding and dealing with a business situation” (source: Wikipedia – Business Acumen) it’s an amazing skill to have. Among other things it allows you to quickly evaluate your own product from a market’s perception and understand if you have a “solution for a problem” or a “solution looking for a problem”. You want to have the former and avoid the latter.

Being able to question everything. Especially – do question the set ways to do things – this is mostly where most of the problems are. Failure is a journey too. If a “user” experiences a certain “pain” – he/she will definitely try and resolve it. When they fail – at least a couple of times – they will hire someone passive enough to “do as they told” and “be quiet” and “not to argue with the boss”. That’s how “ways to do things” are set. That’s how you get people running hundred rep call center from a spreadsheet. That’s how you get people to stop question their commission payments because “no one can analyze hundreds of thousands of rows each month in a single Excel spreadsheet”.

Because “reasons”.

Knowing your technology, what is possible or not possible, or having subject matter experts available. I had a lot of experience developing regular software so I could easily anticipate what can be done and what cannot. When paired with the questioning of the “ways to do things” – it may seem like magic to your customers. A real-life anecdote: “No one was ever able to reconcile these commissions automatically and we can’t do it manually either – these Excel files are huge and have to be downloaded monthly by hand from a password protected portal”. – “What if I can automate the download and import the data into a database. Can I match this against that automatically?” – “I don’t see why not” – “Then we can 100% automate your reconciliation”. – “Wait, what?”

Learning skill. This is probably the most important. In your journey as a product manager, you inevitably will end up with a problem which will not be solved using your existing skill set. You will need to learn something new. This will happen constantly, the more areas of your customers’ lives you will touch. Within 2 years of my previous job, I’ve learned a ton of new stuff. How informal negotiations work. How salespeople talk to customers behind closed doors. What do CEOs talk to each other about and how when they’re partying. How partners in a business fight and how they find ways to resolve their conflicts with minimal impact to the business – and how they fail to maintain the resolution. And, ultimately, how each of these factors affected my own product and its journey.

All others are important too – a product manager is a CEO without a company, so in almost all cases you can’t just delegate the task to someone else. Especially in early stages of building the product you get to do EVERYTHING yourself. Marketing collateral, managing developers, juggling projects, negotiating resources and timelines, hell – sometimes you end up building your product website in a spare time because no one else can build a website for something that doesn’t exist.

Last, but not least that I wanted to mention is the ability to go on. “It’s the courage to continue that counts” and in the world of product management it is the only way to build useful and successful products. Within one year I have tried to create at least a dozen products that solve one problem or another. Nine of them failed completely. One produced a freebie that was great for retention but didn’t make any money for the company directly. One failed, but from the salvaged parts the company was able to build a completely new line of business that became pretty successful. Another one (potentially – as I am not with the said company anymore) is another new successful line of business. What if I had stopped after the first three failures? What about six? If you think you need to draw the line – you don’t. You just keep going.